Phosphorus oxychloride → HCID 86669008, compound

Participants

Reaction Steps

A stirred solution of 2-(2-chloro-6-fluorophenyl)-7-fluorothiazolo[5,4-c]pyridine 5-oxide (3.0 g, 10.5 mmol) in phosphoryl chloride (50 mL) was heated at 110° C. for 45 minutes. After cooling to room temperature, the volatiles were removed under reduced pressure and the resultant residue was partitioned between a potassium carbonate saturated solution (100 mL) and EtOAc (50 mL). The aqueous phase was extracted with EtOAc (2×50 mL) and the combined organic layers were washed with water (100 mL), dried and concentrated under reduced pressure. The resultant residue was purified by column chromatography on silica gel eluting with 10% diethyl ether in pentane to afford the title compound as a colourless solid (0.71 g, 22% yield). 1H NMR (400 MHz, CDCl3): δ 8.38 (s, 1H), 7.56-7.46 (m, 1H), 7.41 (d, J=8.2 Hz, 1H), 7.21 (t, J=8.6 Hz, 1H).

Provenance & Evidence