N-Iodosuccinimide → 2-(4-Fluoro-phenoxy)-5-iodo-imidazo[2,1-b][1,3,4]thiadiazole

Participants

Reaction Steps

2-(4-Fluoro-phenoxy)-imidazo[2,1-b][1,3,4]thiadiazole (0.6 g, 2.55 mmol) was dissolved in N,N-dimethylformamide (10 mL) and N-iodosuccinimide (0.63 g, 2.81 mmol) was added in one portion. The reaction mixture was stirred at room temperature overnight in the absence of light. The yellow suspension was filtered and rinsed with diethylether (2×2 mL) to give 2-(4-fluoro-phenoxy)-5-iodo-imidazo[2,1-b][1,3,4]thiadiazole as a white solid (0.65 g, 71%). The filtrate was evaporated and the residue was triturated with diethylether (6 mL) and filtered. This solid was purified by column chromatography (Biotage™/Flash, silica, methanol:dichloromethane 0:10 to 1:9) to give 2-(4-fluoro-phenoxy)-5-iodo-imidazo[2,1-b][1,3,4]thiadiazole as a white solid (0.15 g, 16% yield).

Provenance & Evidence