Tributylamine → HCID 178437917, compound

Participants

Reaction Conditions

Reaction Steps

Into a 100-mL 3-necked round-bottom flask, was placed a solution of 3-ethyl-1-phenyl-1H-indazol-6-amine hydrochloride (300 mg, 1.10 mmol, 1.00 equiv) in N,N-dimethylformamide (30 mL), tributylamine (492 mg, 2.66 mmol, 2.50 equiv), 1H-benzo[d]imidazole-5-carboxylic acid (180 mg, 1.11 mmol, 1.00 equiv), 2-chloro-1-methylpyridinium iodide (330 mg, 1.29 mmol, 1.20 equiv). The resulting solution was stirred for 2 days at 100° C. in an oil bath. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with dichloromethane/methanol (50:1). The resulting mixture was diluted with methanol (10 mL) and the solids were washed with diethyl ether (1×50 mL) to yield N-(3-ethyl-1-phenyl-1H-indazol-6-yl)-1H-benzo[d]imidazole-5-carboxamide as a yellow solid.

Provenance & Evidence