Synthesis method of 3, 5-diaryl-4-trifluoromethyl pyrazole derivative

A technology of trifluoromethylpyrazole and a synthesis method, applied in 3 fields, can solve the problems of low metal catalysis economy, troubled multi-step reaction, complicated operation and the like

Active Publication Date: 2021-09-10
WENZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

As for the synthesis of 4-trifluoromethylpyrazole compounds, there are few reports. Only Tsui’s research group reported that alkyne aldehyde or acetylene ketone was used as the reaction substrate. Next, self-cyclization generates 4-trifluoromethylpyrazole compound ( Org. Lett. 2017, 19 , 658-661)
The above methods have the problems of multi-step reaction, cumbersome operation, and low economic efficiency of metal catalysis.

Method used

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  • Synthesis method of 3, 5-diaryl-4-trifluoromethyl pyrazole derivative
  • Synthesis method of 3, 5-diaryl-4-trifluoromethyl pyrazole derivative
  • Synthesis method of 3, 5-diaryl-4-trifluoromethyl pyrazole derivative

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specific Embodiment 1

[0023] Specific example one: 41.2 mg (0.2 mmol) 2-chloro-3,3,3-trifluorophenylpropene, 65.8 mg (0.24 mmol) benzaldehyde p-toluenesulfonyl hydrazone, 67.3 mg (0.6 mmol) tert-butanol Potassium was added to 3 ml of solvent tetrahydrofuran. The reaction was stirred at 70 °C for 12 hours. Cool after the reaction, filter the reaction solution to obtain the filtrate and wash it with saturated sodium chloride solution, extract it with ethyl acetate and dry it with anhydrous magnesium sulfate, and use a rotary evaporator to remove the solvent from the filtrate to obtain a residue, and pass the residue through a silica gel column with The eluent prepared by petroleum ether and ethyl acetate at a volume ratio of 10:1 was used for eluting, the effluent was collected according to the actual gradient, and detected by TLC, the effluent containing the target product was combined, and the combined effluent was used with a rotary evaporator The solvent was removed by rotation, and dried in vac...

specific Embodiment 2

[0024] Specific example two: 44 mg (0.2 mmol) 1-(2-chloro-3,3,3-trifluoro-1-propenyl)-4-toluene, 65.8 mg (0.24 mmol) benzaldehyde p-toluenesulfonyl Hydrazone, 67.3 mg (0.6 mmol) of potassium tert-butoxide, was added to 3 ml of solvent tetrahydrofuran. The reaction was stirred at 70 °C for 12 hours. Cool after the reaction, filter the reaction solution to obtain the filtrate and wash it with saturated sodium chloride solution, extract it with ethyl acetate and dry it with anhydrous magnesium sulfate, and use a rotary evaporator to remove the solvent from the filtrate to obtain a residue, and pass the residue through a silica gel column with The eluent prepared by petroleum ether and ethyl acetate at a volume ratio of 10:1 was used for eluting, the effluent was collected according to the actual gradient, and detected by TLC, the effluent containing the target product was combined, and the combined effluent was used with a rotary evaporator The solvent was removed by rotation an...

specific Embodiment 3

[0025] Specific example three: 44 mg (0.2 mmol) 1-(2-chloro-3,3,3-trifluoro-1-propenyl)-2-methylbenzene, 65.8 mg (0.24 mmol) benzaldehyde p-toluene Sulfonylhydrazone, 67.3 mg (0.6 mmol) of potassium tert-butoxide, was added to 3 ml of solvent tetrahydrofuran. The reaction was stirred at 70 °C for 12 hours. Cool after the reaction, filter the reaction solution to obtain the filtrate and wash it with saturated sodium chloride solution, extract it with ethyl acetate and dry it with anhydrous magnesium sulfate, and use a rotary evaporator to remove the solvent from the filtrate to obtain a residue, and pass the residue through a silica gel column with The eluent prepared by petroleum ether and ethyl acetate at a volume ratio of 10:1 was used for eluting, the effluent was collected according to the actual gradient, and detected by TLC, the effluent containing the target product was combined, and the combined effluent was used with a rotary evaporator The solvent was removed by rot...

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Abstract

The invention relates to a synthesis method of a 3, 5-diaryl-4-trifluoromethyl pyrazole derivative, which comprises the following step of: by taking aromatic aldehyde p-toluenesulfonyl hydrazone and 2-chloro-3, 3, 3-trifluoroaryl propylene as reaction substrates, potassium tert-butoxide as alkali and tetrahydrofuran as a solvent, stirring and reacting for 12 hours at 70 DEG C. The method has the advantages of simple and easily available raw materials, relatively mild reaction conditions, wide substrate universality, novel preparation process, less pollution, low energy consumption and the like.

Description

technical field [0001] The invention relates to a preparation method of 3,5-diaryl-4-trifluoromethylpyrazole derivatives. Background technique [0002] Pyrazole is an important five-membered heterocyclic ring containing N atoms, pyrazole derivatives are also an important class of heterocyclic compounds, and fluorine-containing pyrazole compounds are especially widely used in natural products, drugs and drug intermediates, pesticides In the synthesis of materials, dyes, especially, fluorine-containing pyrazole compounds are important motifs in biologically active compounds, so they have very important application research value. For example, SC-560 as a lung cancer inhibitor, Celecoxib and Mavacoxib as COX-2 inhibitors ( Angew. Chem. Int. Ed . 2017, 56 , 8823-8827), DPC-602 can prevent arterial thrombosis, AS-136A is a measles virus inhibitor, Razaxaban acts as an anticoagulant, DP-23 has insecticidal activity ( Org. Lett . 2020, 22 (3), 809-813). Therefore, the develop...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D231/12
CPCC07D231/12
Inventor 张兴国侯沁伶涂海勇张小红
Owner WENZHOU UNIVERSITY
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