Synthesis method of copper-promoted 3-cyano-substituted-indole compound

A technology of indole compound and cyano group substitution, applied in organic chemistry and other directions, can solve the problems of easy poisoning, high price and high substrate requirements of Pd catalysts

Inactive Publication Date: 2015-07-22
HUNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This type of method uses a variety of metal catalysts, among which Pd catalysts are prone to poisoning, expensive, have high requirements for substrates, and have complicated reaction steps

Method used

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  • Synthesis method of copper-promoted 3-cyano-substituted-indole compound
  • Synthesis method of copper-promoted 3-cyano-substituted-indole compound

Examples

Experimental program
Comparison scheme
Effect test

Synthetic example 1

[0023] Synthesis of 3-cyanindole

[0024] Add 0.2 mmol of indole, 0.3 mmol of cuprous chloride, 0.4 mmol of tetramethylethylenediamine, and then add 1 ml of a mixed solvent (the volume ratio of acetonitrile and DMAc is [7:3]) into the reaction vessel. Under an oxygen atmosphere, heat to 120°C, continue to stir for 24 hours, stop the reaction, cool to room temperature, extract with ethyl acetate, dry, and distill off the solvent under reduced pressure. The crude product is separated by column chromatography to obtain the target product with a yield of 41%. . 1 H NMR (400MHz, DMSO) δ12.24(s, 1H), 8.29(s, 1H), 7.67(d, J=7.6Hz, 1H), 7.59(d, J=8.0Hz, 1H), 7.31(t ,J=7.4Hz,1H),7.26(t,J=7.4Hz,1H).

Synthetic example 2

[0026] Synthesis of N-methylindole-3-cyano

[0027] Add 0.2mmol N-methylindole, 0.3mmol of cuprous chloride, 0.4mmol of tetramethylethylenediamine in the reaction vessel, then add 1ml of mixed solvent (the volume ratio of acetonitrile and DMAc is [7:3] ). Under an oxygen atmosphere, heat to 130°C, continue to stir for 24 hours, stop the reaction, cool to room temperature, extract with ethyl acetate, dry, and distill off the solvent under reduced pressure. The crude product is separated by column chromatography to obtain the target product with a yield of 93%. . 1 H NMR (400MHz, CDCl 3 )δ7.76(d, J=7.9Hz, 1H), 7.56(s, 1H), 7.40(d, J=8.0Hz, 1H), 7.36(t, J=7.4Hz, 1H), 7.30(t, J=7.3Hz,1H),3.85(s,3H).

Synthetic example 3

[0029] Synthesis of 1,2-Dimethylindole-3-cyano

[0030] In reaction vessel, add 0.2mmol 1,2-dimethylindole, the cuprous chloride of 0.32mmol, the tetramethylethylenediamine of 0.45mmol, then add 1ml mixed solvent (the volume ratio of acetonitrile and DMAc is [7 :3]). Under an oxygen atmosphere, heat to 130°C, continue to stir for 24 hours, stop the reaction, cool to room temperature, extract with ethyl acetate, dry, and distill off the solvent under reduced pressure. The crude product is separated by column chromatography to obtain the target product with a yield of 85%. . 1 H NMR (400MHz, CDCl 3 )δ7.67(d,J=7.2Hz,1H),7.32-7.24(m,3H),3.72(s,3H),2.59(s,3H).

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Abstract

The invention provides a synthesis method of a copper-promoted 3-cyano-substituted-indole compound. According to the method, a copper reagent which is cheap and easy to obtain is used as a medium, an indole compound, TMEDA (tetramethylethylenediamine) and acetonitrile are used as raw materials, and the 3-cyano-substituted-indole compound is synthesized. The method has the advantages as follows: the raw materials are cheap and easy to obtain, the TMEDA and the acetonitrile are used as sources of cyano-groups, usage of higher-toxicity cyanide is avoided, special reaction conditions such as ligands, acids, bases, superoxides, microwave radiation and the like are not adopted, operation is simple, conditions are moderate, the yield is higher, and the method has the broad industrial application prospect.

Description

【Technical field】 [0001] The invention relates to the field of organic synthesis, in particular to a method for synthesizing copper-promoted 3-cyano-substituted indole compounds. 【Background technique】 [0002] 3-cyano-substituted indole compounds are very important organic intermediates in organic synthesis. The cyano groups contained in 3-cyano-substituted indole compounds can be effectively converted into other useful functional groups, such as aldehydes, ketones, carboxylic acids, amines, and amides. Therefore, it is widely used in the synthesis of aldehydes, ketones and carboxylic acid derivatives, amines and amides in the field of organic synthesis. At the same time, it has also been widely used in the fields of pharmaceutical synthesis, organic pesticide and dye synthesis. Therefore, the simple and efficient synthesis of 3-cyano-substituted indole compounds has important scientific significance and potential application prospects. [0003] At present, many syntheti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/42C07D471/04
CPCC07D209/42C07D471/04
Inventor 周永波李中文董建玉尹双凤韩立彪
Owner HUNAN UNIV
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