Potassium Sodium Tartrate → [6-(Thiazolo[4,5-b]pyridin-2-yloxy)-benzo[b]thiophen-2-yl]-methanol

Participants

Reaction Conditions

Reaction Steps

To a cooled (0° C.) solution of 6-(thiazolo[4,5-b]pyridin-2-yloxy)-benzo[b]thiophene-2-carboxylic acid methyl ester (0.18 g, 0.5 mmol) in DCM (5 mL) was added LAH (2 M in THF, 0.3 mL, 0.3 g, 0.5 mmol) and the reaction mixture was stirred (0° C., 1 h). The reaction mixture was treated with saturated aqueous Rochelle's salt (2 mL) and partitioned with EtOAc (15 mL). The organic layer was separated and the aqueous layer was extracted with EtOAc (2×15 mL). The organic layer was dried, filtered and concentrated in vacuo to provide the title compound as an orange solid (0.13 mg, 82%). MS (ESI): mass calcd. for C15H10O2S2, 314.0; m/z found, 315.0 [M+H]+. 1H NMR (400 MHz, CDCl3): 8.57 (dd, J=4.8, 1.7, 1H), 8.02 (dd, J=7.9, 1.6, 1H), 7.95 (d, J=2.2, 1H), 7.76 (d, J=8.7, 1H), 7.38 (dd, J=8.6, 2.3, 1H), 7.21 (dd, J=7.9, 4.9, 2H), 4.94 (s, 2H), 2.14 (s, 1H).

Provenance & Evidence