Method for synthesizing fluorine-containing 3-hydroxyindole-2-ketone compound
Synthesis of fluorine-containing 3-hydroxyindole-2-one compounds by photocatalysts and alkalis under blue light, the problems of high demand for transition metals and limited substrate range in the prior art are solved, and a green and efficient synthesis method is achieved.
Patent Information
- Application Number
- CN202510241987.4
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2025-03-03
- Publication Date
- 2025-07-04
AI Technical Summary
The prior art has problems such as high transition metal demand, strict reaction conditions and limited substrate range when synthesizing 3-hydroxyindole-2-one compounds, and lacks green and efficient synthesis methods.
Under blue light irradiation, the photocatalyst and its derivatives are reacted with the bromodifluoroacetate compound in a specific solvent, and the fluorine-containing 3-hydroxyindole-2-one compound is synthesized through the free radical pathway, avoiding the participation of transition metals.
It has achieved the synthesis of fluorine-containing 3-hydroxyindole-2-one compounds without transition metal participation, wide application range of substrates, mild reaction conditions, and efficient synthesis of fluorine-containing 3-hydroxyindole-2-one compounds, which are simple to operate and environmentally friendly.
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Figure QLYQS_1 
Figure QLYQS_2 
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Abstract
Description
Technical Field
[0001] The present invention relates to the technical field of photocatalytic synthesis, and particularly relates to a method for synthesizing fluorine-containing 3-hydroxyindol-2-one compounds. Background Art
[0002] 3-Hydroxyindol-2-one compounds widely exist in many natural products and drug molecules, have antioxidant and anticancer activities, and have wide applications in the field of medicinal chemistry. In addition, introducing fluorine atoms into organic molecules is an important direction for developing new antitumor drugs, antiviral and anti-inflammatory drugs, etc. In modern crop protection, fluorine-containing agrochemicals are also widely used as herbicides, insecticides, and fungicides, etc. Therefore, synthesizing fluorine-containing 3-hydroxyindol-2-one compounds has important significance. At present, the synthesis of 3-hydroxyindol-2-one compounds using transition metal catalysis or using alcohols as raw materials under high temperature conditions has been reported. Although these methods have successfully constructed 3-hydroxyindol-2-one compounds, they still face problems such as the need for transition metals, substrate preparation, strict reaction conditions, and limited substrate scope. Therefore, it is still necessary to develop green and efficient methods to construct such compounds.
[0003] In recent years, light, as a green and efficient energy source, has attracted the attention of chemists. Therefore, it is of great significance to develop a simple and green method using photocatalysis to synthesize target compounds under mild conditions. Summary of the Invention
[0004] The present invention provides a green method for preparing fluorine-containing 3-hydroxyindol-2-one compounds, which has the advantages of no participation of transition metals, wide substrate scope, and high efficiency. In addition, this method can synthesize the target compound under mild, simple, and efficient reaction conditions.
[0005] To achieve the object of the present invention, the present invention provides the following technical solutions.
[0006] A method for synthesizing fluorine-containing 3-hydroxyindol-2-one compounds is to react a compound of formula I and a compound of formula II in a solvent under a photocatalyst, a base, and blue light irradiation to obtain a compound of formula III;
[0007] The specific reaction formula is as follows:
[0008]
[0009] Wherein, R 1 、R 2 、R 3 、R 4 、R 5Each independently selected from hydrogen, alkyl, cycloalkyl, aryl, heteroaryl, halogen, methoxy, nitro, cyano, ester group; wherein, the alkyl, cycloalkyl, aryl and heteroaryl are each independently unsubstituted or substituted by a substituent.
[0010] Wherein, the alkyl is a C1-C40 alkyl; the cycloalkyl is a C3-C40 cycloalkyl; the aryl is a C6-C18 aryl; the heteroaryl is a C5-C18 heteroaryl containing 1-3 heteroatoms, wherein the heteroatoms are one or more of oxygen atoms, sulfur atoms and nitrogen atoms.
[0011] Wherein, the structural formula of the compound of formula III is as follows:
[0012]
[0013] Wherein, a magnetic stir bar is added to a pre-dried 4 mL sample bottle, compound I, a photocatalyst and a base are added, nitrogen is evacuated and replaced, a solvent is injected under nitrogen protection, compound II is added using a microsyringe, irradiated with blue light and stirred until thin layer chromatography shows that starting material I has disappeared, the reaction solution is concentrated, and the compound shown in III is obtained after separation and purification by column chromatography.
