Iodoethane → 1-ethyl-6-methoxy-1H-indole-3-carbonitrile

Participants

Reaction Steps

To a solution of 6-methoxy-1H-indole-3-carbonitrile (9.9 g, 57.6 mmol) in DMF (150 mL) was added NaH (60% dispersion in mineral oil, 3.45 g, 86.3 mmol). The reaction mixture was stirred for 15 min and then ethyl iodide (5.53 mL, 69.1 mmol) was added and the mixture was stirred at room temperature overnight. The reaction mixture was then diluted with H2O and extracted with EtOAc (2×). The organic phases were washed with H2O (3×) and saturated NaCl and then dried and concentrated to a semi-solid. The crude product was purified via column chromatography on silica gel (200 g) using CH2Cl2/hexanes (50-100%) as eluent to yield 6-methoxy-1-ethyl-1H-indole-3-carbonitrile as a tan solid.

Provenance & Evidence