4-Methoxybenzenesulfonyl chloride → HCID 46842450, compound

Participants

Reaction Conditions

Reaction Steps

3-(4-chlorophenyl)-2-(1H-pyrrolo[2,3-b]pyridin-5-yl)quinazolin-4(3H)-one (0.156 g, 0.42 mmol) and benzyltriethylammonium chloride (0.003 g, 0.013 mmol) were combined in CH2Cl2 (10 mL). NaOH powder (0.052 g, 1.31 mmol) was added and the mixture was cool to 0° C. 4-methoxy-benzenesulfonyl chloride (0.107 g, 0.52 mmol) was added, and the reaction mixture was stirred for 30 minutes at 0° C., and warmed to room temperature. After 18 hours, additional NaOH powder (0.050 gm 1.30 mmol), benzyltriethylammonium chloride (0.010 g, 0.04 mmol), and 4-methoxy-benzenesulfonyl chloride (0.200 g, 0.97 mmol) were added and the reaction was continued at room temperature for an additional 6 hours. After concentration and purification by silica gel chromatography, eluting with 100% CH2Cl2 to 100% ethyl acetate to 50% methanol/ethyl acetate, the title compound was afforded as a white solid (0.137 g, 60%). 1H-NMR (300 MHz, DMSO-6): δ8.37 (d, 1.7 Hz, 1H), 8.22 (d, J=8.0 Hz, 1H), 8.07 (d, J=1.7 Hz, 1H), 7.98 (d, J=8.9 Hz, 2H), 7.88-7.93 (m, 2H), 7.76 (d, J=8.0 Hz, 1H), 7.61-7.66 (m, 1H), 7.34-7.45 (m, 4H), 7.11 (d, J=9.0 Hz, 2H), 6.79 (d, J=3.9 Hz, 1H), 3.82 (s, 3H). MS (APCI) m/z: 543 (M+H)+.

Provenance & Evidence