Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Method for synthesizing bisindole derivative

A technology of bis-indole derivatives and indole derivatives, applied in organic chemistry and other fields, can solve the problems of harsh reaction conditions and high toxicity of aldehyde compounds, and achieve the effect of simple steps, low toxicity and high yield

Inactive Publication Date: 2018-06-29
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
View PDF0 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Through the reaction of indole derivatives and aldehyde compounds under the catalysis of Lewis acid or transition metal, although bis-indole compound derivatives can be effectively prepared (Tetrahedron 2011, 67, 3420.), but the toxicity of aldehyde compounds exists, the reaction Harsh conditions and other disadvantages limit the application of these methods

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Method for synthesizing bisindole derivative
  • Method for synthesizing bisindole derivative
  • Method for synthesizing bisindole derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031]

[0032] In a 10mL reaction flask, add N-methylindole (2a) (66mg, 0.5mmol), 3-dimethylaminoacrylonitrile (3) (48mg, 0.5mmol), dichloroacetic acid (645mg, 5.0mmol) in sequence ) and 2mL solvent dichloroethane, stirred at 50°C for 4h. After the reaction is completed, the reaction solution is poured into a separatory funnel, and 10 mL of saturated aqueous sodium bicarbonate solution is added thereto, shaken, left to stand, and the oil-water phase is separated, and the water phase is extracted with dichloromethane (2 × 5 mL), and the organic Mutually. The organic phases were mixed, dried over anhydrous sodium sulfate, and filtered. The volatile components were removed under reduced pressure, and then separated by silica gel column chromatography (dichloromethane as the eluent) to obtain the target product (1a) (128 mg, yield 82%) as a white solid. The target product was confirmed by NMR and high-resolution mass spectrometry. (Reaction 2)

Embodiment 2

[0034] The reaction steps and operations are the same as in Example 1, except that the reaction time is 12 hours. The reaction was stopped, and the target product 1a (127 mg, yield 81%) was obtained after post-treatment.

Embodiment 3

[0036] The reaction steps and operations are the same as in Example 1, except that the reaction time is 1 h. The reaction was stopped, and the target product 1a (47 mg, yield 30%) was obtained after post-treatment.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a method for synthesizing a bisindole derivative. An indole derivative which is cheap and easy to obtain and rich in structure diversity is adopted as a raw material which is reacted with 3-dimethylamino acrylonitrile in the presence of an acid, and the bisindole derivative can be synthesized. Compared with a reported bisindole derivative synthesis method, the method has the advantages of being cheap and easy in raw material obtaining, low in toxicity, simple and convenient to operate, gentle in synthesis reaction condition, high in efficiency, and the like.

Description

technical field [0001] The invention relates to a method for synthesizing bis-indole derivatives by reacting cheap, easy-to-obtain and structurally diverse indole derivatives with 3-dimethylaminoacrylonitrile in the presence of acid. Compared with the reported synthesis method of bisindole derivatives, the present invention has cheap and easy-to-obtain raw materials, low toxicity, simple operation, mild synthesis reaction conditions and high efficiency. Background technique [0002] Bisindole compounds and their derivatives are important pharmaceutical intermediates and are widely used in the fields of medicine, pesticide and chemical industry. Through the reaction of indole derivatives and aldehyde compounds under the catalysis of Lewis acid or transition metal, although bis-indole compound derivatives can be effectively prepared (Tetrahedron 2011, 67, 3420.), but there are aldehyde compounds that are highly toxic and the reaction Harsh conditions and other disadvantages l...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/06
CPCC07D403/06
Inventor 吴凯凯余正坤
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com