Toluene → HCID 86710184, compound

Participants

Reaction Conditions

Reaction Steps

To a 50 mL round bottom flask, 4-(7-bromo-2-chloroquinazolin-4-yl)morpholine (1.0 g, 0.0030 mol—Preparation 1), 3-aminophenylboronic acid pinacol ester (0.657 g, 0.0030 mol), sodium carbonate (0.635 g, 0.0060 mol), toluene (20 mL), ethanol (4 mL) and water (3 mL) were added. The reaction mixture was degassed with N2 for 5-10 minutes. To the same reaction mixture, Pd(PPh3)2Cl2 (0.105 g, 0.00015 mol) was added and degassed with N2 for 5-10 minutes. The reaction mixture was stirred at 95° C. for 2 hours. The reaction mixture was cooled and diluted with ethyl acetate. The organic layer was washed with water, brine, dried over anhydrous sodium sulfate and evaporated under reduced pressure to afford the crude product. The crude product was purified by flash column chromatography (40% ethyl acetate in hexane) to provide the title compound (0.65 g, 62%). 1H NMR (400 MHz, CDCl3): δ 8.00 (d, J=1.6 Hz, 1H), 7.89 (d, J=8.8 Hz, 1H), 7.66 (dd, J′=8.4 Hz, J″=1.6 Hz, 1H), 7.30 (d, J=7.6 Hz, 1H), 7.08 (d, J=8.0 Hz, 1H), 6.99 (t, J=2.0 Hz, 1H), 6.77 (dd, J′=7.6 Hz, J″=1.2 Hz, 1H), 3.90 (s, 8H), 3.84 (br s, 2H), LC-MS (ESI): Calculated mass. 340.11, Observed mass [M+H]+: 341.1 (RT=0.48 min).

Provenance & Evidence