Benzoyl chloride → HCID 49853689, compound

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (30 mg, 0.75 mmol) was added to dry DMF (5 ml) in a nitrogen atmosphere. The reaction flask was cooled in an ice-bath to 0° C., and 2-(4-(8-bromo-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)phenyl)-2-methylpropanenitrile (Intermediate 1, 100 mg, 0.25 mmol) was added. After 15 minutes benzoyl chloride (42 mg, 0.29 mmol) was added, and the reaction mixture was heated at 50° C. for 24 hours. The reaction mixture was concentrated in vacuum. The crude product was purified by column chromatography (silica gel, 2% acetone in chloroform) to obtain the title compound. Yield: 13 mg (10%); 1H NMR (DMSO-d6, 300 MHz): δ 9.410 (s, 1H), 7.998-8.028 (d, 1H, J=9 Hz), 7.939-7.963 (d, 2H, J=7.2 Hz), 7.848-7.876 (d, 2H, J=8.4 Hz), 7.764-7.792 (d, 3H, J=8.4 Hz), 7.644-7.669 (m, 1H), 7.48-7.56 (m, 2H), 6.865-6.872 (d, 1H, J=2.1 Hz), 1.78 (s, 6H); MS: m/z 511 (M+1).

Provenance & Evidence