Phosphorus oxychloride → HCID 57708073, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-(3-fluorophenyl)-4-hydroxy-7-methyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one (2.15 g, 8.27 mmol) and phosphorous oxychloride (10.0 mL, 107 mmol) was heated at 90° C. in an oil bath for 2.5 h. The excess POCl3 was removed on the rotovap and the resulting orange residue was treated with ice and solid Na2CO3 with stirring, and extracted 3×100 mL with EtOAc. The combined EtOAc layers were washed with brine, dried over MgSO4 and concentrated. Purification of the resulting crude material on an ISCO (40 g column, eluting with a gradient of 25-60% EtOAc in Hexanes) provided the title compound as a yellow crystalline solid. MS (ESI, pos.ion) m/z: 278.1 (M+1).

Provenance & Evidence