Method for continuous electrosynthesis of isoindolinone by using micro-reaction device

An isoindolinone, electrosynthesis technology, applied in chemical instruments and methods, chemical/physical/physical-chemical reactors, electrolysis processes, etc., can solve problems such as the need for oxidants and harsh reaction conditions, and achieve easy operation and reaction. Mild conditions, the effect of avoiding decomposition

Active Publication Date: 2021-10-26
NANJING ADVANCED BIOLOGICAL MATERIALS & PROCESS EQUIP INST CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Purpose of the invention: the technical problem to be solved in the present invention is to develop a novel electrosynthesis method for isoindolinone, which overcomes the harsh reaction conditions of the traditional system and requires oxidants and metals

Method used

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  • Method for continuous electrosynthesis of isoindolinone by using micro-reaction device
  • Method for continuous electrosynthesis of isoindolinone by using micro-reaction device
  • Method for continuous electrosynthesis of isoindolinone by using micro-reaction device

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Experimental program
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Embodiment 1

[0031] The synthesis of embodiment 1 compound III:

[0032] Dissolve 0.5mmol (0.0886g) of compound I, 1.5mmol (0.234g) of sodium trifluoromethanesulfinate II and 1mmol (0.302g) of tetrabutylammonium acetate in acetonitrile / water (10mL, volume ratio 4 / 1 , the same below), to obtain a homogeneous solution A, which was added to the syringe pump a; the injection flow rate of the syringe pump a was 225 μL / min; the applied current was 10 mA; the microchannel reactor reaction volume V=225 μL, and the reaction time was 1 min; After one period of reaction in the microchannel reactor, the reaction liquid was collected, and the product yield calculated by HPLC was 84%, and the product III was obtained after separation by column chromatography. 1 H NMR (400MHz, Chloroform-d) δ7.74 (d, J = 7.5Hz, 1H), 7.53 (d, J = 7.6Hz, 1H), 7.44–7.37 (m, 2H), 4.86 (dd, J = 6.7,4.0Hz,1H),3.88(s,3H),2.97–2.78(m,1H),2.55–2.40(m,1H). 13 C NMR (101MHz, Chloroform-d) δ164.7, 140.7, 132.6, 129.3, 129.2, 125.2...

Embodiment 2

[0033] The synthesis of embodiment 2 compound III:

[0034] Dissolve 0.5mmol (0.0886g) of compound I, 1.5mmol (0.234g) of sodium trifluoromethanesulfinate II and 1mmol (0.387g) of tetrabutylammonium hexafluorophosphate in acetonitrile / water (10mL, with a volume ratio of 4 / 1, the same below), to obtain a homogeneous solution A, add in the syringe pump a; the injection flow rate of the syringe pump a is 225 μL / min; the applied current is 10mA; the microchannel reactor reaction volume V=225 μL, and the reaction time is 1min ; After a period of reaction in the microchannel reactor, the reaction liquid was collected, and the product yield was calculated by HPLC to be 77%, and the product III was obtained after separation by column chromatography.

Embodiment 3

[0035] The synthesis of embodiment 3 compound III:

[0036] Dissolve 0.5mmol (0.0886g) of compound I, 1.5mmol (0.234g) of sodium trifluoromethanesulfinate II and 1mmol (0.329g) of tetrabutylammonium tetrafluoroborate in acetonitrile / water (10mL, with a volume ratio of 4 / 1, the same below), to obtain a homogeneous solution A, add in the syringe pump a; the injection flow rate of the syringe pump a is 225 μL / min; the applied current is 10mA; the microchannel reactor reaction volume V=225 μL, and the reaction time is 1min ; After a period of reaction in the microchannel reactor, the reaction liquid was collected, and the product yield was calculated by HPLC to be 74%, and the product III was obtained after separation by column chromatography.

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Abstract

The invention discloses a novel method for continuous electrochemical synthesis of isoindolinone, which comprises the following steps of by taking N-methoxy-2-vinyl benzamide I and sodium trifluoromethanesulfinate II as reaction raw materials, carrying out continuous electrolytic reaction in a micro-channel reaction device in the presence of an electrolyte and a solvent, and carrying out an intramolecular free radical cascade reaction to obtain trifluoromethyl functionalized isoindolinone III. The reaction process is shown as a reaction formula. Compared with the prior art, the novel isoindolinone preparation method provided by the invention is green, safe and efficient in process operation and mild in reaction condition.

Description

technical field [0001] The invention belongs to the field of organic electrosynthesis, and in particular relates to a method for continuously electrosynthesizing isoindolinone by using a micro-reaction device. Background technique [0002] Isoindolinones are a class of key structural motifs frequently found in many natural products, pharmacologically active compounds and materials. They have attracted intense interest due to their outstanding biological activities and diverse synthetic applications in the preparation of complex molecular frameworks. Cascade reactions mediated by free radicals provide one of the most efficient methods for the preparation of functionalized isoindolinone compounds. [0003] Currently, methods for constructing trifluoromethyl-functionalized isoindolinone compound skeletons include: (1) Copper-catalyzed intramolecular aminotrifluoromethylation of alkenes to prepare trifluoromethyl-functionalized isoindolinones , see references (Org.Chem.Front.,...

Claims

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Application Information

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IPC IPC(8): C25B3/09C25B3/23B01J19/00
CPCC25B3/09C25B3/23B01J19/0093
Inventor 季栋沈磊李玉光花加伟方正郭凯
Owner NANJING ADVANCED BIOLOGICAL MATERIALS & PROCESS EQUIP INST CO LTD
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