Organic light-emitting devices

Abstract

The present invention provides an organic light emitting device with improved driving voltage, efficiency and lifetime.

Description

[Technical Field]

[0001] The present invention relates to an organic light-emitting device with improved driving voltage, efficiency and lifetime. [Cross-reference to related applications] This application claims the benefit of priority based on Korean Patent Application No. 10-2022-0002929 filed January 7, 2022 and Korean Patent Application No. 10-2023-0001789 filed January 5, 2023, and all contents disclosed in the documents of said Korean patent applications are incorporated herein by reference. [Background technology]

[0002] Generally, organic light emitting phenomenon refers to a phenomenon in which electrical energy is converted into light energy using organic materials. Organic light emitting devices utilizing organic light emitting phenomenon have a wide viewing angle, excellent contrast, fast response time, and excellent brightness, driving voltage, and response speed characteristics, and are the subject of much research.

[0003] Organic light-emitting devices generally have a structure including an anode, an anode, and an organic material layer between the anode and the cathode. To enhance the efficiency and safety of organic light-emitting devices, the organic material layer often has a multi-layer structure composed of different materials, such as a hole injection layer, a hole transport layer, an emission layer, an electron transport layer, and an electron injection layer. When a voltage is applied between the two electrodes in such an organic light-emitting device, holes are injected into the organic material layer from the anode and electrons are injected into the organic material layer from the cathode. When the injected holes and electrons meet, excitons are formed, and the excitons emit light when they return to their ground state.

[0004] There is a continuous demand for the development of new organic materials for use in such organic light emitting devices. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] Korean Patent Publication No. 10-2000-0051826 Summary of the Invention [Problem to be solved by the invention]

[0006] The present invention relates to an organic light-emitting device with improved driving voltage, efficiency and lifetime. [Means for solving the problem]

[0007] The present invention provides an organic light-emitting device comprising: a positive electrode; a negative electrode; and a light-emitting layer between the positive electrode and the negative electrode, The light-emitting layer comprises at least one compound represented by the following Chemical Formula 1: One or more compounds represented by the following chemical formula 2: and Contains one or more compounds represented by the following chemical formula 3: Organic light-emitting devices:

[0008] [ka] In the above Chemical Formula 1, Ar1 and Ar2 each independently represent a substituted or unsubstituted aryl having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms containing at least one selected from the group consisting of N, O, and S; L1 to L3 each independently represent a single bond; or a substituted or unsubstituted arylene having 6 to 60 carbon atoms, R1 each independently represents hydrogen; deuterium; a substituted or unsubstituted aryl having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms containing at least one selected from the group consisting of N, O, and S; a is an integer from 0 to 7,

[0009] [ka] In the above Chemical Formula 2, X'1 is N and X'2 is O; or X'1 is O and X'2 is N, any one of R'1 to R'7 is linked to the following Chemical Formula 2A, and the rest are each independently hydrogen; deuterium; a substituted or unsubstituted aryl having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms containing at least one selected from the group consisting of N, O, and S;

[0010] [ka] In the chemical formula 2A, L'1 to L'3 each independently represent a single bond; or a substituted or unsubstituted arylene having 6 to 60 carbon atoms, Ar'1 and Ar'2 each independently represent a substituted or unsubstituted aryl having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms containing at least one selected from the group consisting of N, O, and S;

[0011] [ka] In the above Chemical Formula 3, X" is O or S, R”1~R” 10 is linked to the following chemical formula 3A, and the rest are hydrogen or deuterium, [ka] In the above Chemical Formula 3A, L"1 to L"3 each independently represent a single bond; or a substituted or unsubstituted arylene having 6 to 60 carbon atoms, Ar"1 and Ar"2 are each independently a substituted or unsubstituted aryl having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms containing at least one selected from the group consisting of N, O, and S. [Effects of the Invention]

[0012] The above-mentioned organic light emitting device includes, in the light emitting layer, one or more of the compounds represented by Chemical Formula 1, one or more of the compounds represented by Chemical Formula 2, and one or more of the compounds represented by Chemical Formula 3, thereby improving the efficiency, lowering the driving voltage, and / or improving the life characteristics of the organic light emitting device. [Brief explanation of the drawings]

[0013] [Figure 1] The figure shows an example of an organic light-emitting device comprising a substrate 1, a positive electrode 2, a light-emitting layer 3, and a negative electrode 4. [Figure 2] 1 shows an example of an organic light-emitting device comprising a substrate 1, a positive electrode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light-emitting layer 3, a hole blocking layer 8, an electron injection and transport layer 9, and a negative electrode 4. DETAILED DESCRIPTION OF THE INVENTION

[0014] The present invention will be explained in more detail below for better understanding.

[0015] In this specification, [ka] denotes a bond that is connected to another substituent.

[0016] As used herein, the term "substituted or unsubstituted" refers to a group selected from the group consisting of deuterium, halogen, nitrile, nitro, hydroxy, carbonyl, ester, imide, amino, phosphine oxide, alkoxy, aryloxy, alkylthioxy, arylthioxy, alkylsulfoxy, arylsulfoxy, silyl, boron, alkyl, cycloalkyl, alkenyl, aryl, aralkyl, aralkenyl, alkylaryl, alkylamine, aralkylamine, heteroarylamine, arylamine, arylphosphine, or heterocyclic groups containing one or more N, O, and S atoms, and may refer to a group in which two or more of the above-listed substituents are linked together. For example, a "substituent having two or more linked substituents" may be a biphenyl group. That is, a biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are linked together.

[0017] In this specification, the number of carbon atoms of the carbonyl group is not particularly limited, but preferably is 1 to 40. Specifically, the carbonyl group may be a substituent having the structure shown below, but is not limited thereto. [ka]

[0018] In this specification, the oxygen of the ester group may be substituted with a linear, branched, or cyclic alkyl group having 1 to 25 carbon atoms, or an aryl group having 6 to 25 carbon atoms. Specific examples include, but are not limited to, substituents having the following structural formulas: [ka]

[0019] In this specification, the number of carbon atoms in the imide group is not particularly limited, but is preferably 1 to 25. Specific examples include, but are not limited to, substituents having the structures shown below. [ka]

[0020] In this specification, specific examples of silyl groups include, but are not limited to, trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, and phenylsilyl groups.

[0021] In this specification, specific examples of the boron group include, but are not limited to, a trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, and a phenyl boron group.

[0022] As used herein, examples of halogen groups include fluorine, chlorine, bromine, or iodine.

[0023] In this specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the number of carbon atoms in the alkyl group is 1 to 20. According to another embodiment, the number of carbon atoms in the alkyl group is 1 to 10. According to another embodiment, the number of carbon atoms in the alkyl group is 1 to 6. Specific examples of alkyl groups include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-gal, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1-dimethylpropyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like.

[0024] In this specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms in the alkenyl group is 2 to 20. According to another embodiment, the number of carbon atoms in the alkenyl group is 2 to 10. According to another embodiment, the number of carbon atoms in the alkenyl group is 2 to 6. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, a stilbenyl group, and a styrenyl group, but are not limited to these.

[0025] In this specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specific examples include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, and cyclooctyl.

[0026] In this specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. Examples of the monocyclic aryl group include, but are not limited to, a phenyl group, a biphenyl group, and a terphenyl group. Examples of the polycyclic aryl group include, but are not limited to, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a chrysenyl group, and a fluorenyl group.

[0027] In this specification, the fluorenyl group may be substituted, and two of the substituents may be bonded to each other to form a spiro structure. When the fluorenyl group is substituted, [ka] However, the present invention is not limited to this.

[0028] In this specification, the heterocyclic group is a heterocyclic group containing one or more heteroelements selected from O, N, Si and S, and is not particularly limited in number of carbon atoms, but preferably has 2 to 60 carbon atoms. Examples of heterocyclic groups include, but are not limited to, thiophene, furan, pyrrole, imidazole, thiazole, oxazole, oxadiazole, triazole, pyridyl, bipyridyl, pyrimidine, triazine, acridyl, pyridazine, pyrazinyl, quinolinyl, quinazoline, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinoline, indole, carbazole, benzoxazole, benzimidazole, benzothiazole, benzocarbazole, benzothiophene, dibenzothiophene, benzofuranyl, phenanthroline, isoxazolyl, thiadiazolyl, phenothiazinyl, and dibenzofuranyl groups.

[0029] In this specification, the aryl group in the aralkyl group, aralkenyl group, alkylaryl group, and arylamine group is the same as the aryl group exemplified above. In this specification, the alkyl group in the aralkyl group, alkylaryl group, and alkylamine group is the same as the alkyl group exemplified above. In this specification, the heteroaryl in the heteroarylamine can be applied to the heteroaryl group described above. In this specification, the alkenyl group in the aralkenyl group is the same as the alkenyl group exemplified above. In this specification, the aryl group described above can be applied to the arylene group, except that it is a divalent group. In this specification, the heterocyclic group described above can be applied to the heteroarylene group, except that it is a divalent group. In this specification, the aryl group or cycloalkyl group described above can be applied to the hydrocarbon ring, except that it is not a monovalent group but is formed by bonding two substituents. In this specification, the heterocyclic group described above can be applied to the heterocycle group, except that it is not a monovalent group but is formed by bonding two substituents.

[0030] On the other hand, when we want to express the number of deuterium substitutions of a specific compound in this specification, we use the formula "[Structural formula] Dn " Here, "Dn" means that n hydrogen atoms in the compound represented by the "structural formula" have been replaced with deuterium atoms.

[0031] The present invention will be described in detail below for each component.

[0032] Positive and negative electrodes The positive electrode and negative electrode used in the present invention refer to electrodes used in an organic light-emitting device.

[0033] The cathode material preferably has a high work function to facilitate hole injection into the organic layer. Specific examples of the cathode material include, but are not limited to, metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline.

[0034] The negative electrode material is preferably a material with a small work function to facilitate electron injection into the organic layer. Specific examples of the negative electrode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; and multilayer structures such as LiF / Al or LiO / Al.

[0035] hole injection layer The organic light emitting device according to the present invention may further include a hole injection layer on the anode, if necessary.

[0036] The hole injection layer is a layer that injects holes from the electrode. The hole injection material preferably has the ability to transport holes, thereby providing excellent hole injection effect in the cathode, the light-emitting layer, or the light-emitting material, preventing the migration of excitons generated in the light-emitting layer to the electron injection layer or the electron injection material, and excellent thin-film formation ability. Furthermore, it is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material be between the work function of the cathode material and the HOMO of the surrounding organic layer.

[0037] Specific examples of hole injection materials include, but are not limited to, metal porphyrin, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, perylene-based organic materials, anthraquinone, and polyaniline and polythiophene-based conductive polymers.

[0038] hole transport layer The organic light-emitting device according to the present invention may optionally include a hole transport layer on the anode (or on the hole injection layer if the hole injection layer is present).

[0039] The hole transport layer receives holes from the anode or the hole injection layer and transports them to the light emitting layer. As the hole transport material, a material that can receive holes from the anode or the hole injection layer and transfer them to the light emitting layer and has high mobility for holes is suitable.

[0040] Specific examples of the hole transport material include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers having both conjugated and non-conjugated portions.

[0041] Electron Blocking Layer The organic light emitting device according to the present invention may optionally include an electron blocking layer on the hole transport layer.

[0042] The electron blocking layer is a layer disposed between the hole transport layer and the light emitting layer to prevent electrons injected from the anode from passing to the hole transport layer without recombining in the light emitting layer, and is also called an electron blocking layer or an electron inhibiting layer. The electron blocking layer is preferably made of a material having a smaller electron affinity than the electron transport layer.

[0043] Light-emitting layer The light-emitting layer used in the present invention refers to a layer capable of emitting light in the visible light region by combining holes and electrons transferred from the positive electrode and the negative electrode. Generally, the light-emitting layer includes a host material and a dopant material, and in the present invention, the light-emitting layer includes one or more of the compounds represented by Chemical Formula 1, one or more of the compounds represented by Chemical Formula 2, and one or more of the compounds represented by Chemical Formula 3 as hosts.

[0044] Preferably, the compound represented by Chemical Formula 1 can be represented by any one of the following Chemical Formulas 1-1 to 1-3: [ka]

[0045] In the above chemical formulas 1-1 to 1-3, Ar1, Ar2, and L1 to L3 are as defined in Chemical Formula 1; R1 is deuterium; a substituted or unsubstituted aryl having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms and containing at least one selected from the group consisting of N, O, and S.

[0046] Preferably, Ar1 and Ar2 are each independently a substituted or unsubstituted aryl having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroaryl having 2 to 20 carbon atoms containing at least one selected from the group consisting of N, O, and S, More preferably, Ar1 and Ar2 may each independently be phenyl, triphenylsilylphenyl, biphenylyl, terphenylyl, naphthyl, phenanthrenyl, chrysenyl, benzo[c]phenanthrenyl, dibenzofuranyl, or dibenzothiophenyl, and Ar1 and Ar2 may each independently be unsubstituted or substituted with one or more deuterium atoms.

[0047] Most preferably, Ar1 and Ar2 may each independently be any one selected from the group consisting of the following, wherein the hydrogen of each substituent in the following group can each independently be replaced with deuterium: [ka]

[0048] Preferably, L1 to L3 each independently represent a single bond; or a substituted or unsubstituted arylene having 6 to 20 carbon atoms, More preferably, L1 to L3 may each independently represent a single bond, phenylene, biphenyldiyl, naphthalenediyl, phenylnaphthalenediyl, or naphthylnaphthalenediyl, and when L1 to L3 are phenylene, biphenyldiyl, naphthalenediyl, phenylnaphthalenediyl, or naphthylnaphthalenediyl, L1 to L3 may be unsubstituted or substituted with one or more deuterium atoms; Most preferably, L1 to L3 may each independently represent a single bond or any one selected from the group consisting of the following, in which hydrogen in each linker may independently be replaced with deuterium: [ka]

[0049] Preferably, each R1 may independently represent hydrogen; deuterium; a substituted or unsubstituted aryl having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroaryl having 2 to 20 carbon atoms containing at least one selected from the group consisting of N, O, and S; More preferably, each R1 may independently be hydrogen, deuterium, phenyl, biphenylyl, terphenylyl, naphthyl, phenanthrenyl, triphenylenyl, naphthylphenyl, phenylnaphthyl, fluoranthenyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, or benzonaphthothiophenyl. When R1 is phenyl, biphenylyl, terphenylyl, naphthyl, phenanthrenyl, triphenylenyl, naphthylphenyl, phenylnaphthyl, fluoranthenyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, or benzonaphthothiophenyl, each R1 may independently be unsubstituted or substituted with one or more deuterium atoms.

[0050] Preferably, at least one of Ar1, Ar2 and R1 may be phenyl, naphthyl, phenylnaphthyl, naphthylphenyl, phenanthrenyl, fluoranthenyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, or benzonaphthothiophenyl, and each of Ar1, Ar2 and R1 may independently be unsubstituted or substituted with one or more deuterium atoms.

[0051] More preferably, at least one of Ar1, Ar2 and R1 may be phenyl, naphthyl, phenylnaphthyl, naphthylphenyl, fluoranthenyl, dibenzofuranyl, benzonaphthofuranyl, or benzonaphthothiophenyl, and each of Ar1, Ar2 and R1 may independently be unsubstituted or substituted with one or more deuterium atoms.

[0052] Preferably, a can be 0 or 1. More preferably, a can be 1.

[0053] Meanwhile, the number of deuterium substitutions of the compound can be expressed by the following chemical formula 1D: [ka] In the above Chemical Formula 1D, Dn means that n hydrogens have been replaced by deuterium. where n is an integer equal to or greater than 13, Ar 1d , Ar 2d , L 1d ~L 3d are each substituted with deuterium or represent Ar1, Ar2, L1 to L3 substituents, R 1d is a substituted or unsubstituted aryl having 6 to 60 carbon atoms that is not substituted with deuterium; or a substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms that contains at least one selected from the group consisting of N, O, and S that is not substituted with deuterium, a is an integer from 0 to 7.

[0054] For example, in Chemical Formula 1D, n in Dn may be 13 or more, 14 or more, 15 or more, 16 or more, 17 or more, 18 or more, or 19 or more, and may be 50 or less, 45 or less, 40 or less, 38 or less, 36 or less, 34 or less, 32 or less, 30 or less, 28 or less, 26 or less, 24 or less, 23 or less, 22 or less, 21 or less, or 20 or less.

[0055] Representative examples of the compound represented by Formula 1 are as follows:

[0056] [ka]

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[0337] Among the compounds represented by Chemical Formula 1, when R1 is hydrogen or deuterium, the compound can be prepared, for example, by a preparation method such as the following Reaction Scheme 1-1. When R1 is not hydrogen or deuterium, the compound can be prepared, for example, by a preparation method such as the following Reaction Scheme 1-2. Other compounds can also be prepared in a similar manner.

[0338] [ka] In the reaction formulas 1-1 and 1-2, Ar1, Ar2 and L1 to L3 are as defined in the chemical formula 1, and Z1 to Z3 are halogen, preferably chloro or bromo.

[0339] The above-mentioned Reaction Schemes 1-1 and 1-2 are Suzuki coupling reactions, which are preferably carried out in the presence of a palladium catalyst and a base, and the reactive groups for the Suzuki coupling reaction can be varied as known in the art. The above-mentioned preparation methods can be further embodied in the preparation examples described below.

[0340] Preferably, the compound represented by Chemical Formula 2 can be represented by either Chemical Formula 2-1 or Chemical Formula 2-2 below:

[0341] [ka] In the above Chemical Formula 2-1 and Chemical Formula 2-2, R'1 to R'6 are hydrogen or deuterium; R'7 is a substituted or unsubstituted aryl having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms containing at least one selected from the group consisting of N, O, and S, X'1, X'2, L'1 to L'3, Ar'1 and Ar'2 are as defined above.

[0342] Preferably, any one of R'1 to R'7 is linked to Formula 2A, and the rest are each independently hydrogen; deuterium; a substituted or unsubstituted aryl having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroaryl having 2 to 20 carbon atoms containing at least one selected from the group consisting of N, O, and S.

[0343] More preferably, any one of R'1 to R'7 is represented by Formula 2A, and the rest may each independently be hydrogen, deuterium, phenyl, biphenylyl, or naphthyl, and the phenyl, biphenylyl, and naphthyl may each independently be unsubstituted or substituted with one or more deuterium atoms.

[0344] Preferably, L'1 to L'3 each independently represent a single bond; or a substituted or unsubstituted arylene having 6 to 20 carbon atoms, More preferably, L'1 to L'3 may each independently be a single bond, phenylene, biphenyldiyl, terphenyldiyl, naphthalenediyl, or phenylnaphthalenediyl, and the phenylene, biphenyldiyl, terphenyldiyl, naphthalenediyl, and phenylnaphthalenediyl may each independently be unsubstituted or substituted with one or more deuterium atoms.

[0345] Preferably, Ar'1 and Ar'2 may each independently represent a substituted or unsubstituted aryl having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroaryl having 2 to 20 carbon atoms containing at least one selected from the group consisting of N, O, and S, More preferably, Ar'1 and Ar'2 may each independently be phenyl, biphenylyl, terphenylyl, naphthyl, phenylnaphthyl, phenanthrenyl, dimethylfluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, or phenylcarbazolyl, and said Ar'1 and Ar'2 may be unsubstituted or substituted with one or more deuterium atoms.

[0346] Representative examples of the compound represented by Formula 2 are as follows:

[0347] [ka]

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[0479] The compound represented by Chemical Formula 2 can be prepared by the following method as shown in Reaction Scheme 2-1 when L'1 is not a single bond, and by the following method as shown in Reaction Scheme 2-2 when L'1 is a single bond. Other compounds can also be prepared in a similar manner.

[0480] [ka]

[0481] In the reaction formulas 2-1 and 2-2, R'1 to R'6, X'1, X'2, Ar'1, Ar'2, and L'1 to L'3 are as defined in the chemical formulas 2 and 2A, and Z'1 and Z'2 are halogen, preferably, Z'1 and Z'2 are chloro or bromo.

[0482] Reaction Scheme 2-1 is a Suzuki coupling reaction, preferably carried out in the presence of a palladium catalyst and a base, and the reactive groups for the Suzuki coupling reaction may be varied as known in the art. Reaction Scheme 2-2 is an amine substitution reaction, preferably carried out in the presence of a palladium catalyst and a base, and the reactive groups for the amine substitution reaction may be varied as known in the art. The preparation method can be further embodied in the preparation examples described below.

[0483] Preferably, the chemical formula 3A is R″1, R″2, R″4, R″5 and R″8 to R″1 of the chemical formula 3. 10 It is connected to one of the following.

[0484] Preferably, L"1 to L"3 each independently represent a single bond; or a substituted or unsubstituted arylene having 6 to 20 carbon atoms, More preferably, L"1 to L"3 may each independently be a single bond, phenylene, biphenyldiyl, naphthalenediyl, or dimethylfluorenediyl, and the phenylene, biphenyldiyl, naphthalenediyl, and dimethylfluorenediyl may each independently be unsubstituted or substituted with one or more deuterium atoms.

