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

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).

1. stirringThe reaction mixture was stirred for 0.5 hour at −15° C.
2. waitfor 20 hours at room temperature
3. concentrationThe reaction mixture was concentrated
4. additionwhich was diluted with ethyl acetate
5. washwashed with water
6. dry with materialby drying over anhydrous magnesium sulfate and concentration
7. customThe concentrate was purified by means of a column chromatography (carrier: silica gel, developing solvent: ethyl acetate-hexane, 1:1)

ORD record

ord-fa1c2b09ecd84dd68e876167968e491f

Source dataset

uspto-grants-2001_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06174877B1