Dimethylformamide → 4-(2-Chloro-7-(3-(methylsulfonyl)phenyl)quinazolin-4-yl)morpholine

Participants

Reaction Conditions

Reaction Steps

To a 50 mL round bottom flask, 4-(7-bromo-2-chloroquinazolin-4-yl)morpholine (0.25 g, 0.0007 mol—Preparation 1), 3-methylsulfonylphenylboronic acid (0.137 g, 0.0006 mol), sodium carbonate (0.121 g, 0.00105 mol), DMF (8 mL) and water (2 mL) were added. The reaction vessel was degassed with N2 for 5-10 minutes. To the same reaction mixture, Pd(PPh3)2Cl2 (0.027 g, 0.000035 mol) was added and the mixture again degassed with N2 for 5-10 minutes. The reaction mixture was stirred at 95° C. for 2 hours. The reaction mixture was cooled and water was added. The crude product was extracted with ethyl acetate. The organic layer was washed with water, brine and dried over sodium sulfate. The solvent was removed under the reduced pressure to afford the crude product. The crude product was purified by column chromatography (60-120 silica gel, 50-100% ethyl acetate in n-hexane) to provide the desired product (0.2 g, 65%). 1H NMR (300 MHz, CDCl3): δ 8.25 (br s, 1H), 8.06-7.94 (m, 3H), 7.75-7.46 (m, 3H), 3.93 (br s, 4H), 3.91 (br s, 4H), 3.12 (s, 3H): LC-MS (ESI): Calculated mass: 403.0; Observed mass [M+H]+: 404.0 (RT=1.30 min).

Provenance & Evidence