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

Method for synthesizing fluorine-containing quinolinone compound by electro-catalyzing indole by using electrochemical micro-channel reaction device

A technology of microchannel reaction and quinolinones, which is applied in the direction of electrolytic components, electrolytic process, electrolytic organic production, etc., can solve the problems of high price and limited development, and achieve easy storage, shorten reaction time, and reduce the generation of by-products Effect

Active Publication Date: 2021-02-26
NANJING UNIV OF TECH
View PDF2 Cites 3 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the high price of Ir or Ru-based photoredox catalysts also limits its development.

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 fluorine-containing quinolinone compound by electro-catalyzing indole by using electrochemical micro-channel reaction device
  • Method for synthesizing fluorine-containing quinolinone compound by electro-catalyzing indole by using electrochemical micro-channel reaction device
  • Method for synthesizing fluorine-containing quinolinone compound by electro-catalyzing indole by using electrochemical micro-channel reaction device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0065]

[0066] Microchannel reaction device see figure 2 , the reactants are as shown above, take R 1 is p methyl, R 2 is methyl, R 3 for hydrogen, R 4 N-substituted 2-arylindole reactant 0.058g (0.2mmol, 1.0equiv) that is methyl is dissolved in 3mL mixed solvent (H 2 O:MeOH=1:5) to obtain the first solution, weigh the trifluoromethyl source CF 3 SO 2 Na 0.062g (0.4mmol, 2.0equiv), electrolyte Et 4 NClO 4 0.092g (0.4mmol, 2.0equiv), with 3mL mixed solvent (H 2 (0:MeCN=1:5) was dissolved to obtain the second solution, which was loaded into syringes after being completely dissolved. The first solution and the second solution are simultaneously pumped into a reactor with a coil inner diameter of 0.5mm and mixed, the volume is 6mL, the flow rates of the first solution and the second solution are both 0.2mL / min, and pumped into the electrochemical microreactor , the anode is a carbon electrode, and the cathode is a platinum electrode. The reaction is carried out at a...

Embodiment 2

[0068] The method is the same as in Example 1, except that the electrolyte is changed to Et 4 NPF 6 0.11g (0.4mmol, 2.0equiv), TLC detection was performed after the reaction, and 70.82mg of the final product was obtained by EA:PE=1:10 silica gel column chromatography, with a yield of 91%.

Embodiment 3

[0070] The method is the same as in Example 1, except that the electrolyte is changed to nBu 4 NClO 4 0.11g (0.4mmol, 2.0equiv), TLC detection was performed after the reaction, and 69.5mg of the final product was obtained by EA:PE=1:10 silica gel column chromatography, with a yield of 89.3%.

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 fluorine-containing quinolinone compound by electro-catalyzing indole by using an electrochemical micro-channel reaction device, which is characterized by comprising the following steps of respectively and simultaneously pumping a first solution containing an N-substituted 2-aryl indole compound shown as a formula I with a second solution containing a fluorine source and an electrolyte, reacting to obtain a reaction solution containing the fluorine-containing quinolinone compound as shown in the formula II. The micro-channel reaction device is used for preparing the fluorine-containing quinolinone compound, the reaction rate can be effectively controlled, the reaction time is shortened, continuous production is achieved, high diastereoselectivity is achieved, generation of by-products is reduced, the maximum yield can reach 98.7%, the refining process is simpler, and the product quality is improved; basically no amplification effect exists, and industrial amplification is facilitated.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and specifically relates to a method for synthesizing fluorine-containing quinolinone compounds by using an electrochemical microchannel reaction device to electrocatalyze indole fluorination, cyclization and cracking. Background technique [0002] Organofluorine compounds are of great interest in organic synthesis, pharmaceuticals, and agrochemical applications due to their synthetic utility and unique biological activities. Therefore, methods for incorporating fluoroalkyl groups into pharmaceutical or bioactive molecules continue to be in strong demand, since the addition of such groups can significantly alter their metabolic stability, lipophilicity, and bioactivity. Among existing methods, free radical-initiated fluoroalkylation / cyclization of unactivated alkenes is one of the most promising strategies for the synthesis of complex fluorochemicals, which requires the selection of su...

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
IPC IPC(8): C25B3/11C25B3/09C25B3/05C25B3/07C25B3/28C25B9/17C25B15/08
CPCC25B15/08
Inventor 郭凯孙蕲袁鑫邱江凯覃龙洲段秀庄恺强崔玉声陈琳
Owner NANJING 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