Phosphorus oxychloride → HCID 178515752, compound

Participants

Reaction Steps

5-(Benzyloxy)-3-(2-chlorophenyl)-1H-imidazo[4,5-b]pyridin-2(3H)-one (905 mg, 2.58 mmol) and POCl3 (1965 μl, 21.08 mmol) was heated in microwave at 100° C. for 1 h. The mixture was concentrated. The residue was dissolved in EtOAc and saturated NaHCO3. The organics were separated, washed with brine, dried over MgSO4, filtered, and concentrated. The residue was dissolved in DCM (2.5 mL) and H2SO4 (6 drops) was added. The mixture was stirred vigorously for 15 minutes. DCM was removed by gentle heating. The residue was dissolved in MeOH and purified by preparative HPLC to give the title compound (5.0 mg). LCMS m/z=280.2, [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 6.63 (d, J=8.6 Hz, 1H), 7.63 (dd, J1=7.6, J2=1.6 Hz, 1H), 7.66 (td, J1=7.6, J2=1.8 Hz, 1H), 7.79 (m, 2H), 7.98 (d, J=8.6 Hz, 1H), 11.10 (broad s, 1H).

Provenance & Evidence