2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 22648049, compound

Participants

Reaction Steps

To a solution of 1-(2,6-dichlorophenyl)-5-(2-chlorofluorophenyl)-7-methoxy-3,4-dihydro-2(1H)-quinazolinone (112 mg, 0.248 mmol) (INTERMEDIATE 30) in 1,4-dioxane (5 mL) at 65° C. under an argon atmosphere was added a solution of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (115 mg, 0.51 mmol) in 1,4-dioxane (2.5 mL). After 2 h the solution was cooled to RT and partitioned between NaHCO3 and EtOAc. The phases were separated and the organic phase washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified by silica gel chromatography using 3 to 5% acetone in DCM as the eluent to give 1-(2,6-dichlorophenyl)-5-(2-chloro-4-fluorophenyl)-7-(methoxy)-2(1H)-quinazolinone. 1H NMR(CDCl3, 500 MHz): δ 3.70 (s, 3H), 5.94 (d, 1H, J=2.1 Hz), 6.74 (d, 1H, J=2.1 Hz), 7.18 (app dt, 1H, J=8.1, 2.5 Hz), 7.35 (m, 1H), 7.42 (m, 1H), 7.47 (t, 1H, J=8.2 Hz), 7.56-7.60 (m, 2H). MS(ES) 449 (M+H); LC 1: 3.40 min.

Provenance & Evidence