Sodium Carbonate → HCID 89785208, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-(3-chloro-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 425; 38.4 mg, 0.123 mmol), (2-chlorophenyl)boronic acid (Aldrich; 28.8 mg, 0.184 mmol), Na2CO3 (39.0 mg, 0.368 mmol), and Pd(PPh3)4 (Strem Chemicals, Inc.; 7.09 mg, 6.14 μmol) in a mixture of 1,4-dioxane (1.5 mL) and water (0.500 mL) was stirred under argon at 100° C. for 20 min. The reaction mixture was then concentrated onto silica gel and chromatographically purified (silica gel, 50-100% EtOAc/hexanes, then 0-10% MeOH/DCM) to provide 2-(3-(2-chlorophenyl)-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (40.3 mg, 0.104 mmol, 84% yield) as a brown solid. 1H NMR (400 MHz, CDCl3) δ ppm 12.00 (1H, br. s.), 8.11 (1H, dd, J=7.6, 1.2 Hz), 7.92 (1H, dd, J=8.4, 1.2 Hz), 7.79 (1H, t, J=8.0 Hz), 7.59-7.64 (1H, m), 7.46-7.55 (3H, m), 7.24 (1H, d, J=2.2 Hz), 5.65 (1H, br. s.), 3.61 (2H, t, J=6.7 Hz), 2.89 (2H, td, J=6.7, 1.4 Hz), 2.67 (3H, s). m/z (ESI, +ve) 388.9 (M+H)+.

Provenance & Evidence