Dichloromethane → HCID 178522779, compound

Participants

Reaction Steps

To a mixture of 3-bromo-6-carboxyindazole (5.84 g), cyclopentylmethylamine (3.48 ml), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (3.25 g), methylene chloride (120 ml) and dimethylformamide (40 ml) was added 4-dimethylaminopyridine (5.10 g). After stirring for 48 hours, the reaction mixture was added to 450 ml ethyl acetate; washed with 1N hydrochloric acid, 0.5M sodium carbonate and brine: dried (MgSO4); and evaporated. The residue was flash chromatographed over 175 g silica gel, eluting sequentially with methylene chloride (350 ml), 15:85 ethyl acetate:methylene chloride (350 ml), and 1:3 ethyl acetate:methylene chloride to afford 3-bromo-6-(N-cyclopentylmethylcarbamoyl)indazole as a light red solid (5.6 g, 72%), mp 119°-125°.

Provenance & Evidence