1-Hydroxybenzotriazole → N-(4-methyl-3-(pyrimidin-5-yl)-phenyl)-9H-carbazole-1-carboxamide

Participants

Reaction Steps

To a suspension of 9H-carbazole-1-carboxylic acid (148 mg) and 1-hydroxybenzotriazole (130 mg) in dichloromethane (3 ml) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (201 mg) and the mixture was stirred for 5 minutes. After adding 4-methyl-3-(pyrimidin-5-yl)aniline (130 mg) and 4-dimethylaminopyridine (128 mg), the mixture was stirred for 24 hours. The mixture was diluted with dichloromethane and washed with water and brine. The organic layer was dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by a silica gel column chromatography eluting with 2% methanol in dichloromethane to give N-(4-methyl-3-(pyrimidin-5-yl)-phenyl)-9H-carbazole-1-carboxamide (140 mg, 52.8%).

Provenance & Evidence