[0014] Wherein, a method for synthesizing a fluorine-containing 3-hydroxyindole-2-one compound specifically comprises the following steps:
[0015] The photocatalyst is selected from at least one of [Ir(dF(CF3ppy)2(dtbbpy)][PF6], [Ir(ppy)2(dtbbpy)][PF6],
[0016] [Ir(dF(CF3ppy)2(5,5’-d(CF3)bpy)][PF6], [Ir(dF(CF3ppy)2(bpy)][PF6],
[0017] [Ir(dF(Me)ppy)2(dtbbpy)][PF6], [Ir(ppy)3], [Ir(dFppy)3], [Ir(4-Fppy)3], DCB, DCA, Mes-Acr + , Eosin Y, [Ru(bpy)3] 2+ , [Ru(bpm)3] 2+ , [Ru(bpz)3] 2+ , Rose Bengal, Benzophenone, 4CZIPN, [Ru(phen)3] 2+ ;
[0018] The base is selected from at least one of 1,8-diazabicyclo[5.4.0]undec-7-ene, 1,4-diazabicyclo[2.2.2]octane, triethylamine, diethylamine, N,N-diisopropylethylamine, potassium phosphate, potassium hydrogen phosphate, potassium acetate, cesium carbonate, cesium acetate, potassium carbonate, potassium bicarbonate, sodium carbonate, sodium bicarbonate, and sodium methoxide;
[0019] The solvent is selected from at least one of benzene, toluene, xylene, chlorobenzene, fluorobenzene, trifluorotoluene, 1,4-dioxane, tetrahydrofuran, diethyl ether, chloroform, dichloromethane, 1,2-dichloroethane, ethyl acetate, acetone, acetonitrile, N,N-dimethylformamide, N,N-dimethylacetamide, and dimethyl sulfoxide;
[0020] Among them, the molar ratio of the compound I to the compound II is 1:1 - 1:2
[0021] Among them, the molar ratio of the isatin and its derivatives to the catalyst is 1:0.001 - 1:0.005.
[0022] Among them, the molar ratio of the compound I to the base is 1:1 - 1:2.
[0023] Among them, the reaction temperature is 10 - 40 °C; the reaction time is more than 6 h.
[0024] Compared with the prior art, the present invention has the following beneficial effects:
[0025] The present invention uses photocatalysis to develop a green method for synthesizing fluorine-containing 3-hydroxyindole-2-one compounds with mild reaction conditions; it has the advantages of no participation of transition metals, wide substrate scope, and high efficiency. In addition, this method can synthesize the target compound under mild, simple, and efficient reaction conditions. Specific Embodiments
[0026] The following will clearly and completely describe the technical solutions of the present invention in conjunction with specific embodiments of the present invention. Obviously, the described embodiments are only a part of the embodiments of the present invention, rather than all of the embodiments. Based on the embodiments in the present invention, all other embodiments obtained by those of ordinary skill in the art without creative efforts fall within the protection scope of the present invention.
[0027] The materials used in the following embodiments can be obtained from public commercial channels without special instructions. The nuclear magnetic resonance spectra were measured by a Bruker nuclear magnetic resonance spectrometer.
[0028] The synthesis route for all the following embodiments of the present invention is:
[0029]
[0030] Example 1
[0031] This example provides a method for synthesizing a fluorine-containing 3-hydroxyindole-2-one compound (3a), which includes the following steps:
[0032] A magnetic stir bar is added to a pre-dried 4 mL sample vial, and isatin (R 1 、R 2 、R 3 、R 4 = hydrogen (abbreviated as H) (0.2 mmol, 1 equivalent), photocatalyst ([Ir(ppy)2(dtbbpy)][PF6], 0.006 mmol, 0.003 equivalent), Cs2CO3 (0.4 mmol, 2.0 equivalents) are added. The vial is evacuated and backfilled with nitrogen three times, and then 2 mL of acetonitrile is injected under nitrogen protection. Methyl bromodifluoroacetate II (R 5 = methyl (abbreviated as Me) (0.4 mmol, 2 equivalents)) is added using a microsyringe, and the mixture is irradiated with blue light and stirred. The reaction temperature is 20 °C until thin-layer chromatography shows that the raw material I has disappeared. The reaction solution is concentrated, and the compound shown in III is obtained after separation and purification by column chromatography. The obtained target product is a colorless oily liquid with a yield of 75%.
