Methyl iodide → 1-Methyl-1H-indole-4-carbonitrile

Participants

Reaction Steps

Add slowly a solution of indole-4-carbonitrile (1.0 g, 7.04 mmol) in anhydrous DMF (5 mL) to a suspension of sodium hydride (60% dispersion in mineral oil, 0.6 g, 8.64 mmol) in anhydrous DMF (2 mL) at 0° C. and warm the reaction mixture to ambient temperature. Add iodomethane (0.7 mL, 10.6 mmol) and stir the reaction for 1 h at ambient temperature. Dilute the reaction mixture with 1M aqueous NH4OH (30 mL) and extract with diethyl ether (3×10 mL). Combine the organic extracts, dry over anhydrous Na2SO4, concentrate in vacuo and purify by chromatography on silica gel eluting with hexane/EtOAc (1:0, 9:1, 4:1 and 7:3) to obtain the desired intermediate as a yellow oil (1.0 g, 87%). GC-MS m/z: 156 (M+).

Provenance & Evidence