[0485] Preferably, Ar"1 and Ar"2 are each independently a substituted or unsubstituted aryl having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroaryl having 2 to 20 carbon atoms containing at least one selected from the group consisting of N, O, and S, More preferably, Ar"1 and Ar"2 may each independently be phenyl, triphenylsilylphenyl, biphenylyl, terphenylyl, naphthyl, phenanthrenyl, dimethylfluorenyl, spirobifluorenyl, dibenzofuranyl, dibenzothiophenyl, or phenylcarbazolyl, and Ar"1 and Ar"2 may each independently be unsubstituted or substituted with one or more deuterium atoms.

[0486] Representative examples of the compound represented by Formula 3 are as follows:

[0487] [ka]

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[0720] [ka] The compound represented by Chemical Formula 3 can be, for example, a compound represented by Chemical Formula 3A, wherein R 10 When L"1 is not a single bond, it can be prepared by the preparation method shown in the following reaction formula 3-1. 10 When L"1 is a single bond, it can be prepared by the method shown in the following reaction scheme 3-2, and other compounds can be prepared in a similar manner.

[0721] [ka]

[0722] In the reaction formulas 3-1 and 3-2, R"1 to R"9, X", Ar"1, Ar"2, and L"1 to L"3 are as defined in the chemical formulas 3 and 3A, and Z"1 and Z"2 are halogen, preferably chloro or bromo.

[0723] Reaction Scheme 3-1 is a Suzuki coupling reaction, preferably carried out in the presence of a palladium catalyst and a base, and the reactive groups for the Suzuki coupling reaction may be varied as known in the art. Reaction Scheme 3-2 is an amine substitution reaction, preferably carried out in the presence of a palladium catalyst and a base, and the reactive groups for the amine substitution reaction may be varied as known in the art. The preparation method can be further embodied in the preparation examples described below.

[0724] Preferably, in the light-emitting layer, the weight ratio of the compound represented by Chemical Formula 1 to the compound represented by Chemical Formula 2 is 10:90 to 90:10, more preferably 20:80 to 80:20, 30:70 to 70:30, or 40:60 to 60:40.

[0725] More preferably, in the light-emitting layer, the weight ratio of the compound represented by Chemical Formula 1 to the compound represented by Chemical Formula 3 is 10:90 to 90:10, and more preferably 20:80 to 80:20, 30:70 to 70:30, or 40:60 to 60:40.

[0726] Meanwhile, the light-emitting layer may further include a dopant in addition to the host. The dopant material is not particularly limited as long as it is a material used in organic light-emitting devices. Examples of the dopant include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, aromatic amine derivatives include fused aromatic ring derivatives having a substituted or unsubstituted arylamino group, such as pyrene, anthracene, chrysene, and periflanthene, each of which has an arylamino group. Styrylamine compounds include substituted or unsubstituted arylamines substituted with at least one arylvinyl group, and may be substituted or unsubstituted with one or more substituents selected from the group consisting of aryl groups, silyl groups, alkyl groups, cycloalkyl groups, and arylamino groups. Specific examples include, but are not limited to, styrylamines, styryldiamines, styryltriamines, and styryltetraamines. Metal complexes include, but are not limited to, iridium complexes and platinum complexes.

[0727] hole-blocking layer The organic light-emitting device according to the present invention may optionally include an electron transport layer on the light-emitting layer.

[0728] The hole blocking layer is a layer disposed between the electron transport layer and the light emitting layer to prevent holes injected from the positive electrode from passing to the electron transport layer without being recombined in the light emitting layer, and is also called a hole inhibiting layer or hole blocking layer. A material with high ionization energy is preferred for the hole blocking layer.

[0729] electron transport layer The organic light-emitting device according to the present invention may optionally include an electron transport layer on the light-emitting layer.

[0730] The electron transport layer receives electrons from the anode or the electron injection layer formed on the anode, transports the electrons to the light-emitting layer, and suppresses the transport of holes in the light-emitting layer. As the electron transport material, a material that can efficiently receive electrons injected from the anode and transfer them to the light-emitting layer and has high electron mobility is suitable.

[0731] Specific examples of the electron transport material include, but are not limited to, Al complexes of 8-hydroxyquinoline; complexes containing Alq; organic radical compounds; and hydroxyflavone-metal complexes. The electron transport layer can be used with any desired cathode material, as used in conventional technology. In particular, examples of suitable cathode materials are conventional materials with low work functions followed by an aluminum or silver layer. Specific examples include cesium, barium, calcium, ytterbium, and samarium, each followed by an aluminum or silver layer.

[0732] electron injection layer The organic light emitting device according to the present invention may further include an electron injection layer on the light emitting layer (or on the electron transport layer, if present) as needed.

[0733] The electron injection layer is a layer that injects electrons from the electrode, and it is preferable to use a compound that has the ability to transport electrons, has an excellent electron injection effect from the negative electrode, has an excellent electron injection effect on the light-emitting layer or the light-emitting material, prevents excitons generated in the light-emitting layer from moving to the hole injection layer, and has excellent thin-film formation ability.

[0734] Specific examples of materials that can be used in the electron injection layer include, but are not limited to, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, preolenylidenemethane, anthrone, and derivatives thereof, metal complex compounds, and nitrogen-containing five-membered ring derivatives thereof.

[0735] Examples of the metal complex compounds include, but are not limited to, 8-hydroxyquinolinatolithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h]quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)(o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, and bis(2-methyl-8-quinolinato)(2-naphtholato)gallium.

[0736] Meanwhile, in the present invention, the "electron injection and transport layer" refers to a layer that functions both as the electron injection layer and the electron transport layer, and materials that function as the respective layers may be used alone or in combination, but are not limited thereto.

[0737] Organic light-emitting devices The structures of organic light-emitting devices according to the present invention are illustrated in Figures 1 and 2. Figure 1 shows an example of an organic light-emitting device comprising a substrate 1, a positive electrode 2, a light-emitting layer 3, and a negative electrode 4. Figure 2 shows an example of an organic light-emitting device comprising a substrate 1, a positive electrode 2, a hole-injection layer 5, a hole-transport layer 6, an electron-blocking layer 7, a light-emitting layer 3, a hole-blocking layer 8, an electron-injection and transport layer 9, and a negative electrode 4.

[0738] The organic light-emitting device according to the present invention can be fabricated by sequentially stacking the above components. To do this, a metal, conductive metal oxide, or alloy thereof can be deposited on a substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation to form the cathode. The above layers can then be formed on top of that, and a material suitable for the anode can then be deposited on top of that. Alternatively, an organic light-emitting device can be fabricated by sequentially depositing the cathode material on a substrate in the reverse order of the above-described structure (WO 2003 / 012890). The light-emitting layer can be formed by depositing the host and dopant using a solution coating method, as well as vacuum deposition. Solution coating methods include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, and roll coating.

[0739] Meanwhile, the organic light emitting device according to the present invention may be a bottom emission device, a top emission device, or a double-sided emission device, and may particularly be a bottom emission device which requires relatively high luminous efficiency.

[0740] Preferred examples are presented below for better understanding of the present invention. However, the following examples are provided for easier understanding of the present invention and are not intended to limit the scope of the present invention.

[0741] Synthesis Example 1-1 [ka]

[0742] (2-chlorodibenzo[b,d]furan-1-yl)boronic acid (15 g, 60.9 mmol) and compound Trz1 (26.7 g, 63.9 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (25.2 g, 182.6 mmol) dissolved in 76 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 3 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 24.5 g of compound 1-1_P1. (Yield: 69%, MS: [M+H] + =584)

[0743] Compound 1-1_P1 (15 g, 25.7 mmol) and naphthalen-2-ylboronic acid (4.6 g, 27 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (10.6 g, 77 mmol) dissolved in 32 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 3 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.1 g of compound 1-1. (Yield 70%, MS: [M+H] + =676)

[0744] Synthesis Example 1-2 [ka]

[0745] (2-chlorodibenzo[b,d]furan-1-yl)boronic acid (15 g, 60.9 mmol) and compound Trz2 (30.9 g, 63.9 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (25.2 g, 182.6 mmol) dissolved in 76 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 2 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 26.5 g of compound 1-2_P1. (Yield: 67%, MS: [M+H] + =650)

[0746] Compound 1-2_P1 (15 g, 23.1 mmol) and dibenzo[b,d]furan-2-ylboronic acid (5.1 g, 24.2 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (9.6 g, 69.2 mmol) dissolved in 29 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 2 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 13.2 g of compound 1-2. (Yield 73%, MS: [M+H] + =782)

[0747] Synthesis Example 1-3 [ka]

[0748] (2-chlorodibenzo[b,d]furan-1-yl)boronic acid (15 g, 60.9 mmol) and compound Trz3 (27.1 g, 63.9 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (25.2 g, 182.6 mmol) dissolved in 76 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 4 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 23.3 g of compound 1-3_P1. (Yield: 66%, MS: [M+H] + =580)

[0749] Compound 1-3_P1 (15 g, 25.4 mmol) and [1,1'-biphenyl]-4-ylboronic acid (5.3 g, 26.7 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (10.5 g, 76.3 mmol) dissolved in 32 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 5 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 13.5 g of compound 1-3. (Yield 75%, MS: [M+H] + =708)

[0750] Synthesis Example 1-4 [ka]

[0751] (3-chlorodibenzo[b,d]furan-1-yl)boronic acid (15 g, 60.9 mmol) and compound Trz4 (28.4 g, 63.9 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (25.2 g, 182.6 mmol) dissolved in 76 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 3 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 27.4 g of compound 1-4_P1. (Yield 74%, MS: [M+H] + =610)

[0752] Compound 1-4_P1 (15 g, 24.6 mmol) and naphthalen-2-ylboronic acid (4.4 g, 25.8 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (10.2 g, 73.8 mmol) dissolved in 31 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 5 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 11.2 g of compound 1-4. (Yield 65%, MS: [M+H] + =702)

[0753] Synthesis Examples 1-5 [ka]

[0754] (3-chlorodibenzo[b,d]furan-1-yl)boronic acid (15 g, 60.9 mmol) and compound Trz5 (17.1 g, 63.9 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (25.2 g, 182.6 mmol) dissolved in 76 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 3 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 18.7 g of compound 1-5_P1. (Yield 71%, MS: [M+H] + =434)

[0755] Compound 1-5_P1 (15 g, 34.6 mmol) and fluoranthen-3-ylboronic acid (8.9 g, 36.3 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (14.3 g, 103.7 mmol) dissolved in 43 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 4 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 14.9 g of compound 1-5. (Yield 72%, MS: [M+H] + =600)

[0756] Synthesis Examples 1-6 [ka]

[0757] Compound 1-5_P1 (15 g, 34.6 mmol) and naphtho[2,3-b]benzofuran-1-ylboronic acid (9.5 g, 36.3 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (14.3 g, 103.7 mmol) dissolved in 43 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 4 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 13.8 g of compound 1-6. (Yield: 65%, MS: [M+H] + =616)

[0758] Synthesis Example 1-7 [ka]

[0759] (3-chlorodibenzo[b,d]furan-1-yl)boronic acid (15 g, 60.9 mmol) and compound Trz6 (32.9 g, 63.9 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (25.2 g, 182.6 mmol) dissolved in 76 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 4 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 27.4 g of compound 1-7_P1. (Yield 71%, MS: [M+H] + =636)

[0760] Compound 1-7_P1 (15 g, 23.6 mmol) and naphthalen-2-ylboronic acid (4.3 g, 24.8 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (9.8 g, 70.7 mmol) dissolved in 29 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 4 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 11.5 g of compound 1-7. (Yield 67%, MS: [M+H] + =728)

[0761] Synthesis Example 1-8 [ka]

[0762] Trifluoromethanesulfonic anhydride (30.1 g, 106.6 mmol) and deuterium oxide (10.7 g, 532.8 mmol) were added to the mixture at 0°C and stirred for 5 hours to form a solution. 1-bromo-4-chlorodibenzo[b,d]furan (15 g, 53.3 mmol) was added to 120 mL of 1,2,4-trichlorobenzene and stirred. The prepared trifluoromethanesulfonic anhydride and deuterium oxide mixture was then slowly added dropwise to the 1-bromo-4-chlorodibenzo[b,d]furan and 1,2,4-trichlorobenzene mixture, heated to 140°C, and maintained at this temperature while stirring. After reacting for 3 hours, the mixture was cooled to room temperature and the organic and aqueous layers were separated. The organic layer was then neutralized with an aqueous potassium carbonate solution. After washing twice with water, the organic layer was separated, added to anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 6.5 g of compound Sub1-1-1. (Yield: 43%, MS: [M+H] + =283)

[0763] Compound Sub1-1-1 (15 g, 52.9 mmol) and bis(pinacolato)diboron (14.8 g, 58.2 mmol) were refluxed in 300 mL of 1,4-dioxane and stirred. Potassium acetate (7.8 g, 79.4 mmol) was then added and thoroughly stirred. Then, bis(dibenzylideneacetone)palladium(0) (0.9 g, 1.6 mmol) and tricyclohexylphosphine (0.9 g, 3.2 mmol) were added. The mixture was allowed to react for 6 hours, cooled to room temperature, and the organic layer was separated using chloroform and water. The organic layer was then distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 10.8 g of compound Sub1-1-2. (Yield: 62%, MS: [M+H]+ =331)

[0764] Compound Sub1-1-2 (15 g, 45.4 mmol) and compound Trz7 (28.1 g, 47.6 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (18.8 g, 136.1 mmol) dissolved in 56 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After 2 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 23.3 g of compound 1-8_P1. (Yield 72%, MS: [M+H] + =714)

[0765] Compound 1-8_P1 (15 g, 21 mmol) and phenylboronic acid (2.7 g, 22.1 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (8.7 g, 63 mmol) dissolved in 26 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 5 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 10 g of compound 1-8. (Yield 63%, MS: [M+H] + =756)

[0766] Synthesis Example 1-9 [ka]

[0767] Compound Sub1-1-2 (15 g, 45.4 mmol) and compound Trz8 (29.6 g, 47.6 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (18.8 g, 136.1 mmol) dissolved in 56 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After 5 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 25.3 g of compound 1-9_P1. (Yield 75%, MS: [M+H] + =744)

[0768] Compound 1-9_P1 (15 g, 20.2 mmol) and phenylboronic acid (2.6 g, 21.2 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (8.4 g, 60.5 mmol) dissolved in 25 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 5 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 11.1 g of compound 1-9. (Yield 70%, MS: [M+H] + =786)

[0769] Synthesis Example 1-10 [ka]

[0770] Trifluoromethanesulfonic anhydride (60.1 g, 213.1 mmol) and deuterium oxide (21.4 g, 1065.6 mmol) were added at 0°C and stirred for 5 hours to form a solution. 1-bromo-4-chlorodibenzo[b,d]furan (15 g, 53.3 mmol) was added to 120 mL of 1,2,4-trichlorobenzene and stirred. The prepared trifluoromethanesulfonic anhydride and deuterium oxide mixed solution was then slowly added dropwise to the 1-bromo-4-chlorodibenzo[b,d]furan and 1,2,4-trichlorobenzene mixed solution, heated to 140°C, and maintained at this temperature while stirring. After reacting for 10 hours, the mixture was cooled to room temperature and the organic and aqueous layers were separated. The organic layer was then neutralized with an aqueous potassium carbonate solution. After washing twice with water, the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 5.3 g of compound Sub1-2-1. (Yield: 35%, MS: [M+H] + =285)

[0771] Compound Sub1-2-1 (15 g, 52.5 mmol) and bis(pinacolato)diboron (14.7 g, 57.8 mmol) were refluxed in 300 mL of 1,4-dioxane and stirred. Potassium acetate (7.7 g, 78.8 mmol) was then added and thoroughly stirred. Then, bis(dibenzylideneacetone)palladium(0) (0.9 g, 1.6 mmol) and tricyclohexylphosphine (0.9 g, 3.2 mmol) were added. The mixture was allowed to react for 6 hours, cooled to room temperature, and the organic layer was separated using chloroform and water. The organic layer was then distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 11 g of compound Sub1-2-2. (Yield: 63%, MS: [M+H]+ =333)

[0772] Compound Sub1-2-2 (15 g, 45.1 mmol) and compound Trz9 (15.8 g, 47.4 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (18.7 g, 135.3 mmol) dissolved in 56 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After 3 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 14.6 g of compound 1-10_P1. (Yield: 66%, MS: [M+H] + =493)

[0773] Compound 1-10_P1 (15 g, 30.4 mmol) and dibenzo[b,d]furan-1-ylboronic acid (6.8 g, 31.9 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (12.6 g, 91.3 mmol) dissolved in 38 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 13.3 g of compound 1-10. (Yield 70%, MS: [M+H] + =625)

[0774] Synthesis Example 1-11 [ka]

[0775] (3-chlorodibenzo[b,d]furan-1-yl)boronic acid (15 g, 60.9 mmol) and compound Trz10 (25.2 g, 63.9 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (25.2 g, 182.6 mmol) dissolved in 76 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 2 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 21.1 g of compound 1-11_P1. (Yield 62%, MS: [M+H] + =560)

[0776] Compound 1-11_P1 (15 g, 26.8 mmol) and phenylboronic acid (3.4 g, 28.1 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (11.1 g, 80.3 mmol) dissolved in 33 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 2 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 11.8 g of compound 1-11_P2. (Yield 73%, MS: [M+H] + =602)

[0777] Compound 1-11_P2 (10 g, 16.6 mmol), PtO2 (1.1 g, 5 mmol), and 83 ml of DO were placed in a shaker tube, sealed, and heated at 250°C and 600 psi for 12 hours. Upon completion of the reaction, chloroform was added and the reaction mixture was transferred to a separatory funnel for extraction. The extract was dried over MgSO4, concentrated, and the sample was purified by silica gel column chromatography to produce 3.1 g of compound 1-11. (Yield 30%, MS: [M+H] + =626)

[0778] Synthesis Example 1-12 [ka]

[0779] (3-chlorodibenzo[b,d]furan-1-yl)boronic acid (15 g, 60.9 mmol) and compound Trz11 (23.5 g, 63.9 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (25.2 g, 182.6 mmol) dissolved in 76 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 2 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 23.4 g of compound 1-12_P1. (Yield 72%, MS: [M+H] + =534)

[0780] Compound 1-12_P1 (15 g, 28.1 mmol) and dibenzo[b,d]thiophen-4-ylboronic acid (6.7 g, 29.5 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (11.6 g, 84.3 mmol) dissolved in 35 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 4 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, and stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.4 g of compound 1-12_P2. (Yield 65%, MS: [M+H] + =682)

[0781] Compound 1-12_P2 (10 g, 14.7 mmol), PtO2 (1 g, 4.4 mmol), and 73 ml of DO were placed in a shaker tube, sealed, and heated at 250°C and 600 psi for 12 hours. Upon completion of the reaction, chloroform was added and the reaction mixture was transferred to a separatory funnel for extraction. The extract was dried over MgSO4, concentrated, and the sample was purified by silica gel column chromatography to produce 5.1 g of compound 1-12. (Yield 49%, MS: [M+H] + =706)

[0782] Synthesis Example 1-13 [ka]

[0783] (4-chlorodibenzo[b,d]furan-1-yl)boronic acid (15 g, 60.9 mmol) and compound Trz12 (30 g, 63.9 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (25.2 g, 182.6 mmol) dissolved in 76 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 3 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 24.4 g of compound 1-13_P1. (Yield: 63%, MS: [M+H] + =636)

[0784] Compound 1-13_P1 (15 g, 23.6 mmol) and naphthalen-2-ylboronic acid (4.3 g, 24.8 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (9.8 g, 70.7 mmol) dissolved in 29 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 5 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 10.5 g of compound 1-13. (Yield 61%, MS: [M+H] + =728)

[0785] Synthesis Example 1-14 [ka]

[0786] (4-chlorodibenzo[b,d]furan-1-yl)boronic acid (15 g, 60.9 mmol) and compound Trz13 (22 g, 63.9 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (25.2 g, 182.6 mmol) dissolved in 76 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 3 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 22.3 g of compound 1-14_P1. (Yield 72%, MS: [M+H] + =510)

[0787] Compound 1-14_P1 (15 g, 29.4 mmol) and naphtho[2,3-b]benzofuran-4-ylboronic acid (8.1 g, 30.9 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (12.2 g, 88.2 mmol) dissolved in 37 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 4 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, added with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 14.2 g of compound 1-14. (Yield 70%, MS: [M+H] + =692)

[0788] Synthesis Example 1-15 [ka]

[0789] (4-chlorodibenzo[b,d]furan-1-yl)boronic acid (15 g, 60.9 mmol) and compound Trz14 (26.1 g, 63.9 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (25.2 g, 182.6 mmol) dissolved in 76 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 2 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 24.8 g of compound 1-15_P1. (Yield 71%, MS: [M+H] + =574)

[0790] Compound 1-15_P1 (15 g, 26.1 mmol) and dibenzo[b,d]furan-1-ylboronic acid (5.8 g, 27.4 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (10.8 g, 78.4 mmol) dissolved in 33 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 3 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 11.1 g of compound 1-15. (Yield 60%, MS: [M+H] + =706)

[0791] Synthesis Example 1-16 [ka]

