1-Methylindole → HCID 18985206, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 0.27 g (1.05 mmol) of N,N-diethyl 4,5,6,7-tetrahydrobenzimidazole-5-carboxamide hydrochloride, 0.16 ml (1.25 mmol) of 1-methylindole, and 0.15 ml (1.65 mmol) of phosphorus oxychloride was heated at 80° C. for 2 hours while stirring. 30 ml of water were added thereto, and the mixture was rendered basic with a 1N sodium hydroxide aqueous solution, followed by extracting with ethyl acetate. The ethyl acetate layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was distilled under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: dichloromethane/methanol/aqueous ammonia=10:1:0.1 by volume) and preparative thin layer chromatography (developing solvent: dichloromethane/methanol/aqueous ammonia=10:1:0.1 by volume) to obtain 20 mg of a foaming substance. To the product was added 10 mg of fumaric acid to convert it to a fumarate. Recrystallization from ethyl acetate/methanol (10:1 by volume) gave 10 mg of 5-[(1-methylindol-3-yl)carbonyl]-4,5,6,7-tetrahydrobenzimidazole fumarate.

Provenance & Evidence