Hydrochloric Acid → HCID 77230603, compound

Participants

Reaction Steps

Sodium hydroxide (100 mL; 5.0 M; 500 mmol; 18.1 eq.) was added in one portion to a solution of methyl 3-ethynyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-5-carboxylate (7.9 g; 27.7 mmol; 1.0 eq.) in DMF (100 mL) and MeOH (100 mL). The reaction mixture was stirred at RT for 1 h, then poured into a 1N HCl solution (pH 1) and extracted with DCM. Combined organic phases were washed with brine, dried over magnesium sulfate, filtered and concentrated. The brown solid obtained was triturated with MeOH to give the title compound as a red solid (4.83 g, 65%). 1H NMR (300 MHz, DMSO-d6) δ 13.09 (s, 1H), 8.35-8.28 (m, 1H), 8.04 (dd, J=8.9, 1.5 Hz, 1H), 7.90 (dd, J=8.9, 0.6 Hz, 1H), 5.95 (dd, J=9.5, 2.3 Hz, 1H), 4.73 (s, 1H), 3.94-3.84 (m, 1H), 3.83-3.69 (m, 1H), 2.43-2.27 (m, 1H), 2.09-1.93 (m, 2H), 1.83-1.65 (m, 1H), 1.64-1.52 (m, 2H). HPLC (max plot) 99.5%; Rt %3.17 min. UPLC/MS: (MS−) 269.3.

Provenance & Evidence