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

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; 36.5 mg, 0.117 mmol), 4,4,5,5-tetramethyl-2-(2-methylfuran-3-yl)-1,3,2-dioxaborolane (Maybridge, Tintagel, UK; 0.040 mL, 0.175 mmol), Na2CO3 (37.1 mg, 0.350 mmol), and Pd(PPh3)4 (Strem Chemicals, Inc.; 6.74 mg, 5.84 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-(2-methyl-3-(2-methylfuran-3-yl)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (35.1 mg, 0.098 mmol, 84% yield) as a yellow-orange solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 11.79 (1H, br. s.), 8.03 (1H, dd, J=7.3, 1.5 Hz), 7.83 (1H, dd, J=8.2, 1.2 Hz), 7.78 (1H, d, J=7.4 Hz), 7.74 (1H, d, J=2.0 Hz), 7.30 (1H, d, J=2.2 Hz), 7.00 (2H, d, J=1.8 Hz), 3.41 (2H, td, J=6.8, 2.4 Hz), 2.88 (2H, t, J=6.8 Hz), 2.75 (3H, s), 2.48 (3H, s). m/z (ESI, +ve) 359.0 (M+H)+.

Provenance & Evidence