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
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Problems solved by technology

However, the high price of Ir or Ru-based pho

Method used

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  • 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

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Experimental program
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Example Embodiment

[0064]Example 1

[0065]

[0066]Microchannel reaction device seefigure 2 , The reactant is shown above, take R1Is p methyl, R2Is methyl, R3Is hydrogen, R40.058g (0.2mmol, 1.0equiv) of N-substituted 2-aryl indole reactant of methyl is dissolved in 3mL mixed solvent (H2O:MeOH=1:5) to obtain the first solution, weigh the trifluoromethyl source CF3SO2Na 0.062g (0.4mmol, 2.0equiv), electrolyte Et4NClO4 0.092g (0.4mmol, 2.0equiv), using 3mL mixed solvent (H2O: MeCN=1:5) dissolve to obtain the second solution, and load the second solution into the syringe after it is completely dissolved. The first solution and the second solution were simultaneously pumped into a reactor with a coil inner diameter of 0.5mm, and the volume was 6mL. The flow rates of the first solution and the second solution were both 0.2mL / min, and pumped into the electrochemical microreactor , The anode is a carbon electrode, the cathode is a platinum electrode, the reaction is carried out at a constant current of 5mA, 25°C, ...

Example Embodiment

[0067]Example 2

[0068]The method is the same as in Example 1, except that the electrolyte is changed to Et4NPF6 0.11 g (0.4 mmol, 2.0 equiv), TLC detection was performed after the reaction, and 70.82 mg of the final product was obtained by silica gel column chromatography with EA:PE=1:10, and the yield was 91%.

Example Embodiment

[0069]Example 3

[0070]The method is the same as in Example 1, except that the electrolyte is changed to nBu4NClO4 0.11 g (0.4 mmol, 2.0 equiv), TLC detection was performed after the reaction, and 69.5 mg of the final product was obtained by silica gel column chromatography with EA:PE=1:10, with a yield of 89.3%.

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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

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Application Information

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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
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