[0033]
[0034] The experimental data of 3a are as follows:
[0035] 1 H NMR (500 MHz, CDCl3): δ 10.01 (s, 1H), 7.07 (t, 1H), 6.66 - 6.61 (m, 2H), 6.07 (d, J = 7.4 Hz, 1H), 5.90 (s, 1H), 3.75 (s, 3H). 13 C NMR (125 MHz, CDCl3) δ 179.5, 161.7, 144.8, 131.1 (q, J CF = 288.5 Hz), 128.4, 127.3, 126.6, 126.0, 102.2, 51.9.
[0036] Example 2
[0037] This example provides a method for synthesizing a fluorine-containing 3-hydroxyindole-2-one compound (3b), which includes the following steps:
[0038] A magnetic stir bar is added to a pre-dried 4 mL sample vial, and compound I (R 2 、R 3 、R 4 = hydrogen (abbreviated as H), R 1=CH3 (0.2 mmol, 1 equivalent), photocatalyst (Eosin Y (0.002 mmol, 0.001 equivalent), 1,8-diazabicyclo[5.4.0]undec-7-ene (0.2 mmol, 1.0 equivalent), nitrogen was evacuated and replaced three times, and 2 mL of chlorobenzene was injected under nitrogen protection. Methyl bromodifluoroacetate II (R 5 = methyl (abbreviated as Me) (0.3 mmol, 1.5 equivalents)) was added with a microsyringe, irradiated with blue light and stirred. The reaction temperature was 10 °C until thin-layer chromatography showed that starting material I disappeared. The reaction solution was concentrated, and the compound shown in III was obtained after purification by column chromatography. The obtained target product was a colorless oily liquid with a yield of 78%.
[0039]
[0040] The experimental data of 3b are as follows:
[0041] 1 1H NMR (500 MHz, CDCl3): δ 9.84 (s, 1H), 6.97 (t, J = 7.7 Hz, 1H), 6.50 (d, J = 7.7 Hz, 1H), 6.40 (d, J = 7.6 Hz, 1H), 5.90 (s, 1H), 3.78 (s, 3H) 1.42 (s, 3H). 13 13C NMR (125 MHz, CDCl3) δ 180.1, 166.5, 145.6, 137.4, (q, J CF = 288.7 Hz), 128.4, 127.3, 126.6, 126.0, 102.2, 51.9, 17.5.
[0042] Example 3
[0043] This example provides a method for synthesizing a fluorine-containing 3-hydroxyindole-2-one compound (3c), which includes the following steps:
[0044] A magnetic stir bar was added to a pre-dried 4 mL sample bottle, and compound I (R 2 , R 3 , R 4 = hydrogen (abbreviated as H), R 1 = OMe (0.2 mmol, 1 equivalent), photocatalyst ([Ru(bpm)3] 2+ , (0.01 mmol, 0.005 equivalent), triethylamine (0.4 mmol, 2.0 equivalents), nitrogen was evacuated and replaced three times, and 2 mL of ethyl acetate was injected under nitrogen protection. Methyl bromodifluoroacetate II (R 5Methyl (abbreviated as Me) (0.3 mmol, 1.5 equiv), irradiated with blue light and stirred, reaction temperature 40 °C until thin-layer chromatography control showed disappearance of starting material I. The reaction solution was concentrated and purified by column chromatography to obtain the compound shown in III. The obtained target product was a colorless oily liquid with a yield of 79%.
[0045]
[0046] The experimental data of 3c are as follows:
[0047] 1 1H NMR (500 MHz, CDCl3): δ 9.90 (s, 1H), 7.45 (d, J = 7.3 Hz, 1H), 7.02 (s, 1H), 6.55 (d, J = 8.3 Hz, 1H), 5.92 (s, 1H), 5.85 (s, 1H), 3.70 (s, 3H), 3.64 (s, 3H). 13 13C NMR (125 MHz, CDCl3) δ 179.4, 164.5 (q, J CF = 288.4 Hz), 154.0, 136.0, 132.3, 128.6, 114.3, 112.8, 111.9, 55.9, 52.1.
