Hexachloroethane → 2-(2-phenoxyquinolin-8-yl)oxazolo[4,5-c]pyridin-4(5H)-one

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Reaction Steps

A solution of triphenylphosphine (421 mg, 1.607 mmol), Et3N (597 μl, 4.29 mmol), and perchloroethane (317 mg, 1.339 mmol) in DCM (5357 μl) was stirred at RT for 5 min before a slurry of N-(2,4-dihydroxypyridin-3-yl)-2-phenoxyquinoline-8-carboxamide (200 mg, 0.536 mmol) in DCM (3 ml) was added to make a light yellow solution; this was stirred for 1 h at RT. The reaction mixture was then concentrated onto silica gel and chromatographically purified (silica gel, 100% DCM to 4% MeOH/DCM) to provide 2-(2-phenoxyquinolin-8-yl)oxazolo[4,5-c]pyridin-4(5H)-one (179, 38% yield over two steps) as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 6.46 (d, J=7.04 Hz, 1H) 7.22-7.30 (m, 2H) 7.36-7.47 (m, 5H) 7.55 (t, J=7.73 Hz, 1H) 7.95 (d, J=7.24 Hz, 1H) 8.22 (d, J=8.80 Hz, 1H) 8.64 (d, J=6.26 Hz, 1H) 12.51 (br. s., 1H). MS (ESI, pos. ion) m/z: 356.1 (M+1).

Provenance & Evidence