Sodium hydride → 2,3,4,5-Tetrahydro-5-methyl-2-[[1-(triphenylmethyl)-1H-imidazol-4-yl]methyl]-1H-pyrido[4,3-b]indol-1-one

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Reaction Steps

A mixture of 2,3,4,5-tetrahydro-5-methyl-1H-pyrido[4,3-b]indol-1-one (0.3 g) and sodium hydride (80% dispersion in oil; 0.05 g) in dry DMF (5 ml) was stirred under nitrogen at 50° until hydrogen evolution ceased (ca. 0.5 h). The mixture was cooled to 40° and a solution of 4-(chloromethyl)-1-(triphenylmethyl)-1H-imidazole (0.53 g) in dry THF (3 ml) was added. The mixture was stirred at 40° to 23° over 2 h, poured into water (100 ml) and extracted with dichloromethane (3×100 ml). The dried organic phase was evaporated to give a semi-solid which was purified by FCC eluting with dichloromethane:ethyl acetate:triethylamine (50:50:1) to give a solid. This was slurried in hexane and filtered to give the title compound (0.37 g), m.p. 205°-210° (decomp.).

Provenance & Evidence