[0048] Example 4
[0049] This example provides a method for synthesizing a fluorine-containing 3-hydroxyindol-2-one compound (3d), comprising the following steps:
[0050] A magnetic stir bar was added to a pre-dried 4 mL sample vial, and compound I (R 2 、R 3 、R 4 = hydrogen (abbreviated as H), R 1 = Cl (0.2 mmol, 1 equiv), photocatalyst (Rose Bengal, 0.006 mmol, 0.003 equiv), sodium methoxide (0.4 mmol, 2.0 equiv) were added. The vial was evacuated and filled with nitrogen three times, and 2 mL of dimethyl sulfoxide was injected under nitrogen protection. Methyl bromodifluoroacetate II (R 5 = methyl (abbreviated as Me) (0.3 mmol, 1.5 equiv)) was added using a microsyringe. The mixture was irradiated with blue light and stirred at 30 °C until thin-layer chromatography control showed disappearance of starting material I. The reaction solution was concentrated and purified by column chromatography to obtain the compound shown in III. The obtained target product was a colorless oily liquid with a yield of 74%.
[0051]
[0052] The experimental data of 3d are as follows:
[0053] 1 1H NMR (500 MHz, CDCl3) δ 10.64 (s, 1H), 7.60 (d, J = 8.2 Hz, 1H), 7.19 - 7.20 (m, 1H), 7.01 (d, J = 7.4 Hz, 1H), 6.11 (s, 1H), 3.65 (s, 3H). 13 13C NMR (125 MHz, CDCl3) δ 179.4, 164.0 (q, J CF = 288.4 Hz), 144.4, 132.3, 129.3, 128.6, 124.3, 112.8, 101.9, 51.9.
[0054] Example 5
[0055] This example provides a method for synthesizing a fluorine-containing 3-hydroxyindol-2-one compound (3e), which includes the following steps:
[0056] A magnetic stir bar was added to a pre-dried 4 mL sample vial, and compound I (R 2 、R 3 、R 4 = hydrogen (abbreviated as H), R 1 = Cl (0.2 mmol, 1 equivalent), photocatalyst (Rose Bengal, 0.006 mmol, 0.003 equivalent), sodium methoxide (0.4 mmol, 2.0 equivalents) were added. The mixture was evacuated and backfilled with nitrogen three times, and then 2 mL of dimethyl sulfoxide was injected under nitrogen protection. Methyl bromodifluoroacetate II (R 5 = methyl (abbreviated as Me) (0.3 mmol, 1.5 equivalents)) was added using a microsyringe. The mixture was irradiated with blue light and stirred at 30 °C until the disappearance of starting material I was shown by thin-layer chromatography. The reaction solution was concentrated, and the compound shown in III was obtained after separation and purification by column chromatography. The obtained target product was a colorless oily liquid with a yield of 77%.
[0057]
[0058] The experimental data of 3e are as follows:
[0059] 1 1H NMR (500 MHz, CDCl3) δ 10.40 (s, 1H), 7.41 (d, J = 8.2 Hz, 1H), 7.33 (d, J = 7.6 Hz, 1H), 6.93 (d, J = 7.4 Hz, 1H), 6.08 (s, 1H), 3.65 (s, 3H), 2.26 (s, 3H). 13 13C NMR (125 MHz, CDCl3) δ 179.8, 164.0 (q, J CF= 288.4 Hz), 141.4, 137.3, 129.7, 125.6, 124.3, 112.8, 101.9, 51.9, 21.3.
[0060] Example 6
[0061] This example provides a method for synthesizing a fluorine-containing 3-hydroxyindole-2-one compound (3f), which includes the following steps:
[0062] Add a magnetic stir bar to a pre-dried 4 mL sample vial, and add compound I (R 2 、R 3 、R 4 = hydrogen (abbreviated as H), R 1 = Cl (0.2 mmol, 1 equivalent), photocatalyst (Benzophenone, 0.006 mmol, 0.003 equivalent), sodium methoxide (0.4 mmol, 2.0 equivalents), evacuate and refill with nitrogen 3 times, inject 2 mL of dimethyl sulfoxide under nitrogen protection, add methyl bromodifluoroacetate II (R 5 = methyl (abbreviated as Me) (0.3 mmol, 1.5 equivalents)) using a microsyringe, irradiate with blue light and stir, the reaction temperature is 30 °C until thin-layer chromatography shows that starting material I has disappeared, concentrate the reaction solution, and obtain the compound shown in III after column chromatography separation and purification. The obtained target product is a colorless oily liquid with a yield of 70%.
