HCID 22648049, compound → HCID 22647964, compound

Participants

Reaction Conditions

Reaction Steps

A solution of methylmagnesium bromide (3.0M ethyl ether, 0.5 mL) was added dropwise to 1-(2,6-dichlorophenyl)-5-(2-chloro-4-fluorophenyl)-7-(methoxy)-2(1H)-quinazolinone (230 mg, 0.511 mmol) (INTERMEDIATE 56) in THF (10 mL) at −78C. After 20 min the solution was warmed to 0° C. After 40 min at 0° C. the solution was partitioned between NaHCO3 and EtOAc. The phases were separated and the organic phase washed with brine, dried over MgSO4, filtered and concentrated. The crude was absorbed on SiO2 and purified by silica gel chromatography using 2% acetone in DCM as the eluent to give 1-(2,6-dichlorophenyl)-3-methyl-5-(2-chloro-4-fluorophenyl)-7-methoxy-3,4-dihydro-2(1H)-quinazolinone. 1H NMR(CDCl3, 500 MHz): diastereomeric atropisomers δ 1.29 (m, 3H), 3.69 (s, 3H), 4.31 (m, 0.5H), 4.41 (m, 0.5H), 5.32 (m, 0.5H), 5.35 (m, 0.5H), 5.76 (m, 1H), 6.37 (d, 0.5H, J=2.5 Hz), 6.44 (d, 0.5H, J=2.2 Hz), 7.08-7.14 (m, 1H), 7.28-7.40 (m, 3H), 7.50-7.56 (m, 2H). MS(ES) 465 (M+H); LC 1: 3.63 min. and MS(ES) 465 (M+H); LC 1: 3.71 min.

Provenance & Evidence