Sodium hydride → HCID 57809957, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 42 mg (0.31 mmol) of oxindole in 1 mL of DMF was added 10 mg (0.39 mmol) of 60% sodium hydride in mineral oil. After hydrogen evolution ceased, 50 mg (0.17 mmol) of 2-[2-(5-fluoro-2-methoxyphenyl)-2-methylpropyl]-2-trifluoromethyloxirane was added and the mixture was warmed to 75° C. The reaction was monitored by TLC (ethyl acetate-hexanes (15:85)). After 40 minutes, the mixture was cooled and diluted with saturated aqueous ammonium chloride and extracted with three 5 mL portions of ethyl acetate. The combined organic layers were washed with three 5 mL portions of brine, dried over magnesium sulfate, and concentrated in vacuo. The crude material was chromatographed on silica gel prep plates (2×1 mm, ethyl acetate-hexanes (15:85)). The material from the prep plate was recrystallized from dichloromethane-hexanes-ether to afford 14 mg of the title compound.

Provenance & Evidence