[0063]
[0064] The experimental data of 3f are as follows:
[0065] 1 H NMR (500 MHz, CDCl3) δ 10.64 (s, 1H), 7.60 - 7.04 (m, 3H), 6.06 (s, 1H), 3.65 (s, 3H). 13 C NMR (125 MHz, CDCl3) δ 179.9, 164.0 (q, J CF = 288.4 Hz), 143.8, 132.8, 129.3, 128.6, 126.2, 124.3, 102.0, 51.9.
[0066] Example 7
[0067] This example provides a method for synthesizing a fluorine-containing 3-hydroxyindole-2-one compound (3g), which includes the following steps:
[0068] Add a magnetic stir bar to a pre-dried 4 mL sample vial, and add compound I (R 2 、R 3 、R 4= hydrogen (abbreviated as H), R 1 = Cl (0.2 mmol, 1 equivalent), photocatalyst (4CZIPN, 0.006 mmol, 0.003 equivalent), sodium methoxide (0.4 mmol, 2.0 equivalents), nitrogen was evacuated and replaced three times, and 2 mL of dimethyl sulfoxide was injected under nitrogen protection. Methyl bromodifluoroacetate II (R 5 = methyl (abbreviated as Me) (0.3 mmol, 1.5 equivalents)) was added with a microsyringe, irradiated and stirred with blue light, and the reaction temperature was 30 °C until thin-layer chromatography showed that starting material I disappeared. The reaction solution was concentrated, and the compound shown in III was obtained after purification by column chromatography. The obtained target product was a colorless oily liquid with a yield of 73%.
[0069]
[0070] The experimental data of 3 g are as follows:
[0071] 1 H NMR (500 MHz, CDCl3) δ 10.40 (s, 1H), 8.05 (s, 1H), 7.85 - 7.80 (m, 2H), 6.08 (s, 1H), 3.89 (s, 3H), 3.65 (s, 3H). 13 C NMR (125 MHz, CDCl3) δ 179.8, 164.0 (q, J CF = 288.4 Hz), 146.7, 132.8, 129.0, 127.8, 126.2, 109.8, 101.9, 51.9, 51.5.
[0072] Example 8
[0073] This example provides a method for synthesizing a fluorine-containing 3-hydroxyindol-2-one compound (3h), which includes the following steps:
[0074] A magnetic stir bar was added to a pre-dried 4 mL sample bottle, and compound I (R 2 、R 3 、R 4 = hydrogen (abbreviated as H), R 1 = Cl (0.2 mmol, 1 equivalent), photocatalyst (Mes-Acr + , 0.006 mmol, 0.003 equivalent), sodium methoxide (0.4 mmol, 2.0 equivalents), nitrogen was evacuated and replaced three times, and 2 mL of dimethyl sulfoxide was injected under nitrogen protection. Methyl bromodifluoroacetate II (R 5Methyl (abbreviated as Me) (0.3 mmol, 1.5 equiv)) was irradiated with blue light while stirring. The reaction temperature was 30 °C until thin-layer chromatography showed the disappearance of starting material I. The reaction solution was concentrated and purified by column chromatography to obtain the compound shown in III. The obtained target product was a colorless oily liquid with a yield of 80%.
[0075]
[0076] The experimental data for 3 h are as follows:
[0077] 1 H NMR (500 MHz, CDCl3) δ 10.64 (s, 1H), 7.60 (d, J = 8.2 Hz, 1H), 7.19 - 7.20 (m, 1H), 7.01 (d, J = 7.4 Hz, 1H), 6.11 (s, 1H), 3.65 (s, 3H). 13 C NMR (125 MHz, CDCl3) δ 179.8, 164.0 (q, J CF = 288.4 Hz), 138.3, 134.7, 130.0, 129.3, 128.6, 124.3, 103.9, 51.9, 21.9, 17.6.
[0078] The above are only the preferred embodiments of the present invention and are not used to limit the present invention. For those skilled in the art, the present invention can have various modifications and changes. Any modifications, equivalent replacements, improvements, etc. made within the spirit and principle of the present invention shall be included within the protection scope of the present invention.
