Sodium hydride → HCID 69671126, compound

Participants

Reaction Steps

To a solution of 5-methoxy-2-phenylindole (90.9 mg) in N,N-dimethylformamide (1.8 mL) was added sodium hydride (dispersed in liquid paraffin, minimum 55%, 18 mg) under cooling with ice and an argon atmosphere, and the mixture was stirred under cooling with ice for 5 minutes and then at room temperature for 15 minutes. Methyl 5-(bromomethyl)-2-fluorobenzoate (101 mg) was added at room temperature, and the mixture was stirred at 80° C. for 13 hours. The reaction mixture was poured into a saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic layer was washed with water and saturated saline, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (53.2 mg).

Provenance & Evidence