Methyl iodide → 1-methyl-1H-indole-5-carbonitrile

Participants

Reaction Steps

To a solution of 1H-indole-5-carbonitrile (600 mg, 4.2 mmol) in DMF (5 mL) at 0° C. was added NaH (201 mg, 60% in oil, 8.4 mmol) with vigorous stirring. The solution was stirred 30 min, then iodomethane (1.8 g, 12.6 mmol) was added. The reaction mixture was stirred at RT for 4 h. The reaction was quenched with water (50 mL) and extracted with EtOAc (3×100 mL). The organic layers were combined, dried (MgSO4), filtered, and concentrated under reduced pressure to afford 800 mg of 1-methyl-1H-indole-5-carbonitrile (294) as white solid: MS (ESI) m/z=157.3 [M+1]+.

Provenance & Evidence