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

Participants

Reaction Steps

To a solution of 5-methoxyindole (200 mg, 1.36 mmol) in 1.5 mL of dry N,N-dimethylformamide was added sodium hydride (55%, 66 mg, 1.5 mmol) at 0° C. After the reaction mixture was stirred at the same temperature for 30 min, methyl iodide (0.10 mL, 1.6 mmol) was added with additional stirring at room temperature overnight. After the reaction mixture was quenched with water (5 mL) at 0° C., the solution was extracted with diethyl ether (20 mL) twice. The combined extracts were washed with brine (5 mL), and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5 to 80/20) to obtain 5-methoxy-1-methylindole (182 mg, 83%).

Provenance & Evidence