Sodium Carbonate → HCID 89793854, 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; 37.7 mg, 0.121 mmol), furan-3-ylboronic acid (Boron Molecular, Research Triangle, N.C.; 20.23 mg, 0.181 mmol), Na2CO3 (38.3 mg, 0.362 mmol), and Pd(PPh3)4 (Strem Chemicals, Inc.; 6.96 mg, 6.03 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-(furan-3-yl)-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (37.0 mg, 0.107 mmol, 89% yield) as a yellow-orange solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.81 (1H, br. s.), 8.52 (1H, s), 8.02 (1H, dd, J=7.2, 1.4 Hz), 7.95 (1H, t, J=1.7 Hz), 7.83 (1H, dd, J=8.2, 1.4 Hz), 7.74-7.80 (1H, m), 7.25 (1H, s), 7.24 (1H, dd, J=1.8, 0.8 Hz), 7.00 (1H, br. s.), 3.45 (2H, td, J=6.7, 2.3 Hz), 2.90-2.94 (2H, m), 2.90 (3H, s). m/z (ESI, +ve) 344.9 (M+H)+.

Provenance & Evidence