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

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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, 4-(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) were stirred at 80° C. for 6 hours. The reaction mixture was concentrated under reduced pressure and then extracted with ethyl acetate. The extract 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 55.5 mg of the titled compound as a pale yellow liquid.

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