[0792] Trifluoromethanesulfonic anhydride (45.1 g, 159.8 mmol) and deuterium oxide (16 g, 799.2 mmol) were added at 0°C and stirred for 5 hours to form a solution. 1-bromo-4-chlorodibenzo[b,d]furan (15 g, 53.3 mmol) was added to 120 mL of 1,2,4-trichlorobenzene and stirred. The prepared trifluoromethanesulfonic anhydride and deuterium oxide mixed solution was then slowly added dropwise to the 1-bromo-4-chlorodibenzo[b,d]furan and 1,2,4-trichlorobenzene mixed solution, heated to 140°C, and maintained at this temperature while stirring. After reacting for 7 hours, the mixture was cooled to room temperature and the organic and aqueous layers were separated. The organic layer was then neutralized with an aqueous potassium carbonate solution. After washing twice with water, the organic layer was separated, added to anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 5.6 g of compound Sub1-3-1 (yield 37%, MS: [M+H] + =284)

[0793] Compound Sub1-3-1 (15 g, 52.7 mmol) and bis(pinacolato)diboron (14.7 g, 58 mmol) were refluxed in 300 mL of 1,4-dioxane and stirred. Potassium acetate (7.8 g, 79.1 mmol) was then added and thoroughly stirred. Then, bis(dibenzylideneacetone)palladium(0) (0.9 g, 1.6 mmol) and tricyclohexylphosphine (0.9 g, 3.2 mmol) were added. The mixture was allowed to react for 6 hours, cooled to room temperature, and the organic layer was separated using chloroform and water. The organic layer was then distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 10.1 g of compound Sub1-3-2. (Yield: 58%, MS: [M+H] + =332)

[0794] Compound Sub1-3-2 (15 g, 45.2 mmol) and compound Trz15 (17.7 g, 47.5 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (18.8 g, 135.7 mmol) dissolved in 56 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After 2 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 15.4 g of compound 1-16_P1. (Yield: 63%, MS: [M+H] + =542)

[0795] Compound 1-16_P1 (15 g, 27.7 mmol) and (phenyl-d5)boronic acid (3.7 g, 29.1 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (11.5 g, 83 mmol) dissolved in 34 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 3 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 11.9 g of compound 1-16. (Yield 73%, MS: [M+H] + =589)

[0796] Synthesis Example 1-17 [ka]

[0797] (6-chlorodibenzo[b,d]furan-1-yl)boronic acid (15 g, 60.9 mmol) and compound Trz16 (23.5 g, 63.9 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (25.2 g, 182.6 mmol) dissolved in 76 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 2 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 23.4 g of compound 1-17_P1. (Yield 72%, MS: [M+H] + =534)

[0798] Compound 1-17_P1 (15 g, 28.1 mmol) and naphthalen-2-ylboronic acid (5.1 g, 29.5 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (11.6 g, 84.3 mmol) dissolved in 35 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 3 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.5 g of compound 1-17. (Yield 71%, MS: [M+H] + =626)

[0799] Synthesis Example 1-18 [ka]

[0800] (6-chlorodibenzo[b,d]furan-1-yl)boronic acid (15 g, 60.9 mmol) and compound Trz17 (29.7 g, 63.9 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (25.2 g, 182.6 mmol) dissolved in 76 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 24.6 g of compound 1-18_P1. (Yield: 69%, MS: [M+H] + =586)

[0801] Compound 1-18_P1 (15 g, 25.6 mmol) and naphthalen-2-ylboronic acid (4.6 g, 26.9 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (10.6 g, 76.8 mmol) dissolved in 32 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 2 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 10.9 g of compound 1-18. (Yield 63%, MS: [M+H] + =678)

[0802] Synthesis Example 1-19 [ka]

[0803] (6-chlorodibenzo[b,d]furan-1-yl)boronic acid (15 g, 60.9 mmol) and compound Trz18 (31.2 g, 63.9 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (25.2 g, 182.6 mmol) dissolved in 76 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 3 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 24.5 g of compound 1-19_P1. (Yield: 66%, MS: [M+H] + =610)

[0804] Compound 1-19_P1 (15 g, 24.6 mmol) and naphthalen-2-ylboronic acid (4.4 g, 25.8 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (10.2 g, 73.8 mmol) dissolved in 31 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 2 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 11.4 g of compound 1-19. (Yield: 66%, MS: [M+H] + =702)

[0805] Synthesis Example 1-20 [ka]

[0806] (6-chlorodibenzo[b,d]furan-1-yl)boronic acid (15 g, 60.9 mmol) and compound Trz19 (20.3 g, 63.9 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (25.2 g, 182.6 mmol) dissolved in 76 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 19.1 g of compound 1-20_P1. (Yield: 65%, MS: [M+H] + =484

[0807] Compound 1-20_P1 (15 g, 31 mmol) and phenanthren-9-ylboronic acid (7.2 g, 32.5 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (12.9 g, 93 mmol) dissolved in 39 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12 g of compound 1-20. (Yield: 62%, MS: [M+H] + =626)

[0808] Synthesis Example 1-21 [ka]

[0809] Trifluoromethanesulfonic anhydride (30.1 g, 106.6 mmol) and deuterium oxide (10.7 g, 532.8 mmol) were added to a solution at 0°C and stirred for 5 hours. 1-Bromo-6-chlorodibenzo[b,d]furan (15 g, 53.3 mmol) was added to 120 mL of 1,2,4-trichlorobenzene and stirred. The prepared trifluoromethanesulfonic anhydride and deuterium oxide mixture was then slowly added dropwise to the 1-bromo-6-chlorodibenzo[b,d]furan and 1,2,4-trichlorobenzene mixture, heated to 140°C, and maintained at this temperature while stirring. After 3 hours of reaction, the mixture was cooled to room temperature and the organic and aqueous layers were separated. The organic layer was then neutralized with an aqueous potassium carbonate solution. After washing twice with water, the organic layer was separated, added to anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 6.8 g of compound Sub2-1-1. (Yield: 45%, MS: [M+H] + =283)

[0810] Compound Sub2-1-1 (15 g, 52.9 mmol) and bis(pinacolato)diboron (14.8 g, 58.2 mmol) were refluxed in 300 mL of 1,4-dioxane and stirred. Potassium acetate (7.8 g, 79.4 mmol) was then added and thoroughly stirred. Then, bis(dibenzylideneacetone)palladium(0) (0.9 g, 1.6 mmol) and tricyclohexylphosphine (0.9 g, 3.2 mmol) were added. The mixture reacted for 6 hours, cooled to room temperature, and the organic layer was separated using chloroform and water. The organic layer was then distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 13.1 g of compound Sub2-1-2. (Yield: 75%, MS: [M+H]+ =331)

[0811] Compound Sub2-1-2 (15 g, 45.4 mmol) and compound Trz20 (22.6 g, 47.6 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (18.8 g, 136.1 mmol) dissolved in 56 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After 4 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 17.8 g of compound 1-21_P1. (Yield 61%, MS: [M+H] + =643)

[0812] Compound 1-21_P1 (15 g, 23.3 mmol) and (phenyl-d5)boronic acid (3.1 g, 24.5 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (9.7 g, 70 mmol) dissolved in 29 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 4 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 11.9 g of compound 1-21. (Yield 74%, MS: [M+H] + =690)

[0813] Synthesis Example 1-22 [ka]

[0814] Compound Sub2-1-2 (15 g, 45.4 mmol) and compound Trz21 (21.1 g, 47.6 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (18.8 g, 136.1 mmol) dissolved in 56 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After 4 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 18.6 g of compound 1-22_P1. (Yield: 67%, MS: [M+H] + =612)

[0815] Compound 1-22_P1 (15 g, 24.5 mmol) and (phenyl-d5)boronic acid (3.3 g, 25.7 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (10.2 g, 73.5 mmol) dissolved in 30 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 2 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 10 g of compound 1-22. (Yield: 62%, MS: [M+H] + =659)

[0816] Synthesis Example 1-23 [ka]

[0817] Trifluoromethanesulfonic anhydride (60.1 g, 213.1 mmol) and deuterium oxide (21.4 g, 1065.6 mmol) were added at 0°C and stirred for 5 hours to form a solution. 1-bromo-6-chlorodibenzo[b,d]furan (15 g, 53.3 mmol) was added to 120 mL of 1,2,4-trichlorobenzene and stirred. The prepared trifluoromethanesulfonic anhydride and deuterium oxide mixture was then slowly added dropwise to the 1-bromo-6-chlorodibenzo[b,d]furan and 1,2,4-trichlorobenzene mixture, heated to 140°C, and stirred. After 10 hours of reaction, the mixture was cooled to room temperature and the organic and aqueous layers were separated. The organic layer was then neutralized with an aqueous potassium carbonate solution. After washing twice with water, the organic layer was separated, added to anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 6.5 g of compound Sub2-2-1. (Yield: 43%, MS: [M+H] + =285)

[0818] Compound Sub2-2-1 (15 g, 52.5 mmol) and bis(pinacolato)diboron (14.7 g, 57.8 mmol) were refluxed in 300 mL of 1,4-dioxane and stirred. Potassium acetate (7.7 g, 78.8 mmol) was then added and thoroughly stirred. Then, bis(dibenzylideneacetone)palladium(0) (0.9 g, 1.6 mmol) and tricyclohexylphosphine (0.9 g, 3.2 mmol) were added. The mixture was allowed to react for 5 hours, cooled to room temperature, and the organic layer was separated using chloroform and water. The organic layer was then distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 13.1 g of compound Sub2-2-2. (Yield 75%, MS: [M+H]+ =333)

[0819] Compound Sub2-2-2 (15 g, 60.9 mmol) and compound Trz22 (36.1 g, 63.9 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (25.2 g, 182.6 mmol) dissolved in 76 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 3 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 28.9 g of compound 1-23_P1. (Yield: 69%, MS: [M+H] + =690)

[0820] Compound 1-23_P1 (15 g, 21.7 mmol) and phenylboronic acid (2.8 g, 22.8 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (9 g, 65.2 mmol) dissolved in 27 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 5 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 9.5 g of compound 1-23. (Yield 60%, MS: [M+H] + =732)

[0821] Synthesis Example 1-24 [ka]

[0822] Compound 1-18 (10 g, 14.8 mmol), PtO2 (1 g, 4.4 mmol), and 74 ml of DO were placed in a shaker tube, sealed, and heated at 250°C and 600 psi for 12 hours. Upon completion of the reaction, chloroform was added and the reaction mixture was transferred to a separatory funnel for extraction. The extract was dried over MgSO4, concentrated, and the sample was purified by silica gel column chromatography to produce 5.1 g of compound 1-24. (Yield 49%, MS: [M+H] + =706)

[0823] Synthesis Example 1-25 [ka]

[0824] (6-chlorodibenzo[b,d]furan-1-yl)boronic acid (15 g, 60.9 mmol) and compound Trz23 (25.2 g, 63.9 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (25.2 g, 182.6 mmol) dissolved in 76 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 3 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 20.7 g of compound 1-25_P1. (Yield: 63%, MS: [M+H] + =540)

[0825] Compound 1-25_P1 (15 g, 27.8 mmol) and dibenzo[b,d]furan-1-ylboronic acid (6.2 g, 29.2 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (11.5 g, 83.3 mmol) dissolved in 35 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 5 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, and stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 11.4 g of compound 1-25_P2. (Yield: 61%, MS: [M+H] + =672)

[0826] Compound 1-25_P2 (10 g, 14.9 mmol), PtO2 (1 g, 4.5 mmol), and 74 ml of DO were placed in a shaker tube, sealed, and heated at 250°C and 600 psi for 12 hours. Upon completion of the reaction, chloroform was added and the reaction mixture was transferred to a separatory funnel for extraction. The extract was dried over MgSO4, concentrated, and the sample was purified by silica gel column chromatography to produce 3.7 g of compound 1-25. (Yield 36%, MS: [M+H] + =695)

[0827] Synthesis Example 1-26 [ka]

[0828] (7-chlorodibenzo[b,d]furan-1-yl)boronic acid (15 g, 60.9 mmol) and compound Trz19 (20.3 g, 63.9 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (25.2 g, 182.6 mmol) dissolved in 76 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 4 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 17.6 g of compound 1-26_P1. (Yield: 60%, MS: [M+H] + =484)

[0829] Compound 1-26_P1 (15 g, 31 mmol) and naphthalen-2-ylboronic acid (5.6 g, 32.5 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (12.9 g, 93 mmol) dissolved in 39 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 13 g of compound 1-26. (Yield 73%, MS: [M+H] + =576)

[0830] Synthesis Example 1-27 [ka]

[0831] (7-chlorodibenzo[b,d]furan-1-yl)boronic acid (15 g, 60.9 mmol) and compound Trz24 (22.9 g, 63.9 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (25.2 g, 182.6 mmol) dissolved in 76 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 20.4 g of compound 1-27_P1. (Yield: 64%, MS: [M+H] + =524)

[0832] Compound 1-27_P1 (15 g, 28.6 mmol) and naphthalen-2-ylboronic acid (5.2 g, 30.1 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (11.9 g, 85.9 mmol) dissolved in 36 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 3 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 10.9 g of compound 1-27. (Yield: 62%, MS: [M+H] + =616)

[0833] Synthesis Example 1-28 [ka]

[0834] (7-chlorodibenzo[b,d]furan-1-yl)boronic acid (15 g, 60.9 mmol) and compound Trz25 (22.9 g, 63.9 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (25.2 g, 182.6 mmol) dissolved in 76 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 2 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 22.6 g of compound 1-28_P1. (Yield 71%, MS: [M+H] + =524)

[0835] Compound 1-28_P1 (15 g, 28.6 mmol) and phenanthren-3-ylboronic acid (6.7 g, 30.1 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (11.9 g, 85.9 mmol) dissolved in 36 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 3 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.9 g of compound 1-28. (Yield 68%, MS: [M+H] + =666)

[0836] Synthesis Example 1-29 [ka]

[0837] (7-chlorodibenzo[b,d]furan-1-yl)boronic acid (15 g, 60.9 mmol) and compound Trz26 (25.2 g, 63.9 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (25.2 g, 182.6 mmol) dissolved in 76 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 2 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 21.1 g of compound 1-29_P1. (Yield: 62%, MS: [M+H] + =560)

[0838] Compound 1-29_P1 (15 g, 26.8 mmol) and dibenzo[b,d]thiophen-4-ylboronic acid (6.4 g, 28.1 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (11.1 g, 80.3 mmol) dissolved in 33 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 3 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.3 g of compound 1-29. (Yield 65%, MS: [M+H] + =708)

[0839] Synthesis Example 1-30 [ka]

[0840] (7-chlorodibenzo[b,d]furan-1-yl)boronic acid (15 g, 60.9 mmol) and compound Trz27 (38.6 g, 63.9 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (25.2 g, 182.6 mmol) dissolved in 76 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 29.1 g of compound 1-30_P1. (Yield: 66%, MS: [M+H] + =726)

[0841] Compound 1-30_P1 (15 g, 20.7 mmol) and naphthalen-2-ylboronic acid (3.7 g, 21.7 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (8.6 g, 62 mmol) dissolved in 26 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 3 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 10.6 g of compound 1-30. (Yield 63%, MS: [M+H] + =818)

[0842] Synthesis Example 1-31 [ka]

[0843] Trifluoromethanesulfonic anhydride (30.1 g, 106.6 mmol) and deuterium oxide (10.7 g, 532.8 mmol) were added to a solution at 0°C and stirred for 5 hours. 1-Bromo-7-chlorodibenzo[b,d]furan (15 g, 53.3 mmol) was added to 120 mL of 1,2,4-trichlorobenzene and stirred. The prepared trifluoromethanesulfonic anhydride and deuterium oxide mixture was then slowly added dropwise to the 1-bromo-7-chlorodibenzo[b,d]furan and 1,2,4-trichlorobenzene mixture, heated to 140°C, and maintained at this temperature while stirring. After reacting for 3 hours, the mixture was cooled to room temperature and the organic and aqueous layers were separated. The organic layer was then neutralized with an aqueous potassium carbonate solution. After washing twice with water, the organic layer was separated, added to anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 6 g of compound Sub3-1-1. (Yield: 40%, MS: [M+H] + =283)

[0844] Compound Sub3-1-1 (15 g, 52.9 mmol) and bis(pinacolato)diboron (14.8 g, 58.2 mmol) were refluxed in 300 mL of 1,4-dioxane and stirred. Potassium acetate (7.8 g, 79.4 mmol) was then added and thoroughly stirred. Then, bis(dibenzylideneacetone)palladium(0) (0.9 g, 1.6 mmol) and tricyclohexylphosphine (0.9 g, 3.2 mmol) were added. The mixture reacted for 4 hours, cooled to room temperature, and the organic layer was separated using chloroform and water. The organic layer was then distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 11.4 g of compound Sub3-1-2. (Yield: 65%, MS: [M+H] + =331)

[0845] Compound Sub3-1-2 (15 g, 45.4 mmol) and compound Trz28 (28.6 g, 47.6 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (18.8 g, 136.1 mmol) dissolved in 56 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After 2 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 20.3 g of compound 1-31_P1. (Yield: 62%, MS: [M+H] + =723)

[0846] Compound 1-31_P1 (15 g, 20.7 mmol) and phenanthren-3-ylboronic acid (4.8 g, 21.8 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (8.6 g, 62.2 mmol) dissolved in 26 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 2 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 11.5 g of compound 1-31. (Yield 64%, MS: [M+H] + =866)

[0847] Synthesis Example 1-32 [ka]

[0848] Trifluoromethanesulfonic anhydride (60.1 g, 213.1 mmol) and deuterium oxide (21.4 g, 1065.6 mmol) were added to a solution at 0°C and stirred for 5 hours. 1-Bromo-7-chlorodibenzo[b,d]furan (15 g, 53.3 mmol) was added to 120 mL of 1,2,4-trichlorobenzene and stirred. The prepared trifluoromethanesulfonic anhydride and deuterium oxide mixture was then slowly added dropwise to the 1-bromo-7-chlorodibenzo[b,d]furan and 1,2,4-trichlorobenzene mixture, heated to 140°C, and maintained at this temperature while stirring. After 10 hours of reaction, the mixture was cooled to room temperature and the organic and aqueous layers were separated. The organic layer was then neutralized with an aqueous potassium carbonate solution. After washing twice with water, the organic layer was separated, added to anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 6.7 g of compound Sub3-2-1 (yield 44%, MS: [M+H] + =285)

[0849] Compound Sub3-2-1 (15 g, 52.5 mmol) and bis(pinacolato)diboron (14.7 g, 57.8 mmol) were refluxed in 300 mL of 1,4-dioxane and stirred. Potassium acetate (7.7 g, 78.8 mmol) was then added and thoroughly stirred. Then, bis(dibenzylideneacetone)palladium(0) (0.9 g, 1.6 mmol) and tricyclohexylphosphine (0.9 g, 3.2 mmol) were added. The mixture reacted for 6 hours, cooled to room temperature, and the organic layer was separated using chloroform and water. The organic layer was then distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 11.7 g of compound Sub3-2-2. (Yield: 67%, MS: [M+H]+ =333)

[0850] Compound Sub3-2-2 (15 g, 45.1 mmol) and compound Trz29 (18.7 g, 47.4 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (18.7 g, 135.3 mmol) dissolved in 56 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After 2 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 18 g of compound 1-32_P1. (Yield 71%, MS: [M+H] + =564)

[0851] Compound 1-32_P1 (15 g, 26.6 mmol) and (phenyl-d5)boronic acid (3.5 g, 27.9 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (11 g, 79.8 mmol) dissolved in 33 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 3 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 11.4 g of compound 1-32. (Yield 70%, MS: [M+H] + =611)

[0852] Synthesis Example 1-33 [ka]

[0853] Compound Sub3-2-2 (15 g, 45.1 mmol) and compound Trz30 (24.8 g, 47.4 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (18.7 g, 135.3 mmol) dissolved in 56 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After 2 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 18.4 g of compound 1-33_P1. (Yield: 63%, MS: [M+H] + =650)

[0854] Compound 1-33_P1 (15 g, 23.1 mmol) and phenylboronic acid (3 g, 24.2 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (9.6 g, 69.2 mmol) dissolved in 29 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 2 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 11.5 g of compound 1-33. (Yield 72%, MS: [M+H] + =692)

[0855] Synthesis Example 1-34 [ka]

[0856] Compound 1-26 (10 g, 17.4 mmol), PtO2 (1.2 g, 5.2 mmol), and 87 ml of DO were placed in a shaker tube, sealed, and heated at 250°C and 600 psi for 12 hours. Upon completion of the reaction, chloroform was added and the reaction mixture was transferred to a separatory funnel for extraction. The extract was dried over MgSO4, concentrated, and the sample was purified by silica gel column chromatography to produce 3.9 g of compound 1-34. (Yield 38%, MS: [M+H] + =598)

[0857] Synthesis Example 1-35 [ka]

[0858] (7-chlorodibenzo[b,d]furan-1-yl)boronic acid (15 g, 60.9 mmol) and compound Trz29 (25.2 g, 63.9 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (25.2 g, 182.6 mmol) dissolved in 76 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 2 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 23.8 g of compound 1-35_P1. (Yield 70%, MS: [M+H] + =560)

[0859] Compound 1-35_P1 (15 g, 26.8 mmol) and phenylboronic acid (3.4 g, 28.1 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (11.1 g, 80.3 mmol) dissolved in 33 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 5 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 11.3 g of compound 1-35_P2. (Yield: 70%, MS: [M+H] + =602)

