Potassium Phosphate, Tribasic → HCID 89648401, compound

Participants

Reaction Conditions

Reaction Steps

1.0 g ethyl 1-(4-bromo-2,6-difluorobenzyl)-5-cyclopropyl-4-methyl-1H-pyrazole-3-carboxylate (2.51 mmol, 1.0 eq.) were dissolved in 40 mL toluene and 0.280 g cyclopropylboronic acid (3.26 mmol, 1.3 eq.), 1.86 g potassium phosphate (8.77 mmol, 3.5 eq.), 70 mg tricyclohexylphosphine (0.25 mmol, 0.10 eq.) and 0.66 mL water were added. The reaction mixture was flushed with nitrogen and 28 mg palladium acetate (0.125 mmol, 0.050 eq.) were added. The reaction mixture was stirred at 100° C. over night. Again 0.280 g cyclopropylboronic acid (3.26 mmol, 1.3 eq.), 1.86 g potassium phosphate (8.77 mmol, 3.5 eq.), 70 mg tricyclohexylphosphine (0.25 mmol, 0.10 eq.) and 0.66 mL water were added. The reaction mixture was flushed with nitrogen and 28 mg palladium acetate (0.125 mmol, 0.050 eq.) were added. The reaction mixture was stirred at 100° C. over night. Water was added and the aqueous phase was washed with ethyl acetate twice. The combined organic layers were dried over a silicon filter and concentrated in vacuo. The crude product was purified by flash chromatography to provide 652 mg (1.63 mmol, 65%) of the analytically pure target compound.

Provenance & Evidence