Sodium Carbonate → 1-(2-chloro-phenyl)-5-(2'-methylsulfanyl-biphenyl-4-yl)-3-pentafluoroethyl-4,5-dihydro-1H-pyrazole

Participants

Reaction Steps

A solution of 5-(4-bromo-phenyl)-1-(2-chloro-phenyl)-3-pentafluoroethyl-4,5-dihydro-1H-pyrazole (100.0 mg, 0.19 mmol) prepared in Step 3 of Preparation 1, 2-(methylthio)phenylboronic acid (80.0 mg, 0.28 mmol), Pd(PPh3)4 (26 mg, cat.), and a 2N sodium carbonate solution (0.6 mL) in N,N-dimethylformamide (5 mL) was stirred at 80° C. for 6 hours. The reaction mixture was concentrated under reduced pressure and then diluted with ethyl acetate. The organic layer was washed with distilled water, dried on anhydrous magnesium sulfate, and then concentrated under reduced pressure to give a yellow liquid residue. The resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/20) to give 54.0 mg of 1-(2-chloro-phenyl)-5-(2′-methylsulfanyl-biphenyl-4-yl)-3-pentafluoroethyl-4,5-dihydro-1H-pyrazole as a pale yellow liquid.

Provenance & Evidence