Potassium Phosphate, Tribasic → HCID 89826224, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 300 mg (0.68 mmol) of N-(2-bromo-5-fluorobenzyl)-5-chloro-N-cyclopropyl-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide in a 10/1 mixture of toluene/water degassed with argon, are successively added 190 mg (1.50 mmol) of cyclohex-1-en-ylboronic acid, 38 mg (0.137 mmol) of tricyclohexylphosphine, 15 mg (0.069 mmol) of palladium (II) acetate and 437 mg (2.06 mmol) of tri-potassium phosphate. The mixture is heated at 100° C. for 1 hour. The reaction mixture is cooled to ambient temperature. 1 mL of water is added to the reaction mixture and the organic phase is filtered over a cake of diatomaceous earth. The cake is washed twice by dichloromethane and the combined organic phases are concentrated under vacuum to give 516 mg of crude material. A purification by column chromatography on silica gel (gradient heptane/ethyl acetate) yields 154 mg (49% yield) of 5-chloro-N-[2-(cyclohex-1-en-1-yl)-5-fluorobenzyl]-N-cyclopropyl-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide: (M+H)=438.

Provenance & Evidence