Thionyl Chloride → 2-(2-Chloroethyl)imidazo[1,2-A]pyridine

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Reaction Steps

A mixture of 2-(imidazo[1,2-a]pyridin-2-yl)ethanol (400 mg, 2.466 mmol) from Example a4) and SOCl2 (2 mL, 27.4 mmol) in DCM (10 mL) was stirred at room temperature for 2 days. The mixture was concentrated in vacuo. The residue was diluted with EtOAc (3×100 mL) and washed with saturated NaHCO3 solution (6 mL×4) and brine (6 mL). The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by Pre-TLC (PE/EA=1/1, v/v) to give the title compound as an oil (300 mg, yield 70%).

Provenance & Evidence