Methanol → methyl 1-(2-hydroxyethyl)-1H-indazole-7-carboxylate

Participants

Reaction Steps

To a stirred solution of 2-fluoro-3-formylbenzoate (0.5 g, 2.8 mmol) in methanol (4 mL) was added 2-hydrazinoethanol (0.2 mL, 2.8 mmol) and the mixture was stirred at room temperature. After the starting material was consumed, the solution was transferred to a microwave tube and microwaved at 150° C. for 5 h. The crude reaction was diluted with ethyl acetate, washed with water, dried (Na2SO4), filtered, concentrated under reduced pressure and purified by column chromatography (silica gel, 0% to 50% ethyl acetate in hexanes) to afford methyl 1-(2-hydroxyethyl)-1H-indazole-7-carboxylate (0.6 g, 95%): 1H NMR (500 MHz, CDCl3) δ 8.04-8.02 (m, 1H), 8.00-7.98 (m, 1H), 7.95-7.93 (m, 1H), 4.87-4.80 (m, 2H), 4.14-4.10 (m, 2H), 3.99 (s, 3H); MS (ESI+) m/z 221 (M+H).

Provenance & Evidence