Sodium hydride → HCID 69670931, compound

Participants

Reaction Steps

To a solution of 5-methoxy-2-phenylindole (73.0 mg) in N,N-dimethylformamide (1.6 mL) was added sodium hydride (dispersed in liquid paraffin, minimum 55%, 22 mg) under cooling with ice, and the mixture was stirred at room temperature for 70 minutes. Then methyl 3-(bromomethyl)benzoate (89.9 mg) was added, and the mixture was stirred at 100° C. for 6 hours. The reaction mixture was cooled to room temperature. Saturated ammonium chloride-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 (eluting solvent: ethyl acetate-hexane) to obtain the title compound (50.6 mg).

Provenance & Evidence