Sodium Carbonate → HCID 22648169, compound

Participants

Reaction Steps

Palladium tetrakis triphenylphosine (140 mg, 0.12 mmol) was added to 1-(2,6-dichlorophenyl)-5-bromo-7-methoxy-3,4-dihydro-2(1H)-quinazolinone (1.02 g, 2.54 mmol) (INTERMEDIATE 23), 2-chlorophenyl boronic acid (642 mg, 4.11 mmol) and sodium carbonate (436 mg, 4.11 mmol) in 150 mL toluene, 40 mL EtOH and 40 mL water under an argon atmosphere. After refluxing 3 h the solution was cooled to RT and partition between water and EtOAc. The organic phase was washed with water′(1×) and brine (1×) and dried over MgSO4. The solution was filtered and concentrated. The residue was absorbed on SiO2 and purified by silica gel bromatography using 3 to 5% acetone in DCM to give 1-(2,6-dichlorophenyl)-5-(2-chlorophenyl)-7-methoxy-3,4-dihydro-2(1H)-quinazolinone as a white solid. 1H NMR(CDCl3, 500 MHz): δ 3.68 (s, 3H), 4.17 (d, 1H, J=14.0 Hz), 4.36 (d, 1H, J=14.0 Hz), 5.28 (s, 1H), 5.74 (d, 1H, J=2.3 Hz), 6.43 (d, 1H, J=2.5 Hz), 7.29-7.37 (m, 4H), 7.47-7.51 (m, 3H). MS(ES) 433 (M+H); LC 1: 3.12 min.

Provenance & Evidence