Electrochemical synthesis method of 1,3-dimethyl-3-difluoroethyl-2-oxindole compound

A technology of indole compound and difluoroethyl, applied in the field of electrochemical synthesis of 1,3-dimethyl-3-difluoroethyl-2-oxindole compound, achieving high yield and mild reaction conditions , the effect of wide selection

Active Publication Date: 2021-02-02
HUNAN UNIV OF SCI & ENG
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  • Abstract
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  • Application Information

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Problems solved by technology

N-methyl-N-aryl acrylamide is a cheap and easy-to-obtain chemical raw material, which plays an important role in the fields of synthetic chemistry, but so far, there are no literature reports to use N-methyl-N-aryl Method for synthesizing 2-oxindole containing 1,1-difluoroethyl group using methacrylamide as initial raw material

Method used

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  • Electrochemical synthesis method of 1,3-dimethyl-3-difluoroethyl-2-oxindole compound
  • Electrochemical synthesis method of 1,3-dimethyl-3-difluoroethyl-2-oxindole compound
  • Electrochemical synthesis method of 1,3-dimethyl-3-difluoroethyl-2-oxindole compound

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Experimental program
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Effect test

Embodiment 1～5

[0046]The following Examples 1 to 5 are all reacted according to the following reaction equations, mainly to investigate the yields of different substrates under optimal conditions:

[0047]

[0048]The specific operation steps are as follows: in a 25mL three-necked round bottom flask, add N-methyl-N-arylacryloyl (0.5mmol), difluoroacetic acid (1mmol), potassium iodide (0.025mmol), HFIP (8mL), water in sequence (0.2mL), 15mm×15mm×3mm foamed copper electrode as anode, 15mm×15mm×3mm foamed zinc electrode as cathode. The resulting mixed solution was stirred and reacted for 12 hours under a DC current of 15 mA at room temperature. The thin-layer chromatography plate tracks the reaction process. After the reaction is completed, the extract is concentrated by a rotary evaporator, using petroleum ether / ethyl acetate as the eluent, and silica gel for column chromatography purification.

Embodiment 1

[0050]The yield is 95%,

[0051]5-chloro-3-(2,2-difluoroethyl)-1,3-dimethylindolin-2-one;

[0052]1H NMR(400MHz, CDCl3): δ7.23-7.19(m,1H), 7.14(d,J=2.0Hz,1H), 6.72(d, J=8.0Hz,1H), 5.57(tdd,J=56.0,6.4,3.6Hz, 1H), 3.13(s, 3H), 2.49-2.35(m, 1 H), 2.27-2.13(m, 1H), 1.33(s, 3H);

[0053]13C NMR(100MHz, CDCl3): δ178.7, 141.5, 133.8, 128.5, 128.2, 123.5, 114.9 (t, J = 238.5 Hz), 109.6, 44.8 (t, J = 5.2 Hz), 41.2 (t, J = 21.8 Hz), 26.5, 24.4.

Embodiment 2

[0055]Yield 88%

[0056]3-(2,2-difluoroethyl)-1,3,6-trimethylindolin-2-one;

[0057]1H NMR(400MHz, CDCl3): δ7.19(t,J=7.6Hz,1H), 6.89(d,J=8.0Hz,1H), 6.71(d,J=8.0Hz,1H), 7.85(s,1H), 6.86(d ,J=8.0Hz,1H),5.55(tdd,J=56.0, 6.4,3.2Hz,1H), 5.47(t,J=56.0,1H), 3.20(s,3H), 2.69–2.57(m,1H ),2.54– 2.47(m,1H),2.37(s,3H);

[0058]13C NMR(100MHz, CDCl3): δ179.2,143.2,134.3,128.9,125.3,122.5,115.3(t,J=238.2Hz),106.3,44.4(dd,J=4.2Hz,6.4Hz),39.9,26.3,21.8,18.3.

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Abstract

The invention discloses an electrochemical synthesis method of a 1,3-dimethyl-3-difluoroethyl-2-oxindole compound. The method comprises the following steps: by taking a hexafluoroisopropanol / water mixed solution containing difluoroacetic acid, N-methyl-N-arylacrylamide and an iodized salt as an electrolyte, placing an anode and a cathode in the electrolyte, introducing direct current, and carryingout electrochemical reaction to obtain a 1,3-dimethyl-3-difluoroethyl-2-oxindole compound. The method has the advantages of mild reaction conditions, simple operation, environmental protection, easily available raw materials, excellent compatibility of substrate functional groups, high reaction yield and the like.

Description

Technical field[0001]The invention relates to an electrochemical synthesis method of 1,3-dimethyl-3-difluoroethyl-2-oxoindole compound, in particular to an iodized salt under the condition of no external oxidant and under the action of direct current. A method for catalyzing the oxidative decarboxylation and cyclization reaction of difluoroacetic acid and N-methyl-N-arylacrylamide to synthesize 1,3-dimethyl-3-difluoroethyl-2-oxyindole compound derivatives, belonging to The field of organic intermediate synthesis technology.Background technique[0002]2-Indole oxide is the core structure of a variety of natural products. It is widely present in biologically active natural products and synthetic drug molecules, and has important biological and pharmacological activities. 1,1-Difluoroethyl can effectively improve the metabolic stability and bioavailability of biologically active molecules. The development of new synthetic methods containing difluoroethyl compounds is of great significanc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C25B3/05C25B3/07C25B3/09C25B3/23
Inventor 王峥谭英姿王宗成
Owner HUNAN UNIV OF SCI & ENG
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