Morpholine → 1-(2,4-difluoro-phenyl)-5-(4-fluoro-3-morpholin-4-yl-phenyl)-3-pentafluoroethyl-4,5-dihydro-1H-pyrazole

Participants

Reaction Conditions

Reaction Steps

5-(3-Bromo-4-fluoro-phenyl)-1-(2,4-difluoro-phenyl)-3-pentafluoroethyl-4,5-dihydro-1H-pyrazole (30.0 mg, 0.06 mmol) prepared in Step 5 of Preparation 7, morpholine (7.0 uL, 0.08 mmol), Pd2(dba)3 (3.0 mg, cat.), BINAP (4.0 mg, cat.) and sodium t-butoxide (9.0 mg, 0.10 mmol) were added to toluene (1.0 mL). The reaction mixture was stirred at 100° C. for 7 hours and then filtered through celite pad. Ethyl acetate was added to the filtrate, which was washed with a saturated solution of sodium hydrogen carbonate and brine, 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=1/8) to give 15.0 mg of the titled compound as a yellow liquid.

Provenance & Evidence