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3-trifluoromethyl substituted pyrazole derivative and synthesis method thereof

A technology of pyrazole derivatives and trifluoromethyl, applied in the field of 3-trifluoromethyl substituted pyrazole derivatives and synthesis thereof, can solve problems such as unfavorable amplification synthesis, achieve good industrial application prospects, efficient synthesis methods, The effect of high product yield

Active Publication Date: 2019-12-20
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, highly active gaseous 2,2,2-trifluorodiazoethane is explosive, and requires in-situ generation and use of excess transition metals or flow chemistry strategies to promote the reaction, which is not conducive to scale-up synthesis

Method used

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  • 3-trifluoromethyl substituted pyrazole derivative and synthesis method thereof
  • 3-trifluoromethyl substituted pyrazole derivative and synthesis method thereof
  • 3-trifluoromethyl substituted pyrazole derivative and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] This example provides a 3-trifluoromethyl-substituted pyrazole derivative and a preparation method thereof.

[0058] Its preparation method is as follows: in an air atmosphere, in a 25 ml reaction flask equipped with a reflux condenser, add 1 mmol of benzaldehyde, 1.2 mmol of p-toluenesulfonyl hydrazide, 6 ml of toluene, 3 mmol of 1,8- Diazabicycloundec-7-ene, 2 mmol 2-bromo-3,3,3-trifluoropropene, the reaction system was stirred and reacted at 60°C for 6 hours, the heating and stirring were stopped, and water, ethyl acetate Ester extraction reaction solution, the ethyl acetate layer is subjected to vacuum rotary evaporation, solvent removal, and then separated and purified by column chromatography to obtain the target product, the column chromatography eluent used is petroleum ether and ethyl acetate, and the volume ratio is 10:1; the yield of product was 88%.

Embodiment 2

[0060] This example provides a 3-trifluoromethyl-substituted pyrazole derivative and a preparation method thereof.

[0061] Its preparation method is as follows: in an air atmosphere, in a 25 ml reaction flask equipped with a reflux condenser, add 1 mmol of benzaldehyde, 1.2 mmol of benzenesulfonyl hydrazide, 6 ml of toluene, 3 mmol of 1,8-bis Azabicycloundec-7-ene, 2 mmol 2-bromo-3,3,3-trifluoropropene, the reaction system was stirred and reacted at 60°C for 6 hours, stopped heating and stirring, added water, ethyl acetate The reaction solution was extracted, the ethyl acetate layer was rotary evaporated under reduced pressure, the solvent was removed, and then separated and purified by column chromatography to obtain the target product. The eluent of the column chromatography used was petroleum ether and ethyl acetate, and the volume ratio was 10 : 1; The productive rate of product is 77%.

Embodiment 3

[0063] This example provides a 3-trifluoromethyl-substituted pyrazole derivative and a preparation method thereof.

[0064] Its preparation method is as follows: in an air atmosphere, in a 25 ml reaction flask equipped with a reflux condenser, add 1 mmol of benzaldehyde, 1.2 mmol of p-toluenesulfonyl hydrazide, 6 ml of toluene, 3 mmol of lithium tert-butoxide , 2 mmoles of 2-bromo-3,3,3-trifluoropropene, the reaction system was stirred at 60°C for 1 hour, the heating and stirring were stopped, water was added, the reaction liquid was extracted with ethyl acetate, and the ethyl acetate layer was reduced Press rotary steaming, remove the solvent, and then separate and purify by column chromatography to obtain the target product. The column chromatography eluent used is petroleum ether and ethyl acetate, and the volume ratio is 10:1; the yield of the product is 24%.

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Abstract

The invention belongs to the technical field of medical material synthesis, and particularly relates to a 3-trifluoromethyl substituted pyrazole derivative and a synthesis method thereof. The derivative is prepared by mixing an aldehyde, sulfonyl hydrazide, 2-bromo-3,3,3-trifluoropropene, an alkali and an organic solvent I for reacting, or mixing a hydrazone, 2-bromo-3,3,3-trifluoropropene, an alkali and the organic solvent I for reacting. The method has high efficiency, the reaction has good adaptability to functional groups and wide adaptability to substrates, and the product yield is high.The raw materials are cheap and easily available, and the method can be amplified to 10g-level large-scale production or larger-scale production. The method is simple and safe to operate, and mild inreaction conditions. The obtained product comprises key intermediates for constructing COX-2 inhibitor Colecoxib and Mavacoxib, lung cancer inhibitor SC-560 and measles virus inhibitor AS-136, has wide applications in the fields of pesticides, medicines and materials, and has a good industrial application prospect.

Description

technical field [0001] The invention belongs to the technical field of medical material synthesis, and in particular relates to a 3-trifluoromethyl-substituted pyrazole derivative and its synthesis method and application. Background technique [0002] 3-trifluoromethyl-substituted pyrazole derivatives have important application value in the fields of materials and medicine, such as COX-2 inhibitors Colecoxib and Mavacoxib, lung cancer inhibitor SC-560, drug DPC-602 for the treatment of arterial thrombotic diseases, measles virus Inhibitor AS-136A, anticoagulant Razaxaban, insecticide DP-23, etc. all contain 3-trifluoromethyl substituted pyrazole skeleton structure ( figure 1 ) (Eur. J. Org. Chem. 2017, 6566). The traditional synthesis method of this kind of compound mainly utilizes the dehydration condensation cyclization reaction of hydrazine compound and 1,3-dicarbonyl compound or acetylene compound, but this strategy is often accompanied by regioselective isomers (5-tri ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D231/12C07D401/04C07D405/04
CPCC07D231/12C07D401/04C07D405/04
Inventor 竺传乐曾浩江焕峰
Owner SOUTH CHINA UNIV OF TECH
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