Potassium Carbonate → HCID 46841560, compound

Participants

Reaction Steps

3-(4-sec-butylphenyl)-2-(6-chloropyridin-3-yl)quinazolin-4(3H)-one (0.345 g, 0.89 mmol), trimethyboroxine (0.124 mL, 0.89 mmol), Pd(PPh3)4 (0.102 g, 0.09 mmol), and K2CO3 (0.368 g, 2.67 mmol) were combined in dioxane (10 mL) and heated at reflux under nitrogen for 5 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 50% ethyl acetate/heptane to 100% ethyl acetate, to afford the title compound as a white solid (0.195 g, 59%). 1H-NMR (300 MHz, DMSO-6): δ 8.43 (d, J=2.0 Hz, 1H), 8.20 (d, J=6.9 Hz, 1H), 7.89-7.94 (m, 1H), 7.79 (d, J=7.9 Hz, 1H), 7.55-7.65 (m, 2H), 7.13-7.27 (m, 4H), 7.07 (d, J=8.1 Hz, 1H), 2.55-2.60 (m, 1H), 2.36 (s, 3H), 1.37-1.58 (m, 2H), 1.15 (d, J=6.9 Hz, 3H), 0.66 (t, J=7.3 Hz, 3H). MS (APCI) m/z: 370 (M+H)+.

Provenance & Evidence