Potassium Carbonate → 3-bromo-6-nitro-1-(2-pyrrolidin-1-yl-ethyl)-1H-indazole

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-bromo-6-nitro-1H-indazole (1.0 g, 4.1 mmol) and potassium carbonate (2.9 g 21 mmol) in DMF (20 mL) was stirred for 30 minutes after which 1-(2-chloro-ethyl)-pyrrolidine (1.8 g, 10 mmol) was added. The mixture was heated to 50° C. for 6 hours, cooled to room temperature and filtered through a plug of silica gel which was rinsed with triethylamine/ethyl acetate (1/4). The filtrate was concentrated under reduced pressure and purified by flash chromatography (silica gel, triethylamine/ethyl acetate 1/30) to provide the title compound (900 mg, 64%). 1H NMR (300 MHz, DMSO-d6) ppm 1.61 (m, 4H), 2.47 (m, 4H), 2.90 (t, 2H, J=6.44), 4.69 (t, J=6.44, 2H), 7.82 (m, 1H), 8.02 (m, 1H), 8.86 (m, 1H); MS (DCI/NH3) m/z 339 [M+H]+.

Provenance & Evidence