[0860] Compound 1-35_P2 (10 g, 16.6 mmol), PtO2 (1.1 g, 5 mmol), and 83 ml of DO were placed in a shaker tube, sealed, and heated at 250°C and 600 psi for 12 hours. Upon completion of the reaction, chloroform was added and the reaction mixture was transferred to a separatory funnel for extraction. The extract was dried over MgSO4, concentrated, and the sample was purified by silica gel column chromatography to produce 3.7 g of compound 1-35. (Yield 36%, MS: [M+H] + =626)

[0861] Synthesis Example 1-36 [ka]

[0862] Compound 1-27 (10 g, 16.2 mmol), PtO2 (1.1 g, 4.9 mmol), and 81 ml of DO were placed in a shaker tube, sealed, and heated at 250°C and 600 psi for 12 hours. Upon completion of the reaction, chloroform was added and the reaction mixture was transferred to a separatory funnel for extraction. The extract was dried over MgSO4, concentrated, and the sample was purified by silica gel column chromatography to produce 3.9 g of compound 1-36. (Yield 38%, MS: [M+H] + =639)

[0863] Synthesis Example 1-37 [ka]

[0864] (8-chlorodibenzo[b,d]furan-1-yl)boronic acid (15 g, 60.9 mmol) and compound Trz31 (26.8 g, 63.9 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (25.2 g, 182.6 mmol) dissolved in 76 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 26.7 g of compound 1-37_P1. (Yield 75%, MS: [M+H] + =586)

[0865] Compound 1-37_P1 (15 g, 25.6 mmol) and naphthalen-2-ylboronic acid (4.6 g, 26.9 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (10.6 g, 76.8 mmol) dissolved in 32 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 3 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.7 g of compound 1-37. (Yield 73%, MS: [M+H] + =678)

[0866] Synthesis Example 1-38 [ka]

[0867] (8-chlorodibenzo[b,d]furan-1-yl)boronic acid (15 g, 60.9 mmol) and compound Trz5 (17.1 g, 63.9 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (25.2 g, 182.6 mmol) dissolved in 76 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 2 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 16.3 g of compound 1-38_P1. (Yield: 62%, MS: [M+ H]+ =434)

[0868] Compound 1-38_P1 (15 g, 34.6 mmol) and triphenylen-2-ylboronic acid (9.9 g, 36.3 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (14.3 g, 103.7 mmol) dissolved in 43 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 4 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 14.7 g of compound 1-38. (Yield: 68%, MS: [M+H] + =626)

[0869] Synthesis Example 1-39 [ka]

[0870] (8-chlorodibenzo[b,d]furan-1-yl)boronic acid (15 g, 60.9 mmol) and compound Trz32 (32.9 g, 63.9 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (25.2 g, 182.6 mmol) dissolved in 76 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 2 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 27.8 g of compound 1-39_P1. (Yield 72%, MS: [M+H] + =636)

[0871] Compound 1-39_P1 (15 g, 23.6 mmol) and dibenzo[b,d]furan-4-ylboronic acid (5.2 g, 24.8 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (9.8 g, 70.7 mmol) dissolved in 29 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 5 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 11.6 g of compound 1-39. (Yield: 64%, MS: [M+H] + =769)

[0872] Synthesis Example 1-40 [ka]

[0873] Trifluoromethanesulfonic anhydride (60.1 g, 213.1 mmol) and deuterium oxide (21.4 g, 1065.6 mmol) were added to a solution at 0°C and stirred for 5 hours. 1-Bromo-8-chlorodibenzo[b,d]furan (15 g, 53.3 mmol) was added to 120 mL of 1,2,4-trichlorobenzene and stirred. The prepared trifluoromethanesulfonic anhydride and deuterium oxide mixture was then slowly added dropwise to the 1-bromo-8-chlorodibenzo[b,d]furan and 1,2,4-trichlorobenzene mixture, heated to 140°C, and maintained at this temperature while stirring. After 10 hours of reaction, the mixture was cooled to room temperature and the organic and aqueous layers were separated. The organic layer was then neutralized with an aqueous potassium carbonate solution. After washing twice with water, the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 6.4 g of compound Sub4-1-1 (yield 42%, MS: [M+H] + =285)

[0874] Compound Sub4-1-1 (15 g, 52.5 mmol) and bis(pinacolato)diboron (14.7 g, 57.8 mmol) were refluxed in 300 mL of 1,4-dioxane and stirred. Potassium acetate (7.7 g, 78.8 mmol) was then added and thoroughly stirred. Then, bis(dibenzylideneacetone)palladium(0) (0.9 g, 1.6 mmol) and tricyclohexylphosphine (0.9 g, 3.2 mmol) were added. The mixture was allowed to react for 6 hours, cooled to room temperature, and the organic layer was separated using chloroform and water. The organic layer was then distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12 g of compound Sub4-1-2. (Yield: 69%, MS: [M+H]+ =333)

[0875] Compound Sub4-1-2 (15 g, 45.1 mmol) and compound Trz33 (17.8 g, 47.4 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (18.7 g, 135.3 mmol) dissolved in 56 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After 5 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 16 g of compound 1-40_P1. (Yield 65%, MS: [M+H] + =546)

[0876] Compound 1-40_P1 (15 g, 27.5 mmol) and dibenzo[b,d]furan-4-ylboronic acid (6.1 g, 28.8 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (11.4 g, 82.4 mmol) dissolved in 34 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 2 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 11.5 g of compound 1-40. (Yield: 62%, MS: [M+H] + =678)

[0877] Synthesis Example 1-41 [ka]

[0878] Compound Sub4-1-2 (15 g, 45.1 mmol) and compound Trz34 (20.3 g, 47.4 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (18.7 g, 135.3 mmol) dissolved in 56 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After 4 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 19.4 g of compound 1-41_P1. (Yield 72%, MS: [M+H] + =599

[0879] Compound 1-41_P1 (15 g, 25 mmol) and phenylboronic acid (3.2 g, 26.3 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (10.4 g, 75.1 mmol) dissolved in 31 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 2 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 9.8 g of compound 1-41. (Yield 61%, MS: [M+H] + =641)

[0880] Synthesis Example 1-42 [ka]

[0881] Compound Sub4-1-2 (15 g, 45.1 mmol) and compound Trz35 (21.3 g, 47.4 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (18.7 g, 135.3 mmol) dissolved in 56 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After 4 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 17 g of compound 1-42_P1. (Yield 61%, MS: [M+H] + =619)

[0882] Compound 1-42_P1 (15 g, 24.2 mmol) and (phenyl-d5)boronic acid (3.2 g, 25.4 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (10 g, 72.7 mmol) dissolved in 30 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 3 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 11.1 g of compound 1-42. (Yield 69%, MS: [M+H] + =666)

[0883] Synthesis Example 1-43 [ka] Compound 1-38 (10 g, 16 mmol), PtO2 (1.1 g, 4.8 mmol), and 80 ml of DO were placed in a shaker tube, sealed, and heated at 250°C and 600 psi for 12 hours. Upon completion of the reaction, chloroform was added and the reaction mixture was transferred to a separatory funnel for extraction. The extract was dried over MgSO4, concentrated, and the sample was purified by silica gel column chromatography to produce 3.5 g of 1-43. (Yield 34%, MS: [M+H] + =649)

[0884] Synthesis Example 1-44 [ka]

[0885] Trifluoromethanesulfonic anhydride (24 g, 85 mmol) and deuterium oxide (8.5 g, 424.9 mmol) were added to 0°C and stirred for 5 hours to form a solution. 1-Bromodibenzo[b,d]furan (15 g, 60.7 mmol) was added to 120 mL of 1,2,4-trichlorobenzene and stirred. The prepared trifluoromethanesulfonic anhydride and deuterium oxide mixed solution was then slowly added dropwise to the 1-bromodibenzo[b,d]furan and 1,2,4-trichlorobenzene mixed solution, heated to 140°C, and maintained at this temperature while stirring. After 5 hours of reaction, the mixture was cooled to room temperature and the organic and aqueous layers were separated. The organic layer was then neutralized with an aqueous potassium carbonate solution. After washing twice with water, the organic layer was separated, added to anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 5.7 g of compound Sub5-1-1. (Yield: 38%, MS: [M+H] + =248)

[0886] Compound Sub5-1-1 (15 g, 60.5 mmol) and bis(pinacolato)diboron (16.9 g, 66.5 mmol) were refluxed in 300 mL of 1,4-dioxane and stirred. Potassium acetate (8.9 g, 90.7 mmol) was then added and thoroughly stirred. Then, bis(dibenzylideneacetone)palladium(0) (1 g, 1.8 mmol) and tricyclohexylphosphine (1 g, 3.6 mmol) were added. The mixture was allowed to react for 6 hours, cooled to room temperature, and the organic layer was separated using chloroform and water. The organic layer was then distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 13.4 g of compound Sub5-1-2. (Yield 75%, MS: [M+H] + =296)

[0887] Compound Sub5-1-2 (15 g, 50.8 mmol) and compound Trz36 (25.8 g, 53.4 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (21.1 g, 152.5 mmol) dissolved in 63 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After 5 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 18.9 g of compound 1-44. (Yield 72%, MS: [M+H] + =518)

[0888] Synthesis Example 1-45 [ka]

[0889] Trifluoromethanesulfonic anhydride (48 g, 170 mmol) and deuterium oxide (17 g, 849.9 mmol) were added at 0°C and stirred for 5 hours to form a solution. 1-Bromodibenzo[b,d]furan (15 g, 60.7 mmol) was added to 120 mL of 1,2,4-trichlorobenzene and stirred. The prepared trifluoromethanesulfonic anhydride and deuterium oxide mixed solution was then slowly added dropwise to the 1-bromodibenzo[b,d]furan and 1,2,4-trichlorobenzene mixed solution, heated to 140°C, and maintained while stirring. After 8 hours of reaction, the mixture was cooled to room temperature and the organic and aqueous layers were separated. The organic layer was then neutralized with an aqueous potassium carbonate solution. After washing twice with water, the organic layer was separated, added to anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 6 g of compound Sub5-2-1. (Yield: 40%, MS: [M+H] + =249)

[0890] Compound Sub5-2-1 (15 g, 60.2 mmol) and bis(pinacolato)diboron (16.8 g, 66.2 mmol) were refluxed in 300 mL of 1,4-dioxane and stirred. Potassium acetate (8.9 g, 90.3 mmol) was then added and thoroughly stirred. Then, bis(dibenzylideneacetone)palladium(0) (1 g, 1.8 mmol) and tricyclohexylphosphine (1 g, 3.6 mmol) were added. The mixture was allowed to react for 4 hours, cooled to room temperature, and the organic layer was separated using chloroform and water. The organic layer was then distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.5 g of compound Sub5-2-2. (Yield: 70%, MS: [M+H] + =297)

[0891] Compound Sub5-2-2 (15 g, 50.6 mmol) and compound Trz37 (23.9 g, 53.2 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (21 g, 151.9 mmol) dissolved in 63 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After 2 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 19.5 g of compound 1-45. (Yield 66%, MS: [M+H] + =583)

[0892] Synthesis Example 1-46 [ka]

[0893] Compound Sub5-2-2 (15 g, 50.6 mmol) and compound Trz38 (28 g, 53.2 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (21 g, 151.9 mmol) dissolved in 63 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After 5 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 21.4 g of compound 1-46. (Yield: 64%, MS: [M+H] + =660)

[0894] Synthesis Example 1-47 [ka]

[0895] Compound Sub5-2-2 (15 g, 50.6 mmol) and compound Trz39 (21.9 g, 53.2 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (21 g, 151.9 mmol) dissolved in 63 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After 5 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 19.1 g of compound 1-47. (Yield: 69%, MS: [M+H] + =546)

[0896] Synthesis Example 1-48 [ka]

[0897] Compound Sub5-2-2 (15 g, 50.6 mmol) and compound Trz40 (31.7 g, 53.2 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (21 g, 151.9 mmol) dissolved in 63 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After 2 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 23.9 g of compound 1-48. (Yield 69%, MS: [M+H] + =685)

[0898] Synthesis Example 1-49 [ka]

[0899] Compound Sub5-2-2 (15 g, 50.6 mmol) and compound Trz41 (25.4 g, 53.2 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (21 g, 151.9 mmol) dissolved in 63 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After 4 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 21.5 g of compound 1-49. (Yield 75%, MS: [M+H] + =568)

[0900] Synthesis Example 1-50 [ka]

[0901] Trifluoromethanesulfonic anhydride (71.9 g, 255 mmol) and deuterium oxide (25.5 g, 1274.8 mmol) were added at 0°C and stirred for 5 hours to form a solution. 1-Bromodibenzo[b,d]furan (15 g, 60.7 mmol) was added to 120 mL of 1,2,4-trichlorobenzene and stirred. The prepared trifluoromethanesulfonic anhydride and deuterium oxide mixed solution was then slowly added dropwise to the 1-bromodibenzo[b,d]furan and 1,2,4-trichlorobenzene mixed solution, heated to 140°C, and maintained at this temperature while stirring. After 14 hours of reaction, the mixture was cooled to room temperature and the organic and aqueous layers were separated. The organic layer was then neutralized with an aqueous potassium carbonate solution. After washing twice with water, the organic layer was separated, added to anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 6.3 g of compound Sub5-3-1 (yield 42%, MS: [M+H] + =250)

[0902] Compound Sub5-3-1 (15 g, 60 mmol) and bis(pinacolato)diboron (16.8 g, 66 mmol) were refluxed in 300 mL of 1,4-dioxane and stirred. Potassium acetate (8.8 g, 90 mmol) was then added and thoroughly stirred. Then, bis(dibenzylideneacetone)palladium(0) (1 g, 1.8 mmol) and tricyclohexylphosphine (1 g, 3.6 mmol) were added. The mixture was allowed to react for 6 hours, cooled to room temperature, and the organic layer was separated using chloroform and water. The organic layer was then distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 11.4 g of compound Sub5-3-2. (Yield: 64%, MS: [M+H] + =298)

[0903] Compound Sub5-3-2 (15 g, 50.5 mmol) and compound Trz42 (25.2 g, 53 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (20.9 g, 151.4 mmol) dissolved in 63 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After 2 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 20.3 g of compound 1-50. (Yield 66%, MS: [M+H] + =610)

[0904] Synthesis Example 1-51 [ka]

[0905] Compound Sub5-3-2 (15 g, 50.5 mmol) and compound Trz43 (23.5 g, 53 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (20.9 g, 151.4 mmol) dissolved in 63 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After 3 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 18.6 g of compound 1-51. (Yield 69%, MS: [M+H] + =534)

[0906] Synthesis Example 1-52 [ka]

[0907] Compound Sub5-3-2 (15 g, 50.5 mmol) and compound Trz44 (22.8 g, 53 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (20.9 g, 151.4 mmol) dissolved in 63 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After 4 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 21.1 g of compound 1-52. (Yield 74%, MS: [M+H] + =565)

[0908] Synthesis Example 1-53 [ka]

[0909] Trifluoromethanesulfonic anhydride (95.9 g, 340 mmol) and deuterium oxide (34 g, 1699.8 mmol) were added at 0°C and stirred for 5 hours to form a solution. 1-Bromodibenzo[b,d]furan (15 g, 60.7 mmol) was added to 120 mL of 1,2,4-trichlorobenzene and stirred. The prepared trifluoromethanesulfonic anhydride and deuterium oxide mixed solution was then slowly added dropwise to the 1-bromodibenzo[b,d]furan and 1,2,4-trichlorobenzene mixed solution, heated to 140°C, and maintained at this temperature while stirring. After reacting for 20 hours, the mixture was cooled to room temperature and the organic and aqueous layers were separated. The organic layer was then neutralized with an aqueous potassium carbonate solution. After washing twice with water, the organic layer was separated, added to anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 5.6 g of compound Sub5-4-1 (yield 37%, MS: [M+H] + =251)

[0910] Compound Sub5-4-1 (15 g, 59.7 mmol) and bis(pinacolato)diboron (16.7 g, 65.7 mmol) were refluxed in 300 mL of 1,4-dioxane and stirred. Potassium acetate (8.8 g, 89.6 mmol) was then added and thoroughly stirred. Then, bis(dibenzylideneacetone)palladium(0) (1 g, 1.8 mmol) and tricyclohexylphosphine (1 g, 3.6 mmol) were added. The mixture was allowed to react for 5 hours, cooled to room temperature, and the organic layer was separated using chloroform and water. The organic layer was then distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.5 g of compound Sub5-4-2. (Yield: 70%, MS: [M+H] + =299)

[0911] Compound Sub5-4-2 (15 g, 50.3 mmol) and compound Trz45 (28.1 g, 52.8 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (20.9 g, 150.9 mmol) dissolved in 63 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After 4 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 23.8 g of compound 1-53. (Yield 71%, MS: [M+H] + =668)

[0912] Synthesis Example 1-54 [ka]

[0913] Trifluoromethanesulfonic anhydride (119.9 g, 424.9 mmol) and deuterium oxide (42.6 g, 2124.7 mmol) were added to a solution at 0°C and stirred for 5 hours. 1-Bromodibenzo[b,d]furan (15 g, 60.7 mmol) was added to 120 mL of 1,2,4-trichlorobenzene and stirred. The prepared trifluoromethanesulfonic anhydride and deuterium oxide mixed solution was then slowly added dropwise to the 1-bromodibenzo[b,d]furan and 1,2,4-trichlorobenzene mixed solution, heated to 140°C, and maintained while stirring. After 24 hours of reaction, the mixture was cooled to room temperature and the organic and aqueous layers were separated. The organic layer was then neutralized with an aqueous potassium carbonate solution. After washing twice with water, the organic layer was separated, added to anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 5.9 g of compound Sub5-5-1 (yield 39%, MS: [M+H] + =252)

[0914] Compound Sub5-5-1 (15 g, 59.5 mmol) and bis(pinacolato)diboron (16.6 g, 65.4 mmol) were refluxed in 300 mL of 1,4-dioxane and stirred. Potassium acetate (8.8 g, 89.2 mmol) was then added and thoroughly stirred. Then, bis(dibenzylideneacetone)palladium(0) (1 g, 1.8 mmol) and tricyclohexylphosphine (1 g, 3.6 mmol) were added. The mixture was allowed to react for 4 hours, cooled to room temperature, and the organic layer was separated using chloroform and water. The organic layer was then distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 11.2 g of compound Sub5-5-2. (Yield: 63%, MS: [M+H] + =300)

[0915] Compound Sub5-5-2 (15 g, 50.1 mmol) and compound Trz46 (27.6 g, 52.6 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (20.8 g, 150.4 mmol) dissolved in 62 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After 5 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 21.2 g of compound 1-54. (Yield 73%, MS: [M+H] + =581)

[0916] Synthesis Example 1-55 [ka]

[0917] Compound Sub5-5-2 (15 g, 50.1 mmol) and compound Trz47 (27.6 g, 52.6 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (20.8 g, 150.4 mmol) dissolved in 62 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After 4 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, and stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 24.9 g of compound 1-55. (Yield 75%, MS: [M+H] + =662)

[0918] Synthesis Example 1-56 [ka]

[0919] Compound Sub5-5-2 (15 g, 50.1 mmol) and compound Trz22 (29.7 g, 52.6 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (20.8 g, 150.4 mmol) dissolved in 62 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After 4 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 23.4 g of compound 1-56. (Yield 71%, MS: [M+H] + =657)

[0920] Synthesis Example 1-57 [ka]

[0921] Compound Sub5-5-2 (15 g, 50.1 mmol) and compound Trz48 (27.3 g, 52.6 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (20.8 g, 150.4 mmol) dissolved in 62 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After 4 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 19 g of compound 1-57. (Yield 62%, MS: [M+H] + =612)

[0922] Synthesis Example 1-58 [ka]

[0923] Compound Sub5-5-2 (15 g, 50.1 mmol) and compound Trz49 (27.1 g, 52.6 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (20.8 g, 150.4 mmol) dissolved in 62 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After 5 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 19.5 g of compound 1-58. (Yield: 64%, MS: [M+H] + =607)

[0924] Synthesis Example 1-59 [ka]

[0925] Trifluoromethanesulfonic anhydride (167.8 g, 594.9 mmol) and deuterium oxide (59.6 g, 2974.6 mmol) were added to 0°C and stirred for 5 hours to form a solution. 1-Bromodibenzo[b,d]furan (15 g, 60.7 mmol) was added to 120 mL of 1,2,4-trichlorobenzene and stirred. The prepared trifluoromethanesulfonic anhydride and deuterium oxide mixed solution was then slowly added dropwise to the 1-bromodibenzo[b,d]furan and 1,2,4-trichlorobenzene mixed solution, heated to 140°C, and maintained while stirring. After 36 hours of reaction, the mixture was cooled to room temperature and the organic and aqueous layers were separated. The organic layer was then neutralized with an aqueous potassium carbonate solution. After washing twice with water, the organic layer was separated, added to anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 6.1 g of compound Sub5-6-1. (Yield: 40%, MS: [M+H] + =254)

[0926] Compound Sub5-6-1 (15 g, 59 mmol) and bis(pinacolato)diboron (16.5 g, 64.9 mmol) were refluxed in 300 mL of 1,4-dioxane and stirred. Potassium acetate (8.7 g, 88.5 mmol) was then added and thoroughly stirred. Then, bis(dibenzylideneacetone)palladium(0) (1 g, 1.8 mmol) and tricyclohexylphosphine (1 g, 3.5 mmol) were added. The mixture was allowed to react for 4 hours, cooled to room temperature, and the organic layer was separated using chloroform and water. The organic layer was then distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 11.6 g of compound Sub5-6-2. (Yield: 65%, MS: [M+H] + =302)

