3-cyan substituted indole compound and synthetic method thereof

A technology of indole compound and cyano group substitution, which is applied in the direction of organic chemistry, can solve the problems of high substrate requirements, complicated reaction steps, and difficulty in obtaining 3-position cyanolated products, so as to avoid metal cyanides and conditions Moderate, easy-to-operate effect

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

AI Technical Summary

Problems solved by technology

[0019] In summary, there are many methods for preparing 3-cyanindole, but these reactions have many defects, such as high requirements for substrates, complex reaction steps or the need to introduce a protecting group at the 2-position, and it is difficult to A single 3-position cyanation product is obtained, often a mixture

Method used

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  • 3-cyan substituted indole compound and synthetic method thereof
  • 3-cyan substituted indole compound and synthetic method thereof
  • 3-cyan substituted indole compound and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Example 1: 1-phenyl-1 H - Preparation of indole-3-cyano

[0045] 1-phenyl-1 H -Indole-3-cyano group adopts the following steps: 1. Add 9.7 grams of 1-phenyl-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, to the reaction raw material 1-phenyl-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 8.1 g of 1-phenyl-1 H -Indole-3-cyano, yield 74%. Melting point: 120-121°C.

[0046] IR (KBr, cm -1 ): 2223, 1599, 1539, 1501, 1458, 1224, 736, 694.

[0047] 1 H NMR (CDCl 3 , 500 MHz): δ = 7.85-7....

Embodiment 2

[0050] Example 2: 1-(4-fluoro-phenyl)-1 H - Preparation of indole-3-cyano

[0051] 1-(4-fluoro-phenyl)-1 H -Indole-3-cyano uses the following steps: ①Add 10.5 grams of 1-(4-fluoro-phenyl)-1 to 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-(4-fluoro-phenyl)-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 7.4 g of 1-(4-fluoro-phenyl)-1 H -Indole-3-cyano, yield 63%. Melting point: 164-167°C.

[0052] IR (KBr, cm -1 ): 2227, 1539, 1515, 1460, 1215, 837, 740.

[0053] 1 H N...

Embodiment 3

[0058] Example three: 1-(4-methoxy-phenyl)-1 H - Preparation of indole-3-cyano

[0059] 1-(4-Methoxy-phenyl)-1 H -Indole-3-cyano uses the following steps: ①Add 11.1 grams of 1-(4-methoxy-phenyl)-1 to a 250-ml round-bottomed 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-(4-methoxy-phenyl)-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 4.6 grams of 1-(4-methoxy-phenyl)-1 H -Indole-3-cyano, yield 36%. Melting point: 126-129°C.

[0060] IR (KBr,cm –1 ): 2219, 1535, 1513, 1458, 1245, 1219, 1028, 836,...

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Abstract

The invention relates to a 3-cyan substituted indole compound and a synthetic method thereof. The constitutional formula of the compound is that R1 is a methoxy group, and R2 is phenyl (Ph), benzyl (Bn), allyl or n-butyl. According to the synthetic method of the 3-cyan substituted indole compound, raw materials are easy to obtain, novel tertiary butyl isonitrile is firstly used as a source of cyan, and high toxic metal cyanide is avoided to be used. During the reaction, conventional reaction solvents are used, the operation is simple, the operation condition is moderate, the reaction is environment-friendly, the top yield can reach 74%, and the 3-cyan substituted indole compound has a good application prospect in industrial production.

Description

technical field [0001] The invention relates to a cyano-substituted indole compound and a preparation method thereof, mainly a 3-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 drug intermediates, but also important structures of pigment dyes, and they are easily converted into other useful functional group compounds, such as aldehydes, ketones, carboxylic acids, amines and amides, etc., through carbon-carbon bonds The introduction of cyano groups into organic compound molecules is one of the most basic ways in organic synthesis. Indole widely exists in natural compounds and is a very important heterocyclic compound. For example, escitalopram containing cyano group, Lexapro is a very effective antidepressant drug; Fulong femara containing two cyano groups is an effective drug for adjuvant treatment of early ...

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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