Potassium Carbonate → N,N-Dimethyl-2-(6-nitro-1H-indazol-1-yl)ethan-1-amine

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-nitroindazole (2 g, 12 mmol) and potassium carbonate (5.1 g 37 mmol) in DMF (40 mL) for 30 minutes, followed by the addition of 2-(dimethylamino)ethylchloride hydrochloride (2.65 g 18.4 mmol) was added. The mixture was heated to 60° C. for 6 hours, cooled to room temperature, 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 (1.8 g, 64% yield). 1H NMR (300 MHz, DMSO-d6) ppm 2.16 (s, 6H), 2.73 (t, J=6.44, 2H), 4.66 (t, J=6.44, 2H), 7.94 (m, 1H), 8.00 (m, 1H), 8.31 (m, 1H), 8.79 (m, 1H); MS (DCI/NH3) m/z 235 [M+H]+.

Provenance & Evidence