[0927] Compound Sub5-6-2 (15 g, 50 mmol) and compound Trz50 (24.2 g, 52.5 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (20.7 g, 149.9 mmol) dissolved in 62 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After 3 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 22.5 g of compound 1-59. (Yield 75%, MS: [M+H] + =601)

[0928] Synthesis Example 1-60 [ka]

[0929] Compound Sub5-6-2 (15 g, 50 mmol) and compound Trz51 (24.1 g, 52.5 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (20.7 g, 149.9 mmol) dissolved in 62 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After 5 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 22.1 g of compound 1-60. (Yield 74%, MS: [M+H] + =599)

[0930] Synthesis Example 1-61 [ka]

[0931] Compound Sub5-6-2 (15 g, 50 mmol) and compound Trz52 (25.3 g, 52.5 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (20.7 g, 149.9 mmol) dissolved in 62 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After 5 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 21.6 g of compound 1-61. (Yield 75%, MS: [M+H] + =577)

[0932] Synthesis Example 1-62 [ka]

[0933] Compound Sub5-6-2 (15 g, 50 mmol) and compound Trz53 (32 g, 52.5 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (20.7 g, 149.9 mmol) dissolved in 62 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After 3 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 26 g of compound 1-62. (Yield 74%, MS: [M+H] + =704)

[0934] Synthesis Example 1-63 [ka]

[0935] Compound Sub5-6-2 (15 g, 50 mmol) and compound Trz54 (27.3 g, 52.5 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (20.7 g, 149.9 mmol) dissolved in 62 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After 5 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 18.4 g of compound 1-63. (Yield: 60%, MS: [M+H] + =615)

[0936] Synthesis Example 1-64 [ka]

[0937] Dibenzo[b,d]furan-1-ylboronic acid (15 g, 70.8 mmol) and compound Trz554 (5.7 g, 74.3 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (29.3 g, 212.3 mmol) dissolved in 88 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.7 mmol) was added. After 5 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 32.2 g of compound 1-64_P1. (Yield 65%, MS: [M+H] + =702)

[0938] Compound 1-64_P1 (10 g, 14.2 mmol), PtO2 (1 g, 4.3 mmol), and 71 ml of DO were placed in a shaker tube, sealed, and heated at 250°C and 600 psi for 12 hours. Upon completion of the reaction, chloroform was added and the reaction mixture was transferred to a separatory funnel for extraction. The extract was dried over MgSO4, concentrated, and the sample was purified by silica gel column chromatography to produce 4 g of compound 1-64. (Yield 39%, MS: [M+H] + =727)

[0939] Synthesis Example 1-65 [ka] Dibenzo[b,d]furan-1-ylboronic acid (15 g, 70.8 mmol) and compound Trz56 (33 g, 74.3 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (29.3 g, 212.3 mmol) dissolved in 88 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.7 mmol) was added. After 5 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 29.7 g of compound 1-65_P1. (Yield 73%, MS: [M+H] + =576)

[0940] Compound 1-65_P1 (10 g, 17.4 mmol), PtO2 (1.2 g, 5.2 mmol), and 87 ml of DO were placed in a shaker tube, sealed, and heated at 250°C and 600 psi for 12 hours. Upon completion of the reaction, chloroform was added and the reaction mixture was transferred to a separatory funnel for extraction. The extract was dried over MgSO4, concentrated, and the sample was purified by silica gel column chromatography to produce 5.1 g of compound 1-65. (Yield 49%, MS: [M+H] + =599)

[0941] Synthesis Example 1-66 [ka]

[0942] Dibenzo[b,d]furan-1-ylboronic acid (15 g, 70.8 mmol) and compound Trz46 (33 g, 74.3 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (29.3 g, 212.3 mmol) dissolved in 88 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.7 mmol) was added. After 3 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 24.8 g of compound 1-66_P1. (Yield: 61%, MS: [M+H] + =576)

[0943] Compound 1-66_P1 (10 g, 17.4 mmol), PtO2 (1.2 g, 5.2 mmol), and 87 ml of DO were placed in a shaker tube, sealed, and heated at 250°C and 600 psi for 12 hours. Upon completion of the reaction, chloroform was added and the reaction mixture was transferred to a separatory funnel for extraction. The extract was dried over MgSO4, concentrated, and the sample was purified by silica gel column chromatography to produce 5 g of compound 1-66. (Yield 48%, MS: [M+H] + =598)

[0944] Synthesis Example 1-67 [ka]

[0945] Dibenzo[b,d]furan-1-ylboronic acid (15 g, 70.8 mmol) and compound Trz57 (33 g, 74.3 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (29.3 g, 212.3 mmol) dissolved in 88 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.7 mmol) was added. After 5 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 26.5 g of compound 1-67_P1. (Yield: 65%, MS: [M+H] + =576)

[0946] Compound 1-67_P1 (10 g, 17.4 mmol), PtO2 (1.2 g, 5.2 mmol), and 87 ml of DO were placed in a shaker tube, sealed, and heated at 250°C and 600 psi for 12 hours. Upon completion of the reaction, chloroform was added and the reaction mixture was transferred to a separatory funnel for extraction. The extract was dried over MgSO4, concentrated, and the sample was purified by silica gel column chromatography to produce 4.4 g of compound 1-67. (Yield 42%, MS: [M+H] + =598)

[0947] Synthesis Example 1-68 [ka]

[0948] Dibenzo[b,d]furan-1-ylboronic acid (15 g, 70.8 mmol) and compound Trz58 (33 g, 74.3 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (29.3 g, 212.3 mmol) dissolved in 88 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.7 mmol) was added. After 4 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 26.5 g of compound 1-68_P1. (Yield: 65%, MS: [M+H] + =576)

[0949] Compound 1-68_P1 (10 g, 17.4 mmol), PtO2 (1.2 g, 5.2 mmol), and 87 ml of DO were placed in a shaker tube, sealed, and heated at 250°C and 600 psi for 12 hours. Upon completion of the reaction, chloroform was added and the reaction mixture was transferred to a separatory funnel for extraction. The extract was dried over MgSO4, concentrated, and the sample was purified by silica gel column chromatography to produce 3.6 g of compound 1-68. (Yield 35%, MS: [M+H] + =598)

[0950] (Synthesis scheme of compounds 2-AA to 2-AS) [ka]

[0951] Compounds 2-AA to 2-AS are as follows. [ka]

[0952] Preparation Example 2-1: Preparation of Compound 2-AA [ka]

[0953] In a nitrogen atmosphere, 1-bromo-3-chloronaphthalen-2-amine (15 g, 58.5 mmol) and benzoyl chloride (9.9 g, 70.2 mmol) were added to 300 mL of chloroform and stirred. Pyridine (6.9 g, 87.7 mmol) was then added dropwise. After reacting at room temperature for 9 hours, 600 mL of ethanol was added to solidify the mixture. The solid was filtered, then redissolved in chloroform and washed twice with water. The organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 17 g of compound 2-AA_P1. (Yield 81%, MS: [M+H] + =360)

[0954] Compound 2-AA_P1 (15 g, 41.6 mmol) and potassium carbonate (17.2 g, 124.8 mmol) were added to 150 mL of DMF under a nitrogen atmosphere and stirred and refluxed. After thorough stirring, copper iodide (0.1 g, 0.4 mmol) and 1,10-phenanthroline (0.1 g, 0.8 mmol) were added. After 11 hours of reaction, the mixture was cooled to room temperature and poured into 300 mL of water to solidify. The solid was filtered, redissolved in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 9.6 g of compound 2-AA. (Yield: 83%, MS: [M+H] + =280)

[0955] Preparation Example 2-2: Preparation of Compound 2-AB Compound 2-AB was prepared in the same manner as in Preparation Example 2-1, except that 1-bromo-4-chloronaphthalen-2-amine was used instead of 1-bromo-3-chloronaphthalen-2-amine.

[0956] Preparation Example 2-3: Preparation of Compound 2-AC Compound 2-AC was prepared in the same manner as in Preparation Example 2-1, except that 1-bromo-5-chloronaphthalen-2-amine was used instead of 1-bromo-3-chloronaphthalen-2-amine.

[0957] Preparation Example 2-4: Preparation of Compound 2-AD Compound 2-AD was prepared in the same manner as in Preparation Example 2-1, except that 1-bromo-6-chloronaphthalen-2-amine was used instead of 1-bromo-3-chloronaphthalen-2-amine.

[0958] Preparation Example 2-5: Preparation of Compound 2-AE Compound 2-AE was prepared in the same manner as in Preparation Example 2-1, except that 1-bromo-7-chloronaphthalen-2-amine was used instead of 1-bromo-3-chloronaphthalen-2-amine.

[0959] Preparation Example 2-6: Preparation of Compound 2-AF Compound 2-AF was prepared in the same manner as in Preparation Example 2-1, except that 1-bromo-8-chloronaphthalen-2-amine was used instead of 1-bromo-3-chloronaphthalen-2-amine.

[0960] Preparation Example 2-7: Preparation of Compound 2-AG Compound 2-AG was prepared in the same manner as in Preparation Example 2-1, except that [1,1'-biphenyl]-4-carbonyl chloride was used instead of benzoyl chloride.

[0961] Preparation Example 2-8: Preparation of Compound 2-AH Compound 2-AH was prepared in the same manner as in Preparation Example 2-1, except that [1,1'-biphenyl]-4-carbonyl chloride was used instead of benzoyl chloride and 1-bromo-4-chloronaphthalen-2-amine was used instead of 1-bromo-3-chloronaphthalen-2-amine.

[0962] Preparation Example 2-9: Preparation of Compound 2-AI Compound 2-AH was prepared in the same manner as in Preparation Example 2-1, except that [1,1'-biphenyl]-4-carbonyl chloride was used instead of benzoyl chloride and 1-bromo-5-chloronaphthalen-2-amine was used instead of 1-bromo-3-chloronaphthalen-2-amine.

[0963] Preparation Example 2-10: Preparation of Compound 2-AJ Compound 2-AJ was prepared in the same manner as in Preparation Example 2-1, except that [1,1'-biphenyl]-4-carbonyl chloride was used instead of benzoyl chloride and 1-bromo-6-chloronaphthalen-2-amine was used instead of 1-bromo-3-chloronaphthalen-2-amine.

[0964] Preparation Example 2-11: Preparation of Compound 2-AK Compound 2-AK was prepared in the same manner as in Preparation Example 2-1, except that [1,1'-biphenyl]-4-carbonyl chloride was used instead of benzoyl chloride and 1-bromo-7-chloronaphthalen-2-amine was used instead of 1-bromo-3-chloronaphthalen-2-amine.

[0965] Preparation Example 2-12: Preparation of Compound 2-AL Compound 2-AL was prepared in the same manner as in Preparation Example 2-1, except that [1,1'-biphenyl]-4-carbonyl chloride was used instead of benzoyl chloride and 1-bromo-8-chloronaphthalen-2-amine was used instead of 1-bromo-3-chloronaphthalen-2-amine.

[0966] Preparation Example 2-13: Preparation of Compound 2-AM Compound 2-AM was prepared in the same manner as in Preparation Example 2-1, except that 2-naphthoyl chloride was used instead of benzoyl chloride.

[0967] Preparation Example 2-14: Preparation of Compound 2-AN Compound 2-AN was prepared in the same manner as in Preparation Example 2-1, except that 2-naphthoyl chloride was used instead of benzoyl chloride and 1-bromo-4-chloronaphthalen-2-amine was used instead of 1-bromo-3-chloronaphthalen-2-amine.

[0968] Preparation Example 2-15: Preparation of Compound 2-AO Compound 2-AO was prepared in the same manner as in Preparation Example 2-1, except that 2-naphthoyl chloride was used instead of benzoyl chloride and 1-bromo-5-chloronaphthalen-2-amine was used instead of 1-bromo-3-chloronaphthalen-2-amine.

[0969] Preparation Example 2-16: Preparation of Compound 2-AP Compound 2-AP was prepared in the same manner as in Preparation Example 2-1, except that 2-naphthoyl chloride was used instead of benzoyl chloride and 1-bromo-6-chloronaphthalen-2-amine was used instead of 1-bromo-3-chloronaphthalen-2-amine.

[0970] Preparation Example 2-17: Preparation of Compound 2-AQ Compound 2-AQ was prepared in the same manner as in Preparation Example 2-1, except that 2-naphthoyl chloride was used instead of benzoyl chloride and 1-bromo-7-chloronaphthalen-2-amine was used instead of 1-bromo-3-chloronaphthalen-2-amine.

[0971] Preparation Example 2-18: Preparation of Compound 2-AR Compound 2-AR was prepared in the same manner as in Preparation Example 2-1, except that 2-naphthoyl chloride was used instead of benzoyl chloride and 1-bromo-8-chloronaphthalen-2-amine was used instead of 1-bromo-3-chloronaphthalen-2-amine.

[0972] Preparation Example 2-19: Preparation of Compound 2-AS Compound 2-AS was prepared in the same manner as in Preparation Example 2-1, except that 4-chlorobenzoyl chloride was used instead of benzoyl chloride and 1-bromonaphthalen-2-amine was used instead of 1-bromo-3-chloronaphthalen-2-amine.

[0973] (Synthesis scheme of compounds 2-BA to 2-BT) [ka]

[0974] Compounds 2-BA to 2-BT are as follows. [ka]

[0975] Preparation Example 2-20: Preparation of Compound 2-BA Compound 2-BA was prepared in the same manner as in Preparation Example 2-1, except that 2-bromo-3-chloronaphthalen-1-amine was used instead of 1-bromo-3-chloronaphthalen-2-amine.

[0976] Preparation Example 2-21: Preparation of Compound 2-BB Compound 2-BB was prepared in the same manner as in Preparation Example 2-1, except that 2-bromo-4-chloronaphthalen-1-amine was used instead of 1-bromo-3-chloronaphthalen-2-amine.

[0977] Preparation Example 2-22: Preparation of Compound 2-BC Compound 2-BC was prepared in the same manner as in Preparation Example 2-1, except that 2-bromo-5-chloronaphthalen-1-amine was used instead of 1-bromo-3-chloronaphthalen-2-amine.

[0978] Preparation Example 2-23: Preparation of Compound 2-BD Compound 2-BD was prepared in the same manner as in Preparation Example 2-1, except that 2-bromo-6-chloronaphthalen-1-amine was used instead of 1-bromo-3-chloronaphthalen-2-amine.

[0979] Preparation Example 2-24: Preparation of Compound 2-BE Compound 2-BE was prepared in the same manner as in Preparation Example 2-1, except that 2-bromo-7-chloronaphthalen-1-amine was used instead of 1-bromo-3-chloronaphthalen-2-amine.

[0980] Preparation Example 2-25: Preparation of Compound 2-BF Compound 2-BF was prepared in the same manner as in Preparation Example 2-1, except that 2-bromo-8-chloronaphthalen-1-amine was used instead of 1-bromo-3-chloronaphthalen-2-amine.

[0981] Preparation Example 2-26: Preparation of Compound 2-BG Compound 2-BG was prepared in the same manner as in Preparation Example 2-1, except that [1,1'-biphenyl]-4-carbonyl chloride was used instead of benzoyl chloride and 2-bromo-3-chloronaphthalen-1-amine was used instead of 1-bromo-3-chloronaphthalen-2-amine.

[0982] Preparation Example 2-27: Preparation of Compound 2-BH Compound 2-BH was prepared in the same manner as in Preparation Example 2-1, except that [1,1'-biphenyl]-4-carbonyl chloride was used instead of benzoyl chloride and 2-bromo-4-chloronaphthalen-1-amine was used instead of 1-bromo-3-chloronaphthalen-2-amine.

[0983] Preparation Example 2-28: Preparation of Compound 2-BI Compound 2-BI was prepared in the same manner as in Preparation Example 2-1, except that [1,1'-biphenyl]-4-carbonyl chloride was used instead of benzoyl chloride and 2-bromo-5-chloronaphthalen-1-amine was used instead of 1-bromo-3-chloronaphthalen-2-amine.

[0984] Preparation Example 2-29: Preparation of Compound 2-BJ Compound 2-BJ was prepared in the same manner as in Preparation Example 2-1, except that [1,1'-biphenyl]-4-carbonyl chloride was used instead of benzoyl chloride and 2-bromo-6-chloronaphthalen-1-amine was used instead of 1-bromo-3-chloronaphthalen-2-amine.

[0985] Preparation Example 2-30: Preparation of Compound 2-BK Compound 2-BK was prepared in the same manner as in Preparation Example 2-1, except that [1,1'-biphenyl]-4-carbonyl chloride was used instead of benzoyl chloride and 2-bromo-7-chloronaphthalen-1-amine was used instead of 1-bromo-3-chloronaphthalen-2-amine.

[0986] Preparation Example 2-31: Preparation of Compound 2-BL Compound 2-BL was prepared in the same manner as in Preparation Example 2-1, except that [1,1'-biphenyl]-4-carbonyl chloride was used instead of benzoyl chloride and 2-bromo-8-chloronaphthalen-1-amine was used instead of 1-bromo-3-chloronaphthalen-2-amine.

[0987] Preparation Example 2-32: Preparation of Compound 2-BM Compound 2-BM was prepared in the same manner as in Preparation Example 2-1, except that 2-naphthoyl chloride was used instead of benzoyl chloride and 2-bromo-3-chloronaphthalen-1-amine was used instead of 1-bromo-3-chloronaphthalen-2-amine.

[0988] Preparation Example 2-33: Preparation of Compound 2-BN Compound 2-BN was prepared in the same manner as in Preparation Example 2-1, except that 2-naphthoyl chloride was used instead of benzoyl chloride and 2-bromo-4-chloronaphthalen-1-amine was used instead of 1-bromo-3-chloronaphthalen-2-amine.

[0989] Preparation Example 2-34: Preparation of Compound 2-BO Compound 2-BO was prepared in the same manner as in Preparation Example 2-1, except that 2-naphthoyl chloride was used instead of benzoyl chloride and 2-bromo-5-chloronaphthalen-1-amine was used instead of 1-bromo-3-chloronaphthalen-2-amine.

[0990] Preparation Example 2-35: Preparation of Compound 2-BP Compound 2-BP was prepared in the same manner as in Preparation Example 2-1, except that 2-naphthoyl chloride was used instead of benzoyl chloride and 2-bromo-6-chloronaphthalen-1-amine was used instead of 1-bromo-3-chloronaphthalen-2-amine.

[0991] Preparation Example 2-36: Preparation of Compound 2-BQ Compound 2-BQ was prepared in the same manner as in Preparation Example 2-1, except that 2-naphthoyl chloride was used instead of benzoyl chloride and 2-bromo-7-chloronaphthalen-1-amine was used instead of 1-bromo-3-chloronaphthalen-2-amine.

[0992] Preparation Example 2-37: Preparation of Compound 2-BR Compound 2-BR was prepared in the same manner as in Preparation Example 2-1, except that 2-naphthoyl chloride was used instead of benzoyl chloride and 2-bromo-8-chloronaphthalen-1-amine was used instead of 1-bromo-3-chloronaphthalen-2-amine.

[0993] Preparation Example 2-38: Preparation of Compound 2-BS Compound 2-BS was prepared in the same manner as in Preparation Example 2-1, except that 4-chlorobenzoyl chloride was used instead of benzoyl chloride and 2-bromonaphthalen-1-amine was used instead of 1-bromo-3-chloronaphthalen-2-amine.

[0994] Preparation Example 2-39: Preparation of Compound 2-BT Compound 2-BT was prepared in the same manner as in Preparation Example 2-1, except that 4-chloro-1-naphthoyl chloride was used instead of benzoyl chloride and 2-bromonaphthalen-1-amine was used instead of 1-bromo-3-chloronaphthalen-2-amine.

