2-cyano-substituted indole compound and synthetic method thereof

A technology of indole compound and cyano group substitution, applied in the direction of organic chemistry, etc., can solve the problems of complex and harsh reaction conditions, difficulty in introducing functional groups, unsatisfactory yield, etc., and achieve the effects of moderate conditions, simple operation, and environmental protection of the reaction.

Inactive Publication Date: 2012-10-03
SHANGHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For indole, because the activity of the 3-position H is higher than that of the 2-position H, it is difficult to introduce a functional group at the 2-position of indole during the reaction, and the known cyanation reaction conditions of the 2-position of indole are complex and harsh. , the yield is not ideal

Method used

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  • 2-cyano-substituted indole compound and synthetic method thereof
  • 2-cyano-substituted indole compound and synthetic method thereof
  • 2-cyano-substituted indole compound and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1: 1-(pyrimidine-2)-1 H - Preparation of indole-2-cyano

[0030] 1-(pyrimidine-2)-1 H -Indole-2-cyano group adopts the following steps: 1. add 9.8 grams of 1-(pyrimidine-2)-1 in a 250 ml round bottom flask H - Indole, 560 mg of palladium acetate, 43 g of additives, 12.5 g of tert-butylisonitrile, 150 ml of N,N-dimethylformamide, heated to 130°C. Track the reaction with thin layer chromatography until the reaction raw material 1-(pyrimidine-2)-1 H -Indole disappears; 2. After the reaction is finished, add 3 N ammonia solution to the system, extract the product with ethyl acetate, remove the solvent with a rotary evaporator after drying, and obtain the crude product; 3. Column chromatography (petroleum ether) for the crude product : ethyl acetate = 6 : 1) purification to obtain 10.1 g of 1-(pyrimidine-2)-1 H -Indole-2-cyano, yield 92%. Melting point: 120-121°C.

[0031] -1 2225, 1572, 1531, 1449, 1427, 1256, 812, 739, 625.

[0032] 1 H NMR (CDCl 3...

Embodiment 2

[0036] Example 2: 5-methoxy-1-(pyrimidine-2)-1 H - Preparation of indole-2-cyano

[0037] 5-methoxy-1-(pyrimidine-2)-1 H -Indole-2-cyano group adopts the following steps: ①Add 11.2 grams of 5-methoxyl-1-(pyrimidine-2)-1 in a 250 ml round bottom flask H - Indole, 560 mg of palladium acetate, 43 g of additives, 12.5 g of tert-butylisonitrile, 150 ml of N,N-dimethylformamide, heated to 130°C. Track the reaction with thin-layer chromatography until the reaction raw material 5-methoxy-1-(pyrimidine-2)-1 H -Indole disappears; 2. After the reaction is finished, add 3 N ammonia solution to the system, extract the product with ethyl acetate, remove the solvent with a rotary evaporator after drying, and obtain the crude product; 3. Column chromatography (petroleum ether) for the crude product : Ethyl acetate=6 : 1) purification to obtain 10.2 grams of 5-methoxyl-1-(pyrimidine-2)-1 H -Indole-2-cyano, yield 85%. Melting point: 176-178°C.

[0038] -1 2219, 1570, 1529, 1453, 1440,...

Embodiment 3

[0043] Example 3: Methyl 6-formate-(pyrimidine-2)-1 H - Preparation of indole-2-cyano

[0044] 6-Methyl carboxylate-(pyrimidine-2)-1 H -Indole-2-cyano group adopts the following steps: 1. add 12.6 grams of 6-methyl formate-(pyrimidine-2)-1 in a 250 ml round bottom flask H - Indole, 560 mg of palladium acetate, 43 g of additives, 12.5 g of tert-butylisonitrile, 150 ml of N,N-dimethylformamide, heated to 130°C. Track the reaction with thin-layer chromatography until the reaction raw material 6-formic acid methyl ester-(pyrimidine-2)-1 H -indole disappears; 2. after the reaction is finished, add 3 N ammonia solution to the system, extract the product with ethyl acetate, remove the solvent with a rotary evaporator after drying, and obtain the crude product; 3. use column chromatography (petroleum ether) for the crude product : Ethyl acetate=6 : 1) Purification to obtain 4.9 g of 6-methyl carboxylate-(pyrimidine-2)-1 H -Indole-2-cyano, yield 35%. Melting point: 178-180°C.

[...

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Abstract

The invention relates to a 2-cyano-substituted indole compound and a synthetic method thereof. The structural formula of the compound is shown in the specifications, wherein R1 is pyridyl or pyrimidinyl; and R is methyl, methoxyl, bromine or -CO2Me. The 2-cyano-substituted indole compound prepared with the method is a type of important organic synthetic intermediate. The method has the advantages of readily-available raw materials, high reaction selectivity, adoption of novel isocyanide as a cyano source, use of the conventional solvent in a reaction, easiness for operating, appropriate reactions, environment-friendly reaction, maximum reaction yield of up to 92 percent, applicability to industrial production and the like.

Description

technical field [0001] The invention relates to a cyano-substituted indole compound and a synthesis method thereof, mainly a 2-cyano-substituted indole compound and a preparation method thereof. Background technique [0002] Organic cyanides are a very important class of compounds in organic synthesis. Cyano compounds are not only important pharmaceutical intermediates, but also important structures of pigments, dyes, etc., and they are easily converted into other useful functional group compounds, such as aldehydes, ketones, carboxylic acids, amines, and amides. In organic synthesis, the formation of carbon-cyanide bonds is one of the most basic ways to synthesize organic cyanides. Indole widely exists in natural compounds and is a very important heterocyclic compound. It is a very effective and novel method to realize the introduction of cyano group in the indole skeleton through the method of carbon-hydrogen bond activation. [0003] The synthetic cyano compound method...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/42
Inventor 许斌徐曙光常广军刘文婷刘秉新
Owner SHANGHAI UNIV
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