Sodium hydride → 1-(3-Benzyloxybenzyl)-5-methoxy-2-phenylindole

Participants

Reaction Steps

To a solution of 5-methoxy-2-phenylindole (245 mg) in N,N-dimethylformamide (4.5 mL) was added sodium hydride (dispersed in liquid paraffin, minimum 55%, 72 mg) under cooling with ice, and the mixture was stirred at room temperature for 75 minutes. Then a solution of 3-(benzyloxy)benzyl bromide (365 mg) in N,N-dimethylformamide (1 mL) was added dropwise, and the mixture was stirred at 80° C. for 15 hours. The reaction mixture was cooled to room temperature. A saturated aqueous ammonium chloride solution-water (2/1) were added and this resulting mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by aminopropylated silica gel column chromatography to obtain the title compound (202 mg).

Provenance & Evidence