[0995] Synthesis Example 2-1 [ka]

[0996] In a nitrogen atmosphere, compound 2-AA (10 g, 35.8 mmol), compound amine 1 (16 g, 35.8 mmol), and sodium tert-butoxide (11.4 g, 53.6 mmol) were added to 200 mL of xylene and stirred under reflux. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, the reaction was completed, and the mixture was cooled to room temperature and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform and washed twice with water. The organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 16.8 g of compound 2-1. (Yield: 68%, MS: [M+H] + =691)

[0997] Synthesis Example 2-2 [ka]

[0998] In a nitrogen atmosphere, compound 2-AB (10 g, 35.8 mmol), compound amine 2 (12.9 g, 35.8 mmol), and sodium tert-butoxide (11.4 g, 53.6 mmol) were added to 200 mL of xylene and stirred under reflux. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform and washed twice with water. The organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 13.2 g of compound 2-2. (Yield 61%, MS: [M+H] + =605)

[0999] Synthesis Example 2-3 [ka]

[1000] Compound 2-AC (10 g, 35.8 mmol), compound amine 3 (16 g, 35.8 mmol), and sodium tert-butoxide (11.4 g, 53.6 mmol) were added to 200 mL of xylene under a nitrogen atmosphere and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform and washed twice with water. The organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 17.3 g of compound 2-3. (Yield: 70%, MS: [M+H] + =691)

[1001] Synthesis Example 2-4 [ka]

[1002] Compound 2-AD (10 g, 35.8 mmol), compound amine 4 (10.6 g, 35.8 mmol), and sodium tert-butoxide (11.4 g, 53.6 mmol) were added to 200 mL of xylene under a nitrogen atmosphere and stirred under reflux. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform and washed twice with water. The organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 12.7 g of compound 2-4. (Yield: 66%, MS: [M+H] + =539)

[1003] Synthesis Example 2-5 [ka]

[1004] In a nitrogen atmosphere, compound 2-AE (10 g, 35.8 mmol), compound amine 5 (13.3 g, 35.8 mmol), and sodium tert-butoxide (11.4 g, 53.6 mmol) were added to 200 mL of xylene and stirred under reflux. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform and washed twice with water. The organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 13.4 g of compound 2-5. (Yield 61%, MS: [M+H] + =615)

[1005] Synthesis Example 2-6 [ka]

[1006] Compound 2-AE (10 g, 35.8 mmol), compound amine 6 (12 g, 35.8 mmol), and sodium tert-butoxide (11.4 g, 53.6 mmol) were added to 200 mL of xylene under a nitrogen atmosphere and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform and washed twice with water. The organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 13.4 g of compound 2-6. (Yield: 65%, MS: [M+H] + =579)

[1007] Synthesis Example 2-7 [ka]

[1008] In a nitrogen atmosphere, compound 2-AF (10 g, 35.8 mmol), compound amine 7 (12.3 g, 35.8 mmol), and sodium tert-butoxide (11.4 g, 53.6 mmol) were added to 200 mL of xylene and stirred under reflux. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform and washed twice with water. The organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 13.5 g of compound 2-7. (Yield: 64%, MS: [M+H] + =589)

[1009] Synthesis Example 2-8 [ka]

[1010] Compound 2-AA (15 g, 53.6 mmol) and compound amine 8 (25.6 g, 56.3 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (22.2 g, 160.9 mmol) dissolved in 67 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, and stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 23.9 g of compound 2-8. (Yield: 68%, MS: [M+H] + =655)

[1011] Synthesis Example 2-9 [ka]

[1012] Compound 2-AB (15 g, 53.6 mmol) and compound amine 9 (29.9 g, 56.3 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (22.2 g, 160.9 mmol) dissolved in 67 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, and stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 23.9 g of compound 2-9. (Yield: 61%, MS: [M+H] + =730)

[1013] Synthesis Example 2-10 [ka] Compound 2-AC (15 g, 53.6 mmol) and compound amine 10 (29.9 g, 56.3 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (22.2 g, 160.9 mmol) dissolved in 67 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After 12 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, and stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 24.2 g of compound 2-10. (Yield: 62%, MS: [M+H] + =730)

[1014] Synthesis Example 2-11 [ka]

[1015] Compound 2-AD (15 g, 53.6 mmol) and compound amine 11 (24.9 g, 56.3 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred and refluxed. Potassium carbonate (22.2 g, 160.9 mmol) dissolved in 67 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After 12 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, and stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 20.9 g of compound 2-11. (Yield 61%, MS: [M+H] + =641)

[1016] Synthesis Example 2-12 [ka]

[1017] Compound 2-AD (15 g, 53.6 mmol) and compound amine 12 (30.5 g, 56.3 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (22.2 g, 160.9 mmol) dissolved in 67 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 25.8 g of compound 2-12. (Yield: 65%, MS: [M+H] + =741)

[1018] Synthesis Example 2-13 [ka]

[1019] Compound 2-AE (15 g, 53.6 mmol) and compound amine 13 (21.4 g, 56.3 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred and refluxed. Potassium carbonate (22.2 g, 160.9 mmol) dissolved in 67 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 18.6 g of compound 2-13. (Yield: 60%, MS: [M+H] + =579)

[1020] Synthesis Example 2-14 [ka]

[1021] Compound 2-AE (15 g, 53.6 mmol) and compound amine 14 (23.4 g, 56.3 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (22.2 g, 160.9 mmol) dissolved in 67 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, and stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 22.1 g of compound 2-14. (Yield: 67%, MS: [M+H] + =615)

[1022] Synthesis Example 2-15 [ka]

[1023] Compound 2-AE (15 g, 53.6 mmol) and compound amine 15 (29.9 g, 56.3 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (22.2 g, 160.9 mmol) dissolved in 67 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 24.2 g of compound 2-15. (Yield: 62%, MS: [M+H] + =730)

[1024] Synthesis Example 2-16 [ka]

[1025] Compound 2-AE (15 g, 53.6 mmol) and compound amine 11 (24.9 g, 56.3 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred and refluxed. Potassium carbonate (22.2 g, 160.9 mmol) dissolved in 67 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, and stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 23 g of compound 2-16. (Yield: 67%, MS: [M+H] + =641)

[1026] Synthesis Example 2-17 [ka]

[1027] Compound 2-AF (15 g, 53.6 mmol) and compound amine 16 (27.9 g, 56.3 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (22.2 g, 160.9 mmol) dissolved in 67 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 23.5 g of compound 2-17. (Yield: 63%, MS: [M+H] + =695)

[1028] Synthesis Example 2-18 [ka]

[1029] Compound 2-AA (15 g, 53.6 mmol) and compound amine 17 (36.2 g, 56.3 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (22.2 g, 160.9 mmol) dissolved in 67 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 28.5 g of compound 2-18. (Yield 63%, MS: [M+H] + =843)

[1030] Synthesis Example 2-19 [ka]

[1031] Compound 2-AD (15 g, 53.6 mmol) and compound amine 18 (24.9 g, 56.3 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (22.2 g, 160.9 mmol) dissolved in 67 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, and stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 23.3 g of compound 2-19. (Yield: 68%, MS: [M+H] + =641)

[1032] Synthesis Example 2-20 [ka]

[1033] Compound 2-AF (15 g, 53.6 mmol) and compound amine 19 (34.8 g, 56.3 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (22.2 g, 160.9 mmol) dissolved in 67 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 27.6 g of compound 2-20. (Yield: 63%, MS: [M+H] + =817)

[1034] Synthesis Example 2-21 [ka]

[1035] Compound 2-AA (15 g, 53.6 mmol) and compound amine 20 (33.3 g, 56.3 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (22.2 g, 160.9 mmol) dissolved in 67 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 27.5 g of compound 2-21. (Yield: 65%, MS: [M+H] + =791)

[1036] Synthesis Example 2-22 [ka]

[1037] Compound A2-D (15 g, 53.6 mmol) and compound amine 21 (32 g, 56.3 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (22.2 g, 160.9 mmol) dissolved in 67 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After 12 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, and stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 27.9 g of compound 2-22. (Yield 68%, MS: [M+H] + =767)

[1038] Synthesis Example 2-23 [ka]

[1039] Compound 2-AE (15 g, 53.6 mmol) and compound amine 22 (23.4 g, 56.3 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (22.2 g, 160.9 mmol) dissolved in 67 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 22.4 g of compound 2-23. (Yield 68%, MS: [M+H] + =615)

[1040] Synthesis Example 2-24 [ka]

[1041] In a nitrogen atmosphere, compound 2-AH (10 g, 28.1 mmol), compound amine 23 (11.2 g, 28.1 mmol), and sodium tert-butoxide (8.9 g, 42.2 mmol) were added to 200 mL of xylene and stirred under reflux. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform and washed twice with water. The organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 14.1 g of compound 2-24. (Yield 70%, MS: [M+H] + =717)

[1042] Synthesis Example 2-25 [ka]

[1043] Compound 2-AJ (10 g, 28.1 mmol), compound amine 24 (12.6 g, 28.1 mmol), and sodium tert-butoxide (8.9 g, 42.2 mmol) were added to 200 mL of xylene under a nitrogen atmosphere and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform and washed twice with water. The organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 13.1 g of compound 2-25. (Yield 61%, MS: [M+H] + =767)

[1044] Synthesis Example 2-26 [ka]

[1045] Compound 2-AJ (10 g, 28.1 mmol), compound amine 25 (10.4 g, 28.1 mmol), and sodium tert-butoxide (8.9 g, 42.2 mmol) were added to 200 mL of xylene under a nitrogen atmosphere and stirred under reflux. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform and washed twice with water. The organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 11.8 g of compound 2-26. (Yield: 61%, MS: [M+H] + =691)

[1046] Synthesis Example 2-27 [ka]

[1047] In a nitrogen atmosphere, compound 2-AK (10 g, 28.1 mmol), compound amine 26 (9.8 g, 28.1 mmol), and sodium tert-butoxide (8.9 g, 42.2 mmol) were added to 200 mL of xylene and stirred under reflux. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform and washed twice with water. The organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 11.6 g of compound 2-27. (Yield: 62%, MS: [M+H] + =669)

[1048] Synthesis Example 2-28 [ka]

[1049] Compound 2-AK (15 g, 42.2 mmol) and compound amine 27 (16.2 g, 44.3 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (17.5 g, 126.5 mmol) dissolved in 52 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.4 mmol) was added. After 12 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 16.2 g of compound 2-28. (Yield: 60%, MS: [M+H] + =641)

[1050] Synthesis Example 2-29 [ka]

[1051] Compound 2-AI (15 g, 42.2 mmol) and compound amine 28 (19.5 g, 44.3 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (17.5 g, 126.5 mmol) dissolved in 52 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.4 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 18.1 g of compound 2-29. (Yield: 60%, MS: [M+H]+ =717)

[1052] Synthesis Example 2-30 [ka]

[1053] Compound 2-AG (15 g, 42.2 mmol) and compound amine 29 (25.1 g, 44.3 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (17.5 g, 126.5 mmol) dissolved in 52 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.4 mmol) was added. After 12 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 22.7 g of compound 2-30. (Yield: 64%, MS: [M+H] + =843)

[1054] Synthesis Example 2-31 [ka]

[1055] Compound 2-AJ (15 g, 42.2 mmol) and compound amine 30 (22.9 g, 44.3 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (17.5 g, 126.5 mmol) dissolved in 52 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.4 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, and stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 22.4 g of compound 2-31. (Yield: 67%, MS: [M+H] + =793)

[1056] Synthesis Example 2-32 [ka]

[1057] Compound 2-AI (15 g, 42.2 mmol) and compound amine 31 (21.8 g, 44.3 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (17.5 g, 126.5 mmol) dissolved in 52 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.4 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, and stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 22.6 g of compound 2-32. (Yield 70%, MS: [M+H] + =767)

[1058] Synthesis Example 2-33 [ka]

[1059] Compound 2-AL (15 g, 42.2 mmol) and compound amine 32 (22.9 g, 44.3 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (17.5 g, 126.5 mmol) dissolved in 52 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.4 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 23.4 g of compound 2-33. (Yield 70%, MS: [M+H] + =793)

[1060] Synthesis Example 2-34 [ka]

[1061] Compound 2-AK (15 g, 42.2 mmol) and compound amine 33 (25.1 g, 44.3 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (17.5 g, 126.5 mmol) dissolved in 52 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.4 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 21.3 g of compound 2-34. (Yield: 60%, MS: [M+H] + =843)

[1062] Synthesis Example 2-35 [ka]

[1063] Compound 2-AI (15 g, 42.2 mmol) and compound amine 34 (22.4 g, 44.3 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (17.5 g, 126.5 mmol) dissolved in 52 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.4 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, and stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 22.7 g of compound 2-35. (Yield: 69%, MS: [M+H] + =781)

[1064] Synthesis Example 2-36 [ka]

[1065] Compound 2-AH (15 g, 42.2 mmol) and compound amine 35 (22.8 g, 44.3 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (17.5 g, 126.5 mmol) dissolved in 52 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.4 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 23 g of compound 2-36. (Yield: 69%, MS: [M+H] + =791)

[1066] Synthesis Example 2-37 [ka]

[1067] In a nitrogen atmosphere, compound 2-AQ (10 g, 30.3 mmol), compound amine 36 (11.1 g, 30.3 mmol), and sodium tert-butoxide (9.7 g, 45.5 mmol) were added to 200 mL of xylene and stirred under reflux. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform and washed twice with water. The organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 13.6 g of compound 2-37. (Yield: 68%, MS: [M+H] + =659)

[1068] Synthesis Example 2-38 [ka]

[1069] In a nitrogen atmosphere, compound 2-AO (10 g, 30.3 mmol), compound amine 37 (13.6 g, 30.3 mmol), and sodium tert-butoxide (9.7 g, 45.5 mmol) were added to 200 mL of xylene and stirred under reflux. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform and washed twice with water. The organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 14.4 g of compound 2-38. (Yield: 64%, MS: [M+H] + =741)

[1070] Synthesis Example 2-39 [ka]

[1071] Compound 2-AQ (10 g, 30.3 mmol), compound amine 38 (10.2 g, 30.3 mmol), and sodium tert-butoxide (9.7 g, 45.5 mmol) were added to 200 mL of xylene under a nitrogen atmosphere and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform and washed twice with water. The organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 12 g of compound 2-39. (Yield: 63%, MS: [M+H] + =629)

[1072] Synthesis Example 2-40 [ka]

[1073] Compound 2-AQ (15 g, 45.5 mmol) and compound amine 27 (17.4 g, 47.8 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (18.9 g, 136.5 mmol) dissolved in 57 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.5 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, and stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 18.4 g of compound 2-40. (Yield: 66%, MS: [M+H] + =615)

[1074] Synthesis Example 2-41 [ka]

[1075] Compound 2-AN (15 g, 45.5 mmol) and compound amine 39 (24.7 g, 47.8 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (18.9 g, 136.5 mmol) dissolved in 57 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.5 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 20.9 g of compound 2-41. (Yield: 60%, MS: [M+H] + =767)

[1076] Synthesis Example 2-42 [ka]

[1077] Compound 2-AR (15 g, 45.5 mmol) and compound amine 40 (21.1 g, 47.8 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (18.9 g, 136.5 mmol) dissolved in 57 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.5 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 20.7 g of compound 2-42. (Yield: 66%, MS: [M+H] + =691)

[1078] Synthesis Example 2-43 [ka]

[1079] Compound 2-AP (15 g, 45.5 mmol) and compound amine 41 (27.8 g, 47.8 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (18.9 g, 136.5 mmol) dissolved in 57 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.5 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, and stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 26.1 g of compound 2-43. (Yield: 69%, MS: [M+H] + =831)

[1080] Synthesis Example 2-44 [ka]

[1081] Compound 2-AQ (15 g, 45.5 mmol) and compound amine 42 (23.5 g, 47.8 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (18.9 g, 136.5 mmol) dissolved in 57 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.5 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 22.9 g of compound 2-44. (Yield: 68%, MS: [M+H] + =741)

[1082] Synthesis Example 2-45 [ka]

[1083] Compound 2-AN (15 g, 45.5 mmol) and compound amine 43 (27.1 g, 47.8 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred and refluxed. Potassium carbonate (18.9 g, 136.5 mmol) dissolved in 57 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.5 mmol) was added. After 12 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 26 g of compound 2-45. (Yield 70%, MS: [M+H] + =817)

[1084] Synthesis Example 2-46 [ka]

[1085] Compound 2-AQ (15 g, 45.5 mmol) and compound amine 44 (27.1 g, 47.8 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (18.9 g, 136.5 mmol) dissolved in 57 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.5 mmol) was added. After 12 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 22.3 g of compound 2-46. (Yield: 60%, MS: [M+H] + =817)

[1086] Synthesis Example 2-47 [ka]

[1087] Compound 2-AO (15 g, 43.4 mmol) and compound amine 45 (25.8 g, 45.5 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (18 g, 130.1 mmol) dissolved in 54 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.4 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, and stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 19.5 g of compound 2-47. (Yield: 54%, MS: [M+H] + =833)

[1088] Synthesis Example 2-48 [ka]

[1089] Compound 2-AP (15 g, 45.5 mmol) and compound amine 46 (23.5 g, 47.8 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (18.9 g, 136.5 mmol) dissolved in 57 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.5 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 20.2 g of compound 2-48. (Yield: 60%, MS: [M+H] + =741)

[1090] Synthesis Example 2-49 [ka]

[1091] Compound 2-AN (15 g, 45.5 mmol) and compound amine 47 (23.5 g, 47.8 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred and refluxed. Potassium carbonate (18.9 g, 136.5 mmol) dissolved in 57 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.5 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 21.5 g of compound 2-49. (Yield: 64%, MS: [M+H] + =741)

[1092] Synthesis Example 2-50 [ka]

[1093] In a nitrogen atmosphere, compound 2-BA (10 g, 30.3 mmol), compound amine 48 (12.1 g, 30.3 mmol), and sodium tert-butoxide (9.7 g, 45.5 mmol) were added to 200 mL of xylene and stirred under reflux. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform and washed twice with water. The organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 11.8 g of compound 2-50. (Yield: 61%, MS: [M+H] + =641)

[1094] Synthesis Example 2-51 [ka]

[1095] In a nitrogen atmosphere, compound 2-BA (10 g, 30.3 mmol), compound amine 49 (11.3 g, 30.3 mmol), and sodium tert-butoxide (9.7 g, 45.5 mmol) were added to 200 mL of xylene and stirred under reflux. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform and washed twice with water. The organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 11.7 g of compound 2-51. (Yield 63%, MS: [M+H] + =615)

[1096] Synthesis Example 2-52 [ka]

[1097] In a nitrogen atmosphere, compound 2-BB (10 g, 30.3 mmol), compound amine 50 (12.9 g, 30.3 mmol), and sodium tert-butoxide (9.7 g, 45.5 mmol) were added to 200 mL of xylene and stirred under reflux. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform and washed twice with water. The organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 14 g of compound 2-52. (Yield 69%, MS: [M+H] + =668)

[1098] Synthesis Example 2-53 [ka]

[1099] In a nitrogen atmosphere, compound 2-BC (10 g, 30.3 mmol), compound amine 51 (14 g, 30.3 mmol), and sodium tert-butoxide (9.7 g, 45.5 mmol) were added to 200 mL of xylene and stirred under reflux. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform and washed twice with water. The organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 12.8 g of compound 2-53. (Yield: 60%, MS: [M+H] + =704)

[1100] Synthesis Example 2-54 [ka]

[1101] Compound 2-BD (10 g, 30.3 mmol), compound amine 52 (13.6 g, 30.3 mmol), and sodium tert-butoxide (9.7 g, 45.5 mmol) were added to 200 mL of xylene under a nitrogen atmosphere and stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform and washed twice with water. The organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 12.6 g of compound 2-54. (Yield 60%, MS: [M+H] + =691)

[1102] Synthesis Example 2-55 [ka]

[1103] In a nitrogen atmosphere, compound 2-BE (10 g, 30.3 mmol), compound amine 53 (12.1 g, 30.3 mmol), and sodium tert-butoxide (9.7 g, 45.5 mmol) were added to 200 mL of xylene and stirred under reflux. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform and washed twice with water. The organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 13.2 g of compound 2-55. (Yield 68%, MS: [M+H] + =641)

[1104] Synthesis Example 2-56 [ka] Compound 2-BA (15 g, 53.6 mmol) and compound amine 54 (27.1 g, 56.3 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (22.2 g, 160.9 mmol) dissolved in 67 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 21.9 g of compound 2-56. (Yield: 60%, MS: [M+H] + =681)

[1105] Synthesis Example 2-57 [ka]

[1106] Compound 2-BC (15 g, 53.6 mmol) and compound amine 55 (26.5 g, 56.3 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (22.2 g, 160.9 mmol) dissolved in 67 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 23 g of compound 2-57. (Yield: 64%, MS: [M+H] + =671)

[1107] Synthesis Example 2-58 [ka]

[1108] Compound 2-BC (15 g, 53.6 mmol) and compound amine 56 (24.9 g, 56.3 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (22.2 g, 160.9 mmol) dissolved in 67 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 22.7 g of compound 2-58. (Yield: 66%, MS: [M+H] + =641)

[1109] Synthesis Example 2-59 [ka]

[1110] Compound 2-BE (15 g, 53.6 mmol) and compound amine 57 (22.3 g, 56.3 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (22.2 g, 160.9 mmol) dissolved in 67 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, and stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 22.3 g of compound 2-59. (Yield: 70%, MS: [M+H] + =595)

[1111] Synthesis Example 2-60 [ka]

[1112] Compound 2-BF (15 g, 53.6 mmol) and compound amine 58 (32.7 g, 56.3 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (22.2 g, 160.9 mmol) dissolved in 67 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, and stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 25.5 g of compound 2-60. (Yield 61%, MS: [M+H] + =780)

[1113] Synthesis Example 2-61 [ka]

[1114] Compound 2-BE (15 g, 53.6 mmol) and compound amine 59 (36.2 g, 56.3 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (22.2 g, 160.9 mmol) dissolved in 67 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, and stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 31.6 g of compound 2-61. (Yield 70%, MS: [M+H] + =843)

[1115] Synthesis Example 2-62 [ka]

[1116] Compound 2-BC (15 g, 53.6 mmol) and compound amine 60 (29.9 g, 56.3 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (22.2 g, 160.9 mmol) dissolved in 67 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After 12 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, and stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 26.2 g of compound 2-62. (Yield 67%, MS: [M+H] + =730)

[1117] Synthesis Example 2-63 [ka]

