Methyl iodide → 3-(4-Cyano-2-methoxybenzyl)1-methyl-5-nitroindole

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Reaction Steps

Sodium hydride (60% w/w dispersion in mineral oil, 0.12 g.) was added to a stirred solution of 3-(4-cyano-2-methoxybenzyl)-5-nitroindole (0.85 g.) in dry N,N-dimethylformamide (10 ml.) under a nitrogen atmosphere. After about one hour, iodomethane (0.645 g.) was added dropwise, and stirring continued at ambient temperature for 5 hours. The mixture was poured onto saturated aqueous ammonium chloride solution, extracted with ethyl acetate (2×20 ml.), the extract washed with water, brine, dried (MgSO4) and evaporated. The residue was crystallized from acetonitrile to give 3-(4-cyano-2-methoxybenzyl)-1-methyl-5-nitroindole (0.72 g., 81%) as a yellow solid, m.p. 200°-201° C.; partial NMR (250 MHz, DMSO-d6) 3.82(s, 3H, NMe); 3.92(s,3H, OMe); 4.12(s,2H, ArCH2)

Provenance & Evidence