3-cyanoindole compound synthesis method

A technology of cyanoindole and synthesis method, applied in directions such as organic chemistry, can solve problems such as high price, easy poisoning of Pd catalyst, and achieve the effects of mild reaction conditions, simple operation method and low production cost

Active Publication Date: 2012-12-12
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Use multiple metal catalysts in this method, wherein Pd catalyst is easily poisoned, and the price is expensive, and the substrate is N-methylindole

Method used

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  • 3-cyanoindole compound synthesis method

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Experimental program
Comparison scheme
Effect test

Embodiment 1-20

[0019] Example R 1 R 2 R 3 1 H H H 2 H CH 3 H 3 H Ph H 4 H H 5-OCH 3 5 H H 5-Cl 6 H H 4-Cl 7 H H 5-F 8 H H 6-COOCH 3 9 H H 5-NO 2 10 H (4-F)-Ph H 11 H H 5-CN 12 H H 5-CH 3 13 CH 3 H H 14 CH 3 H 5-NO 2 15 CH 3 H 5-CN 16 CH 3 H 5-OCH 3 17 CH 3 H 5-CH 3 18 CH 3 Ph 5-OCH 3 19 CH 2 CH 3 CH 3 H 20 CH 2 CH 3 Ph H

Embodiment 1

[0021] Room temperature (20-35 o C) Add indole (1.0mmol), CuI (1.2mmol), phenylacetonitrile (1.2mmol) and DMF (5ml) in turn to the reaction flask, then stir and heat to 100 o C reaction until the PLC tracking indole reaction is complete. After the reaction, the reaction solution was cooled to room temperature, then added to 20ml of water, and extracted three times with dichloromethane, using 10ml of dichloromethane each time, separated by silica gel chromatography column, and distilled under reduced pressure. The yield was 80%, and the identification result was: 1 H NMR (400 MHz, CDCl 3 ) δ 8.80 (s, 1H), 7.78 (dd, J = 8.2, 7.2 Hz, 1H), 7.76 (s, 1H), 7.48 (dd, J = 8.3, 6.8 Hz, 1H), 7.39 – 7.28 (m, 2H). 13 C NMR (126 MHz, CDCl 3 ) δ 135.00, 132.05, 127.09, 124.45, 122.52, 119.80, 116.05, 112.23, 87.53.

Embodiment 2

[0023] Room temperature (20-35 o C) Add 2-methylindole (1.0mmol), CuI (1.2mmol), phenylacetonitrile (1.2mmol) and DMF (5ml) in turn in the reaction flask, then stir and heat to 100 o C reaction until the PLC tracking 2-methylindole reaction is complete. After the reaction, the reaction solution was cooled to room temperature, then added to 20ml of water, extracted three times with dichloromethane, each time using 10ml of dichloromethane, separated by silica gel chromatography, and distilled under reduced pressure. The yield was 37%, and the identification result was: 1H NMR (400 MHz, DMSO) δ 12.12 (s, 1H), 7.55 (d, J = 7.5 Hz, 1H), 7.47 (d, J = 7.8 Hz, 1H), 7.27 – 7.17 (m, 2H), 2.58 (s, 3H). 13 C NMR (101 MHz, DMSO) δ 146.90, 135.75, 128.13, 123.59, 122.31, 118.64, 117.42, 112.96, 83.75, 13.47.

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Abstract

The invention discloses a 3-cyanoindole compound synthesis method which includes: firstly, taking indole compound, benzyl cyanide and CuI according to the molar ratio of 1:1-2:1-2, placing the indole compound, the benzyl cyanide and the CuI in a reaction vessel, and adding solvent into the reaction vessel until the indole compound and the benzyl cyanide are completely dissolved; then, placing the reaction vessel in oil bath at the temperature of 100-130 DEG C with stirring for reaction for 30-34h, cooling to the room temperature, adding water as same as the solvent in volume, and extracting for 2-4 times by the aid of dichloromethane; and finally, separating by means of silica gel column chromatography prior to reduced pressure distillation so that the product, namely, the 3-cyanoindole compound is obtained. The 3-cyanoindole compound is synthesized by the aid of 'one-pot' reaction, and accordingly the intermediate separation and purification process is omitted, and the method is simple to operate, mild in reaction conditions, available in reaction raw materials, low in production cost and applicable to small-scale laboratorial preparation and large-scale industrial production.

Description

technical field [0001] The invention relates to a method for synthesizing organic compounds by cyanation, in particular to a method for synthesizing 3-cyanindole compounds. Background technique [0002] As important chemical intermediates, 3-cyanindole compounds are widely used in medicine, pesticide and other industries. At present, various methods for synthesizing 3-cyanindole compounds have been published. S. L. Buchwald (J. Am. Chem. Soc. 2003, vol 125, p2890-2891) et al reported the generation of 3-cyanindole from 3-bromoindole using CuI and KI with NaCN as the cyanide source Methods. In this method, NaCN is a highly toxic salt with great danger, and the substrate used is 3-bromoindole. Y. Kita (J. Org. Chem. 2007, vol 72, p109-116) et al reported starting from N-p-toluenesulfonyl indole, using PIFA and BF 3 ·Et 2 O, a method for generating 3-cyanindole using TMSCN as a cyanogen source. In this method, TMSCN is highly volatile, highly toxic and expensive, and the ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/42
Inventor 吕萍王彦广张莲鹏
Owner ZHEJIANG UNIV
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