[1118] Compound 2-BD (15 g, 53.6 mmol) and compound amine 61 (27.7 g, 56.3 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (22.2 g, 160.9 mmol) dissolved in 67 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 22.2 g of compound 2-63. (Yield: 60%, MS: [M+H] + =691)

[1119] Synthesis Example 2-64 [ka]

[1120] Compound 2-BE (15 g, 53.6 mmol) and compound amine 62 (23.4 g, 56.3 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (22.2 g, 160.9 mmol) dissolved in 67 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, and stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 21.1 g of compound 2-64. (Yield: 64%, MS: [M+H] + =615)

[1121] Synthesis Example 2-65 [ka]

[1122] Compound 2-BD (15 g, 53.6 mmol) and compound amine 63 (22.8 g, 56.3 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (22.2 g, 160.9 mmol) dissolved in 67 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, and stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 21.7 g of compound 2-65. (Yield 67%, MS: [M+H] + =605)

[1123] Synthesis Example 2-66 [ka]

[1124] Compound 2-BF (15 g, 53.6 mmol) and compound amine 64 (31.6 g, 56.3 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (22.2 g, 160.9 mmol) dissolved in 67 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 26.9 g of compound 2-66. (Yield 66%, MS: [M+H] + =760)

[1125] Synthesis Example 2-67 [ka]

[1126] Compound 2-BB (15 g, 53.6 mmol) and compound amine 65 (32 g, 56.3 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (22.2 g, 160.9 mmol) dissolved in 67 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, and stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 27.1 g of compound 2-67. (Yield 66%, MS: [M+H] + =767)

[1127] Synthesis Example 2-68 [ka]

[1128] Compound 2-BC (15 g, 53.6 mmol) and compound amine 66 (32 g, 56.3 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (22.2 g, 160.9 mmol) dissolved in 67 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 19.8 g of compound 2-68. (Yield 65%, MS: [M+H] + =569)

[1129] Synthesis Example 2-69 [ka] Compound 2-BB (15 g, 53.6 mmol) and compound amine 67 (29.1 g, 56.3 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (22.2 g, 160.9 mmol) dissolved in 67 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 26.5 g of compound 2-69. (Yield 69%, MS: [M+H]+ =717)

[1130] Synthesis Example 2-70 [ka]

[1131] Compound 2-BF (15 g, 53.6 mmol) and compound amine 68 (30.5 g, 56.3 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (22.2 g, 160.9 mmol) dissolved in 67 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After 12 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 25 g of compound 2-70. (Yield: 63%, MS: [M+H] + =741)

[1132] Synthesis Example 2-71 [ka]

[1133] Compound 2-BC (15 g, 53.6 mmol) and compound amine 69 (26.2 g, 56.3 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (22.2 g, 160.9 mmol) dissolved in 67 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, and stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 22.1 g of compound 2-71. (Yield: 62%, MS: [M+H] + =665)

[1134] Synthesis Example 2-72 [ka]

[1135] Compound 2-BF (15 g, 53.6 mmol) and compound amine 70 (23.4 g, 56.3 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (22.2 g, 160.9 mmol) dissolved in 67 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, and stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 21.7 g of compound 2-72. (Yield: 66%, MS: [M+H] + =615)

[1136] Synthesis Example 2-73 [ka]

[1137] Compound 2-BE (15 g, 53.6 mmol) and compound amine 71 (32 g, 56.3 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (22.2 g, 160.9 mmol) dissolved in 67 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 25.5 g of compound 2-73. (Yield: 62%, MS: [M+H] + =767)

[1138] Synthesis Example 2-74 [ka]

[1139] Compound 2-BD (15 g, 53.6 mmol) and compound amine 72 (36.2 g, 56.3 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (22.2 g, 160.9 mmol) dissolved in 67 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 30.7 g of compound 2-74. (Yield: 68%, MS: [M+H] + =843)

[1140] Synthesis Example 2-75 [ka] Compound 2-BC (15 g, 53.6 mmol) and compound amine 73 (39.1 g, 56.3 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (22.2 g, 160.9 mmol) dissolved in 67 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.6 g, 0.5 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 29.7 g of compound 2-75. (Yield: 62%, MS: [M+H] + =893)

[1141] Synthesis Example 2-76 [ka]

[1142] In a nitrogen atmosphere, compound 2-BG (10 g, 28.1 mmol), compound amine 74 (10.4 g, 28.1 mmol), and sodium tert-butoxide (8.9 g, 42.2 mmol) were added to 200 mL of xylene and stirred under reflux. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform and washed twice with water. The organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 12.6 g of compound 2-76. (Yield: 65%, MS: [M+H] +=691)

[1143] Synthesis Example 2-77 [ka]

[1144] In a nitrogen atmosphere, compound 2-BI (10 g, 28.1 mmol), compound amine 75 (9.4 g, 28.1 mmol), and sodium tert-butoxide (8.9 g, 42.2 mmol) were added to 200 mL of xylene and stirred under reflux. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform and washed twice with water. The organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 11 g of compound 2-77. (Yield: 60%, MS: [M+H] + =655)

[1145] Synthesis Example 2-78 [ka]

[1146] In a nitrogen atmosphere, compound 2-BJ (10 g, 28.1 mmol), compound amine 76 (10.4 g, 28.1 mmol), and sodium tert-butoxide (8.9 g, 42.2 mmol) were added to 200 mL of xylene and stirred under reflux. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform and washed twice with water. The organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 11.8 g of compound 2-78. (Yield: 61%, MS: [M+H]+ =691)

[1147] Synthesis Example 2-79 [ka]

[1148] In a nitrogen atmosphere, compound 2-BK (10 g, 28.1 mmol), compound amine 77 (11.8 g, 28.1 mmol), and sodium tert-butoxide (8.9 g, 42.2 mmol) were added to 200 mL of xylene and stirred under reflux. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform and washed twice with water. The organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 13.1 g of compound 2-79. (Yield: 63%, MS: [M+H] + =741)

[1149] Synthesis Example 2-80 [ka]

[1150] Compound 2-BJ (15 g, 42.2 mmol) and compound amine 78 (16.2 g, 44.3 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (17.5 g, 126.5 mmol) dissolved in 52 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.4 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, and stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 18.1 g of compound 2-80. (Yield: 67%, MS: [M+H] + =641)

[1151] Synthesis Example 2-81 [ka]

[1152] Compound 2-BG (15 g, 42.2 mmol) and compound amine 79 (21.8 g, 44.3 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (17.5 g, 126.5 mmol) dissolved in 52 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.4 mmol) was added. After 11.5 hours of stirring, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, and stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 19.7 g of compound 2-81. (Yield: 61%, MS: [M+H] + =767)

[1153] Synthesis Example 2-82 [ka]

[1154] Compound 2-BI (15 g, 42.2 mmol) and compound amine 80 (26.3 g, 44.3 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (17.5 g, 126.5 mmol) dissolved in 52 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.4 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 24.9 g of compound 2-82. (Yield: 68%, MS: [M+H] + =869)

[1155] Synthesis Example 2-83 [ka]

[1156] Compound 2-BH (15 g, 42.2 mmol) and compound amine 81 (20.2 g, 44.3 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (17.5 g, 126.5 mmol) dissolved in 52 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.4 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, and stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 19.7 g of compound 2-83. (Yield: 64%, MS: [M+H] + =731)

[1157] Synthesis Example 2-84 [ka]

[1158] Compound 2-BG (15 g, 42.2 mmol) and compound amine 82 (21.8 g, 44.3 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred and refluxed. Potassium carbonate (17.5 g, 126.5 mmol) dissolved in 52 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.4 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 20 g of compound 2-84. (Yield: 62%, MS: [M+H] + =767)

[1159] Synthesis Example 2-85 [ka]

[1160] Compound 2-BL (15 g, 42.2 mmol) and compound amine 83 (22.9 g, 44.3 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred and refluxed. Potassium carbonate (17.5 g, 126.5 mmol) dissolved in 52 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.4 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 20 g of compound 2-85. (Yield: 60%, MS: [M+H] + =793)

[1161] Synthesis Example 2-86 [ka]

[1162] Compound 2-BG (15 g, 42.2 mmol) and compound amine 84 (23.5 g, 44.3 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (17.5 g, 126.5 mmol) dissolved in 52 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.4 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, and stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 23.5 g of compound 2-86. (Yield: 69%, MS: [M+H] + =807)

[1163] Synthesis Example 2-87 [ka]

[1164] Compound 2-BI (15 g, 42.2 mmol) and compound amine 85 (22.4 g, 44.3 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (17.5 g, 126.5 mmol) dissolved in 52 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.4 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, and stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 22.7 g of compound 2-87. (Yield: 69%, MS: [M+H] + =781)

[1165] Synthesis Example 2-88 [ka]

[1166] Compound 2-BJ (15 g, 42.2 mmol) and compound amine 86 (20.6 g, 44.3 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (17.5 g, 126.5 mmol) dissolved in 52 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.4 mmol) was added. After 12 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, and stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 20.6 g of compound 2-88. (Yield: 66%, MS: [M+H] + =741)

[1167] Synthesis Example 2-89 [ka]

[1168] Compound 2-BI (15 g, 42.2 mmol) and compound amine 87 (22.4 g, 44.3 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (17.5 g, 126.5 mmol) dissolved in 52 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.4 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 20.4 g of compound 2-89. (Yield: 62%, MS: [M+H] + =781)

[1169] Synthesis Example 2-90 [ka]

[1170] In a nitrogen atmosphere, compound 2-BN (10 g, 30.3 mmol), compound amine 88 (11.3 g, 30.3 mmol), and sodium tert-butoxide (9.7 g, 45.5 mmol) were added to 200 mL of xylene and stirred under reflux. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform and washed twice with water. The organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 13.3 g of compound 2-90. (Yield: 66%, MS: [M+H] + =665)

[1171] Synthesis Example 2-91 [ka]

[1172] In a nitrogen atmosphere, compound 2-BM (10 g, 30.3 mmol), compound amine 89 (12.8 g, 30.3 mmol), and sodium tert-butoxide (9.7 g, 45.5 mmol) were added to 200 mL of xylene and stirred under reflux. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform and washed twice with water. The organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 13.4 g of compound 2-91. (Yield: 62%, MS: [M+H] + =715)

[1173] Synthesis Example 2-92 [ka]

[1174] In a nitrogen atmosphere, compound 2-BP (10 g, 30.3 mmol), compound amine 90 (12.1 g, 30.3 mmol), and sodimut-butoxide (9.7 g, 45.5 mmol) were added to 200 mL of xylene and stirred under reflux. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform and washed twice with water. The organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 13.8 g of compound 2-92. (Yield: 66%, MS: [M+H] + =691)

[1175] Synthesis Example 2-93 [ka]

[1176] In a nitrogen atmosphere, compound 2-BQ (10 g, 30.3 mmol), compound amine 91 (12.1 g, 30.3 mmol), and sodium tert-butoxide (9.7 g, 45.5 mmol) were added to 200 mL of xylene and stirred under reflux. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform and washed twice with water. The organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 13.4 g of compound 2-93. (Yield: 64%, MS: [M+H] + =691)

[1177] Synthesis Example 2-94 [ka]

[1178] Compound 2-BP (15 g, 45.5 mmol) and compound amine 92 (25.6 g, 47.8 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (18.9 g, 136.5 mmol) dissolved in 57 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.5 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 21.8 g of compound 2-94. (Yield: 61%, MS: [M+H] + =785)

[1179] Synthesis Example 2-95 [ka]

[1180] Compound 2-BN (15 g, 45.5 mmol) and compound amine 93 (26 g, 47.8 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (18.9 g, 136.5 mmol) dissolved in 57 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.5 mmol) was added. After 9 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, and stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 24.6 g of compound 2-95. (Yield: 68%, MS: [M+H] + =795)

[1181] Synthesis Example 2-96 [ka]

[1182] Compound 2-BP (15 g, 45.5 mmol) and compound amine 94 (27.1 g, 47.8 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (18.9 g, 136.5 mmol) dissolved in 57 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.5 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, and stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 25.6 g of compound 2-96. (Yield: 69%, MS: [M+H] + =817)

[1183] Synthesis Example 2-97 [ka]

[1184] Compound 2-BN (15 g, 45.5 mmol) and compound amine 95 (30.7 g, 47.8 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (18.9 g, 136.5 mmol) dissolved in 57 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.5 mmol) was added. After 12 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, and stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 25.2 g of compound 2-97. (Yield: 62%, MS: [M+H] +=893)

[1185] Synthesis Example 2-98 [ka]

[1186] Compound 2-BR (15 g, 45.5 mmol) and compound amine 96 (21.1 g, 47.8 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (18.9 g, 136.5 mmol) dissolved in 57 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.5 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 20.1 g of compound 2-98. (Yield: 64%, MS: [M+H] + =691)

[1187] Synthesis Example 2-99 [ka]

[1188] Compound 2-BP (15 g, 45.5 mmol) and compound amine 97 (27.1 g, 47.8 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (18.9 g, 136.5 mmol) dissolved in 57 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.5 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, and stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 23 g of compound 2-99. (Yield: 62%, MS: [M+H] + =817)

[1189] Synthesis Example 2-100 [ka]

[1190] Compound 2-BN (15 g, 45.5 mmol) and compound amine 98 (24.7 g, 47.8 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (18.9 g, 136.5 mmol) dissolved in 57 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.5 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, and stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 22.3 g of compound 2-100. (Yield: 64%, MS: [M+H] + =767)

[1191] Synthesis Example 2-101 [ka]

[1192] Compound 2-BP (15 g, 45.5 mmol) and compound amine 99 (27.1 g, 47.8 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred and refluxed. Potassium carbonate (18.9 g, 136.5 mmol) dissolved in 57 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.5 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 22.3 g of compound 2-101. (Yield: 60%, MS: [M+H] + =817)

[1193] Synthesis Example 2-102 [ka]

[1194] Compound 2-BM (15 g, 45.5 mmol) and compound amine 100 (25.9 g, 47.8 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (18.9 g, 136.5 mmol) dissolved in 57 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.5 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 21.6 g of compound 2-102. (Yield: 60%, MS: [M+H] + =791)

[1195] Synthesis Example 2-103 [ka]

[1196] Compound 2-BO (15 g, 45.5 mmol) and compound amine 101 (27.1 g, 47.8 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (18.9 g, 136.5 mmol) dissolved in 57 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.5 mmol) was added. After 8 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 26 g of compound 2-103. (Yield: 70%, MS: [M+H] + =817)

[1197] Synthesis Example 2-104 [ka]

[1198] Compound 2-BO (15 g, 45.5 mmol) and compound amine 102 (24.1 g, 47.8 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (18.9 g, 136.5 mmol) dissolved in 57 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.5 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 22.6 g of compound 2-104. (Yield: 63%, MS: [M+H] + =791)

[1199] Synthesis Example 2-105 [ka]

[1200] Compound 2-BN (15 g, 45.5 mmol) and compound amine 103 (27.1 g, 47.8 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (18.9 g, 136.5 mmol) dissolved in 57 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.5 mmol) was added. After 11 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 23.7 g of compound 2-105. (Yield: 69%, MS: [M+H] + =755)

[1201] Synthesis Example 2-106 [ka]

[1202] In a nitrogen atmosphere, compound 2-AS (10 g, 35.8 mmol), compound amine 104 (13.8 g, 35.8 mmol), and sodium tert-butoxide (11.4 g, 53.6 mmol) were added to 200 mL of xylene and stirred under reflux. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 3 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform and washed twice with water. The organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 14.1 g of compound 2-106. (Yield: 63%, MS: [M+H] + =629)

[1203] Synthesis Example 2-107 [ka]

[1204] Compound 2-AS (15 g, 45.5 mmol) and compound amine 105 (21.2 g, 47.8 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred under reflux. Potassium carbonate (18.9 g, 136.5 mmol) dissolved in 57 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.5 mmol) was added. After 12 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, added with anhydrous magnesium sulfate, and stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 19.2 g of compound 2-107. (Yield: 61%, MS: [M+H] + =691)

[1205] Synthesis Example 2-108 [ka]

[1206] In a nitrogen atmosphere, compound 2-BS (15 g, 53.6 mmol), compound amine 106 (23.1 g, 56.3 mmol), and sodium tert-butoxide (7.7 g, 80.4 mmol) were added to 300 mL of xylene and stirred under reflux. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. The compound was then completely dissolved again in chloroform and washed twice with water. The organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 22.4 g of compound 2-108. (Yield: 64%, MS: [M+H] + =654)

[1207] Synthesis Example 2-109 [ka]

[1208] Compound 2-BT (15 g, 45.5 mmol) and compound amine 107 (21.2 g, 47.8 mmol) were added to 300 mL of THF under a nitrogen atmosphere and stirred and refluxed. Potassium carbonate (18.9 g, 136.5 mmol) dissolved in 57 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.5 mmol) was added. After 12 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 19.2 g of compound 2-109. (Yield: 61%, MS: [M+H] + =691)

[1209] Synthesis Example 3-1 [ka]

[1210] 1-bromo-7-chloronaphthalen-2-ol (15 g, 58.3 mmol) and (2-fluorophenyl)boronic acid (8.6 g, 61.2 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (24.2 g, 174.8 mmol) dissolved in 72 mL of water was then added. After thorough stirring, Tetrakis(triphenylphosphine)palladium(0) (0.7 g, 0.6 mmol) was added. After 6 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, added to anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 12.4 g of compound A_P1. (Yield 78%, MS: [M+H] + =273)

[1211] Compound A_P1 (15 g, 55 mmol) and potassium carbonate (22.8 g, 165 mmol) were added to 150 ml of DMAc and stirred under reflux. After reacting for 5 hours, the mixture was cooled to room temperature and poured into 300 ml of water to solidify. The solid was then filtered to obtain a solid. This was then dissolved again in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 8.5 g of compound A. (Yield 61%, MS: [M+H] + =253)

[1212] Compound A (15 g, 59.4 mmol) and compound amine 3-1 (30.6 g, 62.3 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (24.6 g, 178.1 mmol) dissolved in 74 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 27.6 g of compound 3-1. (Yield 70%, MS: [M+H] + =664)

[1213] Synthesis Example 3-2 [ka]

[1214] Compound A (15 g, 59.4 mmol) and compound amine 3-2 (27.5 g, 62.3 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (24.6 g, 178.1 mmol) dissolved in 74 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 3 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 26.2 g of compound 3-2. (Yield 72%, MS: [M+H] + =614)

[1215] Synthesis Example 3-3 [ka]

[1216] Compound A (15 g, 59.4 mmol) and compound amine 3-3 (25.9 g, 62.3 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (24.6 g, 178.1 mmol) dissolved in 74 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 23.4 g of compound 3-3. (Yield 67%, MS: [M+H] + =588)

[1217] Synthesis Example 3-4 [ka]

[1218] Compound A (15 g, 59.4 mmol) and compound amine 3-4 (23.6 g, 62.3 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (24.6 g, 178.1 mmol) dissolved in 74 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 24.2 g of compound 3-4. (Yield 74%, MS: [M+H] + =552)

[1219] Synthesis Example 3-5 [ka]

[1220] Compound A (15 g, 59.4 mmol) and compound amine 3-5 (32.3 g, 62.3 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (24.6 g, 178.1 mmol) dissolved in 74 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 3 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 26.6 g of compound 3-5. (Yield: 65%, MS: [M+H] + =690)

[1221] Synthesis Example 3-6 [ka]

[1222] Compound A (15 g, 59.4 mmol) and compound amine 3-6 (30.6 g, 62.3 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (24.6 g, 178.1 mmol) dissolved in 74 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 3 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 29.1 g of compound 3-6. (Yield 74%, MS: [M+H] + =664)

[1223] Synthesis Example 3-7 [ka]

[1224] Compound A (15 g, 59.4 mmol) and compound amine 3-7 (33.7 g, 62.3 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (24.6 g, 178.1 mmol) dissolved in 74 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred. After filtration, the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 27.9 g of compound 3-7. (Yield 66%, MS: [M+H] + =714)

[1225] Synthesis Example 3-8 [ka]

[1226] Compound A (15 g, 59.4 mmol) and compound amine 3-8 (34 g, 62.3 mmol) were added to 300 mL of THF and stirred under reflux. Potassium carbonate (24.6 g, 178.1 mmol) dissolved in 74 mL of water was then added. After thorough stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 3 hours of reaction, the mixture was cooled to room temperature, the organic and aqueous layers were separated, and the organic layer was distilled. This was then redissolved in chloroform and washed twice with water. The organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stir...

