Potassium Carbonate → HCID 46841561, compound

Participants

Reaction Steps

3-(4-chlorophenyl)-2-(6-chloropyridin-3-yl)quinazolin-4(3H)-one (0.200 g, 0.54 mmol), trimethyboroxine (0.076 mL, 0.54 mmol), Pd(PPh3)4 (0.063 g, 0.05 mmol), and K2CO3 (0.224 g, 1.62 mmol) were combined in dioxane (10 mL) and heated at reflux under nitrogen for 5 hours. Additional Pd(PPh3)4 (50 mg) and trimethylboroxine (0.200 mL) were added and reflux was continued for 28 hours. The reaction mixture was cooled to room temperature, filtered through Celite®, with THF washings, concentrated, and purified by flash chromatography on silica gel, eluting with 40% ethyl acetate/heptane to 100% ethyl acetate. Further purification by reverse-phase HPLC, eluting with 10% to 90% CH3CN in water with 0.1% TFA, afforded the title compound as a white solid (0.025 g, 13%). 1H-NMR (300 MHz, DMSO-6): δ 8.46 (d, J=2.0 Hz, 1H), 8.21 (d, J=7.0 Hz, 1H), 7.90-7.95 (m, 1H), 7.79 (d, J=7.9 Hz, 1H), 7.60-7.65 (m, 2H), 7.42-7.46 (m, 4H), 7.16 (d, J=8.1 Hz, 1H), 2.41 (s, 3H). MS (APCI) m/z: 348 (M+H)+.

Provenance & Evidence