Triphenylphosphine → 5-(2-Acetylthioethyl)imidazo[1,2-a]pyridine

Participants

Reaction Steps

To a solution of triphenyl phosphine (4.20 g) in tetrahydrofuran (30 ml) was added dropwise, at −15° C., diisopropyl azodicarboxylate (3.16 ml). The mixture was stirred for 10 minutes at the same temperature. To the reaction mixture were, then, added a solution of 2-(imidazo[1,2-a]pyridin-5-yl)ethanol (1.00 g) in dimethylformamide (20 ml) and thioacetic acid (1.14 ml). The reaction mixture was stirred for 0.5 hour at −15° C. and, then, for 20 hours at room temperature. The reaction mixture was concentrated, which was diluted with ethyl acetate and washed with water, a saturated aqueous solution of sodium hydrogencarbonate and, then, with a saturated aqueous saline solution, followed by drying over anhydrous magnesium sulfate and concentration. The concentrate was purified by means of a column chromatography (carrier: silica gel, developing solvent: ethyl acetate-hexane, 1:1) to afford the title compound (0.52 g).

Provenance & Evidence