Lithium Hydroxide → HCID 66787093, compound

Participants

Reaction Steps

To a solution of 6-(thiazolo[4,5-b]pyridin-2-yloxy)-benzofuran-3-carboxylic acid ethyl ester (200 mg, 0.59 mmol) in THF (6 mL) was added 4 N LiOH (0.15 mL, 0.59 mmol). Two additional aliquots of 4 N LiOH (each 0.30 mL) were added over 2 h. The mixture was stirred (rt, 24 h). The reaction mixture was partially concentrated in vacuo. The remaining aqueous solution was purified by reverse phase HPLC to provide the title compound as a white solid (92 mg, 44%). MS (ESI): mass calcd. for C15H8N2O4S, 312.02; m/z found, 312.9 [M+H]+. 1H NMR (400 MHz, DMSO-d6): 8.78 (s, 1H), 8.53 (dd, J=4.8, 1.7, 1H), 8.43 (dd, J=8.0, 1.7, 1H), 8.09 (d, J=8.6, 1H), 8.04 (d, J=2.1, 1H), 7.56-7.50 (m, 1H), 7.41-7.32 (m, 1H). The remaining proton was not detected and is believed to be hidden in the solvent peak.

Provenance & Evidence