Sodium Carbonate → 2-(2-methyl-3-(o-tolyl)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one

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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; 50.3 mg, 0.161 mmol), o-tolylboronic acid (Aldrich; 32.8 mg, 0.241 mmol), Na2CO3 (51.1 mg, 0.482 mmol), and Pd(PPh3)4 (Strem Chemicals, Inc.; 9.29 mg, 8.04 μmol) in a mixture of 1,4-dioxane (1.5 mL) and water (0.500 mL) was stirred under argon at 100° C. for 45 min. The mixture was concentrated onto silica gel and chromatographically purified (silica gel, 50-100% EtOAc/hexanes, then 0-10% MeOH/DCM) to provide 2-(2-methyl-3-(o-tolyl)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (54.6 mg, 0.148 mmol, 92% yield) as a brown solid. 1H NMR (400 MHz, CDCl3) δ ppm 12.12 (1H, br. s.), 8.11 (1H, dd, J=7.4, 0.8 Hz), 7.90 (1H, dd, J=8.3, 0.9 Hz), 7.77 (1H, t, J=8.0 Hz), 7.31-7.49 (4H, m), 7.25 (1H, d, J=2.2 Hz), 5.38 (1H, br. s.), 3.58 (2H, td, J=6.7, 2.1 Hz), 2.85 (2H, t, J=6.8 Hz), 2.59 (3H, s), 2.21 (3H, s). m/z (ESI, +ve) 368.9 (M+H)+.

Provenance & Evidence