Thionyl Chloride → 2-(2-Chloromethyl-benzo[b]thiophen-6-yloxy)-thiazolo[4,5-b]pyridine

Participants

Reaction Conditions

Reaction Steps

To a cooled (0° C.) solution of [6-(thiazolo[4,5-b]pyridin-2-yloxy)-benzo[b]thiophen-2-yl]-methanol (0.13 g, 0.4 mmol) in DCM (5 mL) was added thionyl chloride (30 μL, 49 mg, 0.4 mmol) and the reaction mixture was stirred (0° C., 3 h). The reaction mixture was partitioned between DCM (20 mL) and saturated NaHCO3 (10 mL). The organic layer was separated and the aqueous layer was extracted with DCM (2×20 mL). The organic layer was dried, filtered and concentrated in vacuo to provide the title compound as a yellow solid (0.11 g, 77%). MS (ESI): mass calcd. for C15H9ClN2OS2, 332.0; m/z found, 333.0 [M+H]+. 1H NMR (400 MHz, CDCl3): 8.57 (dd, J=4.8, 1.6, 1H), 8.07-7.91 (m, 2H), 7.77 (d, J=8.7, 1H), 7.40 (dd, J=8.7, 2.2, 1H), 7.31 (d, J=0.4, 1H), 7.25-7.14 (m, 1H), 4.86 (s, 2H).

Provenance & Evidence