Potassium Carbonate → 3-chloro-5-nitro-1-(2-pyrrolidin-1-yl-ethyl)-1H-indazole

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

A mixture of 3-chloro-5-nitro-1H-indazole (1.5 g, 7.6 mmol) was treated with potassium carbonate (3.1 g, 23 mmol) in DMF (20 mL) for 30 minutes, after which 1-(2-chloro-ethyl)-pyrrolidine (1.9 g, 11 mmol) was added. The mixture was heated to 50° 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. 1H NMR (300 MHz, DMSO-d6) ppm 1.60 (m, 4H), 2.45 (m, 4H), 2.89 (t, J=6.44, 2H), 4.58 (t, J=6.44, 2H), 8.00 (m, 1H), 8.30 (m, 1H), 8.60 (m, 1H); MS (DCI/NH3) m/z 295 [M+H]+.

Herkunft & Nachweise