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A kind of method for preparing indolopyrrolone compound

A technology for indolopyrrolone and indole compounds, which is applied in the field of organic chemical synthesis, can solve the problem of low yield, and achieve the effects of wide substituent compatibility and high reaction yield

Active Publication Date: 2020-05-19
INST OF CHEM CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0003] The preparation methods of indolopyrrolone compounds in the prior art mainly include: the following methods are disclosed in J.Org.Chem.2017,82,5263-5273: (such as figure 1 shown); it uses a ruthenium catalyst to catalyze the reaction of indole and alkyne to produce indolopyrrole compounds, but the R' substituent in the substrate alkyne used is mainly methyl, although there are also examples of R' being aryl , but the corresponding yield is not high ( figure 2 shown), which uses a cobalt catalyst to catalyze the reaction of indole and alkyne to produce indolopyrrole compounds, but the R' substituent in the substrate alkyne is mainly methyl, although there are also examples where R' is an aryl group , but the corresponding yield is not high ( image 3 shown), there is only one reaction involving indole ( Figure 4 shown), and the yield was low (39%)

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  • A kind of method for preparing indolopyrrolone compound
  • A kind of method for preparing indolopyrrolone compound
  • A kind of method for preparing indolopyrrolone compound

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preparation example Construction

[0049] According to one embodiment of the present invention, a preparation method of an indolopyrrolone compound is disclosed, the preparation method comprising the following steps:

[0050] In the presence of catalysts, Lewis acids and zinc reagents, the indole compound shown in formula II and the alkyne shown in formula III undergo a C-H bond activation / C-N bond cleavage reaction to obtain the indolopyrrole compound shown in formula I. Ketone compounds;

[0051]

[0052] in,

[0053] R 1 independently represent mono-substitution, di-substitution, tri-substitution, tetra-substitution or no substitution;

[0054] R 1 Each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl having 1-20 carbon atoms, cycloalkyl having 3-20 ring carbon atoms, heteroalkane having 1-20 carbon atoms Base, aralkyl group having 7-30 carbon atoms, alkoxy group having 1-20 carbon atoms, aryloxy group having 6-30 carbon atoms, aryl group having 6-30 carbon atoms...

Embodiment 1

[0069] according to Figure 5 The reaction equation shown prepares 1,2-diphenyl-3H-pyrrolo[1,2-a]indol-3-one (formula I-a)

[0070] into a 25mL Schlenk bottle under N 2 Under the protection of N,N-diphenyl-1H-indole-1-carboxamide (0.5mmol, 156.2mg), 1,2-diphenylacetylene (1.25mmol, 222.8mg), Re 2 (CO) 10 (0.025mmol, 16.3mg), a mixture of zinc chloride (0.15mmol, 20.4mg), dimethylzinc (0.15mmol, 1.2M, 0.125mL) and anhydrous toluene (2.5mL) was heated to 150°C for 24h, After the reaction was completed, the reaction solution was diluted with DCM and filtered through a thin layer of silica gel, which was washed with EA. After the filtrate was concentrated, it was separated by column chromatography (eluent: petroleum ether: dichloromethane = 5 / 1, v / v) to obtain 141.2 mg of the target product (Formula I-a), with a yield of 88%.

[0071] The target product is characterized as follows: 1 H NMR (400MHz, CDCl 3 ): δ7.76(d,J=8.0Hz,1H),7.46-7.42(m,4H),7.40-7.35(m,4H),7.33–7.26(m,4H)...

Embodiment 2

[0073] according to Figure 6 The reaction equation shown prepares 7-methyl-1,2-diphenyl-3H-pyrrolo[1,2-a]indol-3-one (formula I-b)

[0074] into a 25mL Schlenk bottle under N 2 Under the protection of 5-methyl-N,N-diphenyl-1H-indole-1-carboxamide (0.5mmol, 163.2mg), 1,2-diphenylacetylene (1.25mmol, 222.8mg) , Re 2 (CO) 10 (0.025mmol, 16.3mg), a mixture of zinc chloride (0.15mmol, 20.4mg), dimethylzinc (0.15mmol, 1.2M, 0.125mL) and anhydrous toluene (2.5mL) was heated to 150°C for 24h, After the reaction was completed, the reaction solution was diluted with DCM and filtered through a thin layer of silica gel, which was washed with EA. After the filtrate was concentrated, it was separated by column chromatography (eluent: petroleum ether: dichloromethane = 5 / 1, v / v) to obtain 164.2 mg of the target product (Formula I-a), with a yield of 98%.

[0075] The target product is characterized as follows: 1 H NMR (500MHz, CDCl 3 ):δ7.64(d,J=8.1Hz,1H),7.47–7.41(m,4H),7.41–7.34(m,...

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Abstract

The invention relates to the technical field of organic chemical synthesis, in particular to a method for preparing an indolo-pyrrolidone compound. The method comprises the following steps that in thepresence of a catalyst, Lewis acid and a zinc reagent, an indole compound shown in formula II and alkyne shown in formula III are subjected to a C-H bond activation / C-N bond cleavage reaction, and the indolo-pyrrolidone compound shown in formula I is obtained. According to the method, indole and alkyne react with each other in a solvent in the presence of the catalyst, the Lewis acid and the zincreagent, and therefore the synthesis of the indolo-pyrrolidone compound is achieved.

Description

technical field [0001] The invention relates to the field of organic chemical synthesis, in particular to a method for preparing indolopyrrolone compounds. Background technique [0002] Indolopyrrolone compound is an important nitrogen-containing heterocyclic compound, which widely exists in nature. It has a variety of biological activities and special chemical properties, and can be used as the active structural unit of many natural products and drugs, and has important research value and application prospects in the fields of organic synthesis, medicine and chemical industry. [0003] The preparation methods of indolopyrrolone compounds in the prior art mainly include: the following methods are disclosed in J.Org.Chem.2017,82,5263-5273: (such as figure 1 shown); it uses a ruthenium catalyst to catalyze the reaction of indole and alkyne to produce indolopyrrole compound, but the R' substituent in the substrate alkyne used is mainly methyl, although there are also examples ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04
Inventor 王从洋杨芸辉
Owner INST OF CHEM CHINESE ACAD OF SCI