Claims
1. A method for synthesizing a fluorine-containing 3-hydroxyindol-2-one compound, characterized in that: Under the irradiation of a photocatalyst, a base and blue light, the compound of formula I and the compound of formula II are reacted in a solvent to obtain the compound of formula III; The specific reaction formula is as follows: Among them, R 1 , R 2 , R 3 , R 4 , R 5 are each independently selected from hydrogen, alkyl, cycloalkyl, aryl, heteroaryl, halogen, methoxy, nitro, cyano, ester group; wherein, the alkyl, cycloalkyl, aryl and heteroaryl are each independently unsubstituted or substituted by a substituent.
2. The method for synthesizing a fluorine-containing 3-hydroxyindole-2-one compound according to claim 1, characterized in that: The alkyl group is a C1-C40 alkyl group; the cycloalkyl group is a C3-C40 cycloalkyl group; the aryl group is a C6-C18 aryl group; the heteroaryl group is a C5-C18 heteroaryl group containing 1-3 heteroatoms, wherein the heteroatoms are one or more of an oxygen atom, a sulfur atom and a nitrogen atom.
3. The method for synthesizing a fluorine-containing 3-hydroxyindole-2-one compound according to claim 1, wherein The structural formula of the compound of formula III is as follows:
4. The method for synthesizing a fluorine-containing 3-hydroxyindole-2-one compound according to claim 1, wherein Specifically, the following steps are included: adding a magnetic stir bar into a pre-dried 4 mL sample bottle, adding Compound I, a photocatalyst and a base, evacuating and replacing with nitrogen, injecting a solvent under nitrogen protection, adding Compound II with a micro syringe, irradiating with blue light and stirring until thin layer chromatography shows that starting material I disappears, concentrating the reaction solution, and purifying by column chromatography to obtain the compound shown in III.
5. The method for synthesizing a fluorine-containing 3-hydroxyindole-2-one compound according to claim 1, wherein Specifically, the following steps are included: The photocatalyst is selected from [Ir(dF(CF3ppy)2(dtbbpy)][PF6], [Ir(ppy)2(dtbbpy)][PF6], [Ir(dF(CF3ppy)2(5,5’-d(CF3)bpy)][PF6], [Ir(dF(CF3ppy)2(bpy)][PF6], [Ir(dF(Me)ppy)2(dtbbpy)][PF6], [Ir(ppy)3], [Ir(dFppy)3], [Ir(4-Fppy)3], DCB, DCA, Mes-Acr + , Eosin Y, [Ru(bpy)3] 2+ , [Ru(bpm)3] 2+ , [Ru(bpz)3] 2+ , Rose Bengal, Benzophenone, 4CZIPN, [Ru(phen)3] 2+ ; and at least one of them The base is selected from at least one of 1,8-diazabicyclo[5.4.0]undec-7-ene, 1,4-diazabicyclo[2.2.2]octane, triethylamine, diethylamine, N,N-diisopropylethylamine, potassium phosphate, potassium hydrogen phosphate, potassium acetate, cesium carbonate, cesium acetate, potassium carbonate, potassium bicarbonate, sodium carbonate, sodium bicarbonate, sodium methoxide; The solvent is selected from at least one of benzene, toluene, xylene, chlorobenzene, fluorobenzene, trifluorotoluene, 1,4-dioxane, tetrahydrofuran, diethyl ether, chloroform, dichloromethane, 1,2-dichloroethane, ethyl acetate, acetone, acetonitrile, N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide; 6. The method for synthesizing a fluorine-containing 3-hydroxyindole-2-one compound according to claim 1, wherein: The molar ratio of Compound I to Compound II is 1:1 - 1:
2.
7. The method for synthesizing a fluorine-containing 3-hydroxyindol-2-one compound according to claim 1, characterized in that: The molar ratio of the isatin and its derivatives to the catalyst is 1:0.001 - 1:0.
005.
8. The method for synthesizing a fluorine-containing 3-hydroxyindole-2-one compound according to claim 1, characterized in that: The molar ratio of Compound I to the base is 1:1 - 1:
2.
9. The method for synthesizing a fluorine-containing 3-hydroxyindole-2-one compound according to claim 1, characterized in that: The reaction temperature is 10 - 40 °C; the reaction time is more than 6 h.