Sodium Carbonate → HCID 89793899, 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; 36.7 mg, 0.117 mmol), (2-fluorophenyl)boronic acid (CombiBlocks, Inc., San Diego, Calif.; 24.63 mg, 0.176 mmol), Na2CO3 (37.3 mg, 0.352 mmol), and Pd(PPh3)4 (Strem Chemicals, Inc.; 6.78 mg, 5.87 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-fluorophenyl)-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (39.8 mg, 0.107 mmol, 91% yield) as a brown solid. 1H NMR (400 MHz, CDCl3) δ ppm 12.07 (1H, br. s.), 8.10 (1H, dd, J=7.4, 1.2 Hz), 7.90 (1H, dd, J=8.2, 1.2 Hz), 7.78 (1H, t, J=8.0 Hz), 7.50-7.62 (2H, m), 7.38 (1H, td, J=7.5, 1.0 Hz), 7.27-7.34 (1H, m), 7.25 (1H, br. s.), 5.39 (1H, br. s.), 3.61 (2H, td, J=6.8, 2.0 Hz), 2.89 (2H, t, J=6.9 Hz), 2.75 (3H, d, J=1.6 Hz). 19F NMR (377 MHz, CDCl3) δ ppm −114.59 (1F, br. s.). m/z (ESI, +ve) 373.0 (M+H)+.

Provenance & Evidence