Claims

1. a positive electrode; a negative electrode; and a light-emitting layer between the positive electrode and the negative electrode, The light-emitting layer is formed of at least one compound represented by the following Chemical Formula 1: One or more compounds represented by the following formula 2: Contains one or more compounds represented by the following chemical formula 3: Organic light-emitting devices: 【Chemistry 1】 In the above Chemical Formula 1, Ar １ and Ar ２ are each independently a substituted or unsubstituted aryl having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms containing at least one selected from the group consisting of N, O, and S, L １ ~L ３ each independently represents a single bond; or a substituted or unsubstituted arylene having 6 to 60 carbon atoms, R １ are each independently a substituent selected from the group consisting of deuterium; a substituted or unsubstituted aryl having 6 to 60 carbon atoms; and a substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms containing at least one selected from the group consisting of N, O, and S, a is an integer from 0 to 7, 【Chemistry 2】 In the above Chemical Formula 2, X' １ is N and X' ２ is O; X' １ is O and X' ２ is N, R' １ ~R' ７ is linked to the following Chemical Formula 2A, and the remaining groups are each independently hydrogen; deuterium; a substituted or unsubstituted aryl having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms and containing at least one selected from the group consisting of N, O, and S, 【Transformation 3】 In the chemical formula 2A, L' １ ~L' ３ each independently represents a single bond; or a substituted or unsubstituted arylene having 6 to 60 carbon atoms, Ar' １ and Ar' ２ are each independently a substituted or unsubstituted aryl having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms containing at least one selected from the group consisting of N, O, and S, 【Chemistry 4】 In the above Chemical Formula 3, X" is O or S; R” １ ~R" 5 and R" 8 ~R" １０ is linked to the following Chemical Formula 3A, and the rest are hydrogen or deuterium; 【Transformation 5】 In the above Chemical Formula 3A, L” １ ~L” ３ each independently represents a single bond; or a substituted or unsubstituted arylene having 6 to 60 carbon atoms, Ar” １ and Ar ２ are each independently a substituted or unsubstituted aryl having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms containing at least one selected from the group consisting of N, O, and S.

2. Ar １ and Ar ２ are each independently phenyl, triphenylsilylphenyl, biphenylyl, terphenylyl, naphthyl, phenanthrenyl, chrysenyl, benzo[c]phenanthrenyl, dibenzofuranyl, or dibenzothiophenyl; The Ar １ and Ar ２ are each independently unsubstituted or substituted with one or more deuterium atoms; The organic light-emitting device according to claim 1 .

3. L １ ~L ３ are each independently a single bond, phenylene, biphenyldiyl, naphthalenediyl, phenylnaphthalenediyl, or naphthylnaphthalenediyl, Said L １ ~L ３ is phenylene, biphenyldiyl, naphthalenediyl, phenylnaphthalenediyl, or naphthylnaphthalenediyl, L １ ~L ３ is unsubstituted or substituted with one or more deuterium atoms; The organic light-emitting device according to claim 1 .

4. R １ are each independently hydrogen, deuterium, phenyl, biphenylyl, terphenylyl, naphthyl, phenanthrenyl, triphenylenyl, naphthylphenyl, phenylnaphthyl, fluoranthenyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, or benzonaphthothiophenyl; The R １ is phenyl, biphenylyl, terphenylyl, naphthyl, phenanthrenyl, triphenylenyl, naphthylphenyl, phenylnaphthyl, fluoranthenyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, or benzonaphthothiophenyl; １ are each independently unsubstituted or substituted with one or more deuterium atoms; The organic light-emitting device according to claim 1 .

5. Ar １ , Ar ２ and R １ at least one of is phenyl, naphthyl, phenylnaphthyl, naphthylphenyl, phenanthrenyl, fluoranthenyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, or benzonaphthothiophenyl; The Ar １ , Ar ２ and R １ are each independently unsubstituted or substituted with one or more deuterium atoms; The organic light-emitting device according to claim 1 .

6. The compound represented by Chemical Formula 1 is any one selected from the group consisting of: In the following chemical formula, Dn after parentheses means that n hydrogen atoms in the chemical formula within the parentheses are replaced with deuterium atoms: The organic light-emitting device according to claim 1: 【Transformation 6】 【Transformation 7】 【Transformation 8】 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 【Chemistry 16】 【Chemistry 17】 [Chemistry 18] 【Chemistry 19】 【Chemistry 20】 【Chemistry 21】 【Chemistry 22】 【Chemistry 23】 【Chemistry 24】 【Chemistry 25】 【Chemistry 26】 【Chemistry 27】 【Chemistry 28】 【Chemistry 29】 【Transformation 30】 【Chemistry 31】 【Chemistry 32】 【Transformation 33】 【Transformation 34】 【Chemistry 35】 【Transformation 36】 【Chemistry 37】 【Transformation 38】 【Chemistry 39】 【Chemistry 40】 【Chemistry 41】 【Chemistry 42】 【Chemistry 43】 【Chemistry 44】 【Chemistry 45】 【Chemistry 46】 【Chemistry 47】 【Chemistry 48】 【Chemistry 49】 [Transformation 50] 【Chemistry 51】 【Chemistry 52】 【Chemistry 53】 【Chemistry 54】 【Transformation 55】 【Transformation 56】 【Chemistry 57】 【Transformation 58】 【Chemistry 59】 【Transformation 60】 【Chemistry 61】 【Transformation 62】 【Transformation 63】 【Chemistry 64】 【Transformation 65】 【Chemical Formula 66】 【Transformation 67】 【Transformation 68】 【Transformation 69】 【Transformation 70】 【Chemistry 71】 【Chemistry 72】 【Transformation 73】 【Chemistry 74】 【Chemistry 75】 【Transformation 76】 【Chemical 77】 【Transformation 78】 【Chemistry 79】 【Chemistry 80】 【Chemistry 81】 【Chemistry 82】 【Chemistry 83】 【Chemical 84】 【Chemical 85】 【Chemical 86】 【Chemistry 87】 【Chemical 88】 【Chemical 89】 [Chemical 90] 【Chemistry 91】 【Chemistry 92】 【Chemistry 93】 【Chemical 94】 【Chemical 95】 【Chemistry 96】 【Chemistry 97】 【Chem.98】 【Chem.99】 【Chemistry 100】 【Chemistry 101】 【Chemical Engineering 102】 【Chemistry 103】 【Chemical 104】 【Chemistry 105】 【Chemistry 106】 【Chemistry 107】 【Chemistry 108】 【Chemistry 109】 【Chemical 110】 【Chemistry 111】 【Chemistry 112】 【Chemistry 113】 【Chemistry 114】 【Chemical 115】 【Chemistry 116】 【Chemistry 117】 【Chemistry 118】 【Chemical 119】 【Chemical 120】 【Chemistry 121】 【Chemistry 122】 【Chemical 123】 【Chemistry 124】 【Chemistry 125】 【Chemistry 126】 【Chemistry 127】 【Chemistry 128】 【Chemistry 129】 【Chemistry 130】 【Chemistry 131】 【Chemistry 132】 【Chemistry 133】 【Chemistry 134】 【Chemistry 135】 【Transformation 136】 【Chemistry 137】 【Chemistry 138】 【Chemistry 139】 [Chemical 140] 【Chemistry 141】 【Chemistry 142】 【Chemistry 143】 【Chemistry 144】 【Chemistry 145】 【Chemistry 146】 【Chemistry 147】 【Chemistry 148】 【Chemistry 149】 [Chemical 150] 【Chemistry 151】 【Chemistry 152】 【Chemistry 153】 【Chemistry 154】 【Chemistry 155】 【Chemistry 156】 【Chemistry 157】 【Chemistry 158】 【Chemistry 159】 [Chemical 160] 【Chemistry 161】 【Chemistry 162】 【Chemistry 163】 【Chemistry 164】 【Chemistry 165】 【Chemistry 166】 【Chemistry 167】 【Chemical 168】 【Chemistry 169】 【Chemistry 170】 【Chemistry 171】 【Chemistry 172】 【Chemistry 173】 【Chemistry 174】 【Chemistry 175】 【Chemistry 176】 【Chemistry 177】 【Chemistry 178】 【Chemistry 179】 【Transformation 180】 【Chemistry 181】 【Chemistry 182】 【Chemistry 183】 【Chemistry 184】 【Chemistry 185】 【Chemistry 186】 【Chemistry 187】 【Chemical 188】 【Chemical 189】 【Chemistry 190】 【Chemistry 191】 【Chemistry 192】 【Chemistry 193】 【Chemistry 194】 【Chemistry 195】 【Chemistry 196】 【Chemistry 197】 【Chemistry 198】 【Chemistry 199】 【Chemistry 200】 【Chemical Engineering 201】 【Chemical Engineering 202】 【Chemical 203】 【Chemical 204】 【Chemical 205】 【Chemical 206】 【Chemical 207】 【Chemical 208】 【Chemical Engineering 209】 【Chemical 210】 【Chemistry 211】 【Chemical Engineering 212】 【Chemistry 213】 【Chemical 214】 【Chemical 215】 【Chemical 216】 【Chemical 217】 【Chemical 218】 【Chemical 219】 【Chemical 220】 【Chemistry 221】 【Chemistry 222】 【Chemistry 223】 【Chemistry 224】 【Chemical 225】 【Chemistry 226】 【Chemistry 227】 【Chemistry 228】 【Chemistry 229】 【Chemistry 230】 【Chemistry 231】 【Chemistry 232】 【Chemical 233】 【Chemistry 234】 【Chemical 235】 【Chemistry 236】 【Chemistry 237】 【Chemical 238】 【Chemistry 239】 【Chemistry 240】 【Chemistry 241】 【Chemistry 242】 【Chemistry 243】 【Chemistry 244】 【Chemistry 245】 【Chemistry 246】 【Chemistry 247】 【Chemistry 248】 【Chemistry 249】 [Chemical 250] 【Chemistry 251】 【Chemistry 252】 【Chemistry 253】 【Chemistry 254】 【Chemistry 255】 【Chemistry 256】 【Chemistry 257】 【Chemistry 258】 【Chemistry 259】 【Chemical 260】 【Chemistry 261】 【Chemistry 262】 【Chemical 263】 【Chemistry 264】 【Chemical 265】 【Chemical 266】 【Chemistry 267】 【Chemical 268】 【Chemistry 269】 【Chemistry 270】 【Chemistry 271】 【Chemistry 272】 【Chemistry 273】 【Chemistry 274】 【Chemistry 275】 【Chemistry 276】 【Chemistry 277】 【Chemistry 278】 【Chemistry 279】 【Chemistry 280】 【Chemistry 281】 【Chemistry 282】 【Chemistry 283】 【Chemistry 284】 【Chemical 285】 【Chemistry 286】 。

7. The compound represented by Chemical Formula 2 is represented by either Chemical Formula 2-1 or Chemical Formula 2-2 below: The organic light-emitting device according to claim 1: 【Chemistry 287】 In Chemical Formula 2-1 and Chemical Formula 2-2, R' １ ~R' ６ is hydrogen or deuterium, R' ７ is a substituted or unsubstituted aryl having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms containing at least one selected from the group consisting of N, O, and S, X' １ , X' ２ , L' １ ~L' ３ , Ar' １ and Ar' ２ is as defined in claim 1.

8. R' １ ~R' ７ is Formula 2A, and the remaining groups are each independently hydrogen, deuterium, phenyl, biphenylyl, or naphthyl; the phenyl, biphenylyl, and naphthyl are each independently unsubstituted or substituted with one or more deuterium atoms; The organic light-emitting device according to claim 1 .

9. L' １ ~L' ３ each independently represents a single bond, phenylene, biphenyldiyl, terphenyldiyl, naphthalenediyl, or phenylnaphthalenediyl; the phenylene, biphenyldiyl, terphenyldiyl, naphthalenediyl, and phenylnaphthalenediyl are each independently unsubstituted or substituted with one or more deuterium atoms; The organic light-emitting device according to claim 1 .

10. Ar' １ and Ar' ２ are each independently phenyl, biphenylyl, terphenylyl, naphthyl, phenylnaphthyl, phenanthrenyl, dimethylfluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, or phenylcarbazolyl; The Ar′ １ and Ar' ２ is unsubstituted or substituted with one or more deuterium atoms; The organic light-emitting device according to claim 1 .

11. The compound represented by Chemical Formula 2 is any one selected from the group consisting of: The organic light-emitting device according to claim 1: 【Chemical 288】 【Chemistry 289】 【Chemistry 290】 【Chemistry 291】 【Chemistry 292】 【Chemistry 293】 【Chemistry 294】 【Chemistry 295】 【Chemistry 296】 【Chemistry 297】 【Chemistry 298】 【Chemistry 299】 [Chemical 300] 【Chemical 301】 【Chemical 302】 【Chemical 303】 【Chemical 304】 【Chemical 305】 【Chemical 306】 【Chemical 307】 【Chemical 308】 【Chemical 309】 【Chemical 310】 【Chemical 311】 【Chemical 312】 【Chemistry 313】 【Chemical 314】 【Chemical Industry 315】 【Chemical 316】 【Chemical 317】 【Chemical 318】 【Chemical 319】 【Chem.320】 【Chemistry 321】 【Chemistry 322】 【Chemical 323】 【Chemical 324】 【Chemical 325】 【Chemistry 326】 【Chemistry 327】 【Chemical 328】 【Chemistry 329】 【Chemistry 330】 【Chemistry 331】 【Chemistry 332】 【Chemical 333】 【Chemistry 334】 【Chemistry 335】 【Chemistry 336】 【Chemistry 337】 【Chemical 338】 【Chemistry 339】 【Chemistry 340】 【Chemistry 341】 【Chemistry 342】 【Transformation 343】 【Transformation 344】 【Chemistry 345】 【Transformation 346】 【Transformation 347】 【Transformation 348】 【Chemistry 349】 [Chemical 350] 【Chemistry 351】 【Chemistry 352】 【Chemistry 353】 【Chemistry 354】 【Chemical 355】 【Transformation 356】 【Chemistry 357】 【Chemical 358】 【Chemistry 359】 【Chemical 360】 【Chemical 361】 【Chemical 362】 【Chemical 363】 【Chemical 364】 【Chemical 365】 【Chemical 366】 【Chemical 367】 【Chemical 368】 【Chemical 369】 【Chemistry 370】 【Chemistry 371】 【Chemistry 372】 【Chemistry 373】 【Chemistry 374】 【Chemistry 375】 【Transformation 376】 【Chemical 377】 【Chemistry 378】 【Chemistry 379】 【Chemical 380】 【Chemistry 381】 【Chem.382】 【Chemistry 383】 【Chemical 384】 【Chem.385】 【Chemical 386】 【Chemistry 387】 【Chemical 388】 【Chemistry 389】 【Chemical 390】 【Chemistry 391】 【Chemistry 392】 【Chemistry 393】 【Chem. 394】 【Chemical 395】 【Chemistry 396】 【Chemistry 397】 【Chem.398】 【Chem.399】 【Chemical 400】 【Chemical 401】 【Chemical 402】 【Chemical 403】 【Chemical 404】 【Chemical 405】 【Chemical 406】 【Chemical 407】 【Chemical 408】 【Chemical 409】 【Chemical 410】 【Chemical 411】 【Chemical 412】 【Chemical 413】 【Chemical 414】 【Chemical 415】 【Chemical 416】 【Chemical 417】 【Chemical 418】 【Chemical 419】 。

12. The formula 3A is R" of the formula 3. １ , R” ２ , R” ４ , R” ５ and R” ８ ~R” １０ Concatenated with one of The organic light-emitting device according to claim 1 .

13. L” １ ~L” ３ each independently represents a single bond, phenylene, biphenyldiyl, naphthalenediyl, or dimethylfluorenediyl; the phenylene, biphenyldiyl, naphthalenediyl, and dimethylfluorenediyl are each independently unsubstituted or substituted with one or more deuterium atoms; The organic light-emitting device according to claim 1 .

14. Ar” １ and Ar ２ are each independently phenyl, triphenylsilylphenyl, biphenylyl, terphenylyl, naphthyl, phenanthrenyl, dimethylfluorenyl, spirobifluorenyl, dibenzofuranyl, dibenzothiophenyl, or phenylcarbazolyl; The Ar" １ and Ar ２ are each independently unsubstituted or substituted with one or more deuterium atoms; The organic light-emitting device according to claim 1 .

15. The compound represented by Chemical Formula 3 is any one selected from the group consisting of: In the following chemical formula, Dn after parentheses means that n hydrogen atoms in the chemical formula within the parentheses are replaced with deuterium atoms: The organic light-emitting device according to claim 1: 【Chem.420】 【Chemistry 421】 【Chemistry 422】 【Chemistry 423】 【Chemistry 424】 【Chemical 425】 【Chemistry 426】 【Chemistry 427】 【Chemistry 428】 【Chemistry 429】 【Chemistry 430】 【Chemistry 431】 【Chemistry 432】 【Chemistry 433】 【Chemistry 434】 【Chemical 435】 【Chemistry 436】 【Chemistry 437】 【Chemistry 438】 【Chemistry 439】 【Chemical 440】 【Chemistry 441】 【Chemistry 442】 【Chemistry 443】 【Chemistry 444】 【Chemistry 445】 【Chemistry 446】 【Chemistry 447】 【Chemistry 448】 【Chemistry 449】 [Chemical 450] 【Chemistry 451】 【Chemistry 452】 【Chemistry 453】 【Chemical 454】 【Chemistry 455】 【Chemistry 456】 【Chemistry 457】 【Chemistry 458】 【Chemistry 459】 【Chemical 460】 【Chemistry 461】 【Chemistry 462】 【Chemical 463】 【Chemical 464】 【Chemical 465】 【Chemical Formula 466】 【Chemistry 467】 【Chemical 468】 【Chemistry 469】 【Chemical 470】 【Chemistry 471】 【Chemistry 472】 【Chemistry 473】 【Chemistry 474】 【Chemistry 475】 【Chemistry 476】 【Chemistry 477】 【Chemistry 478】 【Chemistry 479】 【Chemical 480】 【Chemistry 481】 【Chemistry 482】 【Chemistry 483】 【Chem.484】 【Chemistry 485】 【Chemical 486】 【Chemistry 487】 【Chemical 488】 【Chemistry 489】 【Chemistry 490】 【Chemistry 491】 【Chemistry 492】 【Chemistry 493】 【Chem.494】 【Chemical 495】 【Chemistry 496】 【Chemistry 497】 【Chem.498】 【Chem.499】 [500] 【Chemical 501】 【Chemical 502】 【Chemical 503】 【Chemical 504】 【Chemical 505】 【Chemical 506】 【Chemical 507】 【Chemical 508】 【Chemical 509】 【Chemical 510】 【Chemical 511】 【Chemical 512】 【Chemical 513】 【Chemical 514】 【Chemical Formula 515】 【Chemical Formula 516】 【Chemical 517】 【Chemical 518】 【Chemical 519】 【Chemical 520】 【Chem.521】 【Chemical Formula 522】 【Chemical Formula 523】 【Chemical 524】 【Chemical 525】 【Chemical 526】 【Chemical 527】 【Chemical Formula 528】 【Chemical 529】 【Chemical 530】 【Chemistry 531】 【Chemical 532】 【Chemical 533】 【Chemistry 534】 【Chemical 535】 【Chemical 536】 【Chemical 537】 【Chemical 538】 【Chemical Formula 539】 【Chemical 540】 【Chemistry 541】 【Chemistry 542】 【Chemistry 543】 【Chemical 544】 【Chemical 545】 【Chemical Formula 546】 【Chemistry 547】 【Chemical 548】 【Chemistry 549】 【Chemical 550】 【Chemistry 551】 【Chemical Formula 552】 【Chemical 553】 【Chemical Formula 554】 【Chemical 555】 【Chemical Formula 556】 【Chemical 557】 【Chemical Formula 558】 【Chemical Formula 559】 【Chemical 560】 【Chemical 561】 【Chemical Formula 562】 【Chemical 563】 【Chemical Formula 564】 【Chemical 565】 【Chemical 566】 【Chemical 567】 【Chemical 568】 【Chemical 569】 【Chemical 570】 【Chemistry 571】 【Chemistry 572】 【Chemistry 573】 【Chemistry 574】 【Chemical 575】 【Chemical 576】 【Chemical 577】 【Chemical 578】 【Chemistry 579】 【Chemical 580】 【Chemistry 581】 【Chemical 582】 【Chemical 583】 【Chemical 584】 【Chemical 585】 【Chemical 586】 【Chemical 587】 【Chemical 588】 【Chemical 589】 【Chemical 590】 【Chemistry 591】 【Chem.592】 【Chem.593】 【Chem.594】 【Chemical Formula 595】 【Chemical Formula 596】 【Chemistry 597】 【Chemical Formula 598】 【Chemical Formula 599】 【Chemical 600】 【Chemical 601】 【Chemical 602】 【Chemical 603】 【Chemical 604】 【Chemical 605】 【Chemical 606】 【Chemical 607】 【Chemical 608】 【Chemical 609】 【Chemical 610】 【Chemical 611】 【Chemical 612】 【Chemical 613】 【Chemical 614】 【Chemical Formula 615】 【Chemical Formula 616】 【Chemical 617】 【Chemical 618】 【Chemical 619】 【Chemical Formula 620】 【Chemical 621】 【Chemical Formula 622】 【Chemical Formula 623】 【Chemical Formula 624】 【Chemical 625】 【Chemical 626】 【Chemical Formula 627】 【Chemical Formula 628】 【Chemical Formula 629】 【Chemical 630】 【Chemistry 631】 【Chemical 632】 【Chemical 633】 【Transformation 634】 【Chemical 635】 【Chemical Formula 636】 【Chemical Formula 637】 【Chemical 638】 【Chemistry 639】 【Chemical 640】 【Chemistry 641】 【Chemistry 642】 【Chemistry 643】 【Chemical Formula 644】 【Chemistry 645】 【Chemical Formula 646】 【Chemical Formula 647】 【Chemical Formula 648】 【Chemical 649】 【Chemical 650】 【Chemical 651】 【Chemical 652】 【Chemical 653】 。

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