Sodium hydride → tert-Butyl 4-{1-[2-(5-bromo-2,3-difluorophenyl)-1-(4-chlorophenyl)-2-oxoethyl]butyl}benzoate

Participants

Reaction Steps

To a suspension of NaH (60 wt % in mineral oil, 0.129 g, 3.23 mmol) in DMF (5 mL) at 0° C. was add a solution of the product from Step D (0.900 g, 2.15 mmol) in DMF (2 mL). The suspension was stirred for 30 minutes, then a solution of tert-butyl 4-(1-bromobutyl)benzoate (0.742 g, 2.37 mmol) in DMF (2 mL) was added. The mixture was stirred at 0° C. for two hours then diluted with saturated NaCl (aq, 50 mL), then the product was extracted with EtOAc (3×30 mL). The combined organic extracts were washed with water then saturated NaCl (aq), dried over MgSO4, filtered, then concentrated. The resulting residue was purified by silica gel chromatography eluting with 0-50% toluene/hexanes to afford racemic mixtures of both diastereomers of the title compound.

Provenance & Evidence