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

Electrochemical synthetic method of 3-bromine-2-phenyl-imidazo-[1,2-alpha] pyridine derivative

A technology of pyridine derivatives and synthesis method, which is applied in the field of synthesis of 3-bromo-2-phenyl-imidazo[1,2-α]pyridine derivatives, achieves wide application range, avoids multi-step operation, mild conditions

Inactive Publication Date: 2017-06-30
SOUTH CHINA UNIV OF TECH
View PDF5 Cites 7 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Notably, the one-step synthesis of halogen-substituted imidazo[1,2-α]pyridines has rarely been reported

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
  • Electrochemical synthetic method of 3-bromine-2-phenyl-imidazo-[1,2-alpha] pyridine derivative
  • Electrochemical synthetic method of 3-bromine-2-phenyl-imidazo-[1,2-alpha] pyridine derivative
  • Electrochemical synthetic method of 3-bromine-2-phenyl-imidazo-[1,2-alpha] pyridine derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] Add 99.5mg (0.5mmol) 2-bromoacetophenone, 70.5mg (0.75mmol) 2-aminopyridine, 36.9mg (the concentration in the electrolyte is 0.02mol / L, the same below) to a 5ml round bottom bottle TBAI; 117.5mg (the concentration in the electrolyte is 0.2mol / L, the same below) NH 4 ClO 4 ; Then add dimethyl sulfoxide 5ml. Insert two electrodes (the platinum wire is the anode, and the platinum sheet is the cathode), the DC power supply is 5mA, the reaction is stirred, and the reaction is monitored by TLC, and the reaction is complete in 10 hours. The crude product was extracted with ethyl acetate (15ml×3), the organic layers were combined, washed with saturated NaCl aqueous solution (10ml×1), anhydrous NaCl 2 SO 4 After drying and evaporating to dryness under reduced pressure, the product 3a was isolated with a yield of 91%.

[0060] Add 99.5mg (0.5mmol) 2-bromoacetophenone, 70.5mg (0.75mmol) 2-aminopyridine, 36.9mg (0.02mol / L) TBAI; 117.5mg (0.2mol / L) to a 5ml round bottom bottle ...

Embodiment 2

[0064] Add 99.5mg (0.5mmol) 2-bromoacetophenone, 81.0mg (0.75mmol) 5-methyl-2-aminopyridine, 36.9mg (0.02mol / L) TBAI, 117.5mg ( 0.2mol / L)NH 4 ClO 4 ; Then add dimethyl sulfoxide 5ml. Insert two electrodes (the platinum wire is the anode, and the platinum sheet is the cathode), the DC power supply is 5mA, the reaction is stirred, and the reaction is monitored by TLC, and the reaction is complete in 10 hours. The crude product was extracted with ethyl acetate (15ml×3), the organic layers were combined, washed with saturated NaCl aqueous solution (10ml×1), anhydrous NaCl 2 SO 4 After drying and evaporating to dryness under reduced pressure, the product 3b was isolated with a yield of 86%.

[0065]

Embodiment 3

[0067] Add 99.5mg (0.5mmol) 2-bromoacetophenone, 96.0mg (0.75mmol) 5-chloro-2-aminopyridine, 36.9mg (0.02mol / L) TBAI, 117.5mg (0.2 mol / L) NH 4 ClO 4 ; Then add dimethyl sulfoxide 5ml. Insert two electrodes (the platinum wire is the anode, and the platinum sheet is the cathode), the DC power supply is 5mA, the reaction is stirred, and the reaction is monitored by TLC, and the reaction is complete in 10 hours. The crude product was extracted with ethyl acetate (15ml×3), the organic layers were combined, washed with saturated NaCl aqueous solution (10ml×1), anhydrous NaCl 2 SO 4 After drying and evaporating to dryness under reduced pressure, the product 3c was isolated with a yield of 73%.

[0068]

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 an electrochemical synthetic method of a 3-bromine-2-phenyl-imidazo-[1,2-alpha] pyridine derivative. According to the method, a 2-bromoacetophenone compound and a 2-aminopyridine compound are added into DMSO containing an ammonium perchlorate electrolyte, a platinum sheet is served as the cathode, a platinum wire is served as an anode, stirring is performed at the room temperature, a constant-current reaction is performed, after the reaction is ended, reaction fluid is subjected to extraction, concentration and separation, and the 3-bromine-2-phenyl-imidazo-[1,2-alpha] pyridine derivative is obtained. Electricity is utilized to promote the reaction, an expensive metal catalyst is not needed, other oxidizing agents are not needed, heating is also not needed, the reaction can be performed at a mild room temperature, selectivity is good, and the whole process is simple and easy to perform and is consistent with the concept of green chemistry. An extra bromine source is not needed, extra oxidizing agents are also not needed, the electrochemical synthetic method is simple, efficient and wide in substrate application, and compounds with different substituent effect base groups can all achieve high yields.

Description

technical field [0001] The invention relates to the field of synthesis of 3-bromo-2-phenyl-imidazo[1,2-α]pyridine derivatives, in particular to 3-bromo-2-phenyl-imidazo[1,2-α]pyridine Electrochemical synthesis method of derivatives. Background technique [0002] The polysubstituted imidazo[1,2-α]pyridine skeleton has a special structure, which is ubiquitous in pharmacologically important compounds, natural products and drug molecules. They contain π-electron-deficient pyridine rings and π-electron-rich imidazole rings. Therefore, appropriately functionalized imidazo[1,2-α]pyridines are also excellent building blocks for synthetic frameworks in materials science as well as irregular N-heterocyclic carbenes in organometallic chemistry. Common imidazo[1,2-α]pyridine-derived drugs include saripidem, alpitant, and necopidem for the treatment of anxiolytics, zolpidem, and zolpidem, which is used for the treatment of antiulcer and insomnia, Opridone is used to strengthen the hea...

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): C25B3/02C25B3/23
CPCC25B3/23
Inventor 黄精美王海彬赖胤龙
Owner SOUTH CHINA UNIV OF TECH
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