Tetrahydrofuran → HCID 86672701, compound

Participants

Reaction Steps

Methyl 5-chloro-1-(2,2-dimethoxyethyl)-1H-indazole-7-carboxylate (733 mg, 2.5 mmol) from Step B above was refluxed in 2 N HCl (8 mL) and THF (8 mL) until the reaction was complete by TLC (3-5 h). After cooling to room temperature, the pH of the reaction mixture was adjusted to 8 with NaHCO3, then extracted with ethyl acetate. The organic layers were combined, dried (Na2SO4), filtered, concentrated and purified by column chromatography (silica gel, 1:1 ethyl acetate/hexanes) to afford methyl 5-chloro-1-(2-oxoethyl)-1H-indazole-7-carboxylate as an off-white solid (472 mg, 76%): 1H NMR (300 MHz, CDCl3) δ 9.77 (s, 1H), 8.10 (s, 1H), 8.05 (s, 1H), 7.94 (s, 1H), 5.60 (s, 2H), 4.03 (d, J=8.4 Hz, 1H), 3.93 (s, 3H); MS (ESI+) m/z 253 (M+H).

Provenance & Evidence