Cesium fluoride → 2-(2-methyl-3-(3-methylpyridin-2-yl)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one

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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; 33.7 mg, 0.108 mmol), 3-methyl-2-(tributylstannyl)pyridine (Indofine Chemical Company, Inc., Hillsborough, N.J.; 0.040 mL, 0.119 mmol), CuI (2.052 mg, 10.78 μmol), cesium fluoride (32.7 mg, 0.216 mmol), and Pd(PPh3)4 (Strem Chemicals, Inc.; 6.23 mg, 5.39 μmol) in DMF (2.0 mL) was stirred under argon in a microwave process vial at 140° C. for 30 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-(3-methylpyridin-2-yl)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (16.8 mg, 0.045 mmol, 42% yield) as a yellow-orange solid. 1H NMR (400 MHz, CDCl3) δ ppm 11.91 (1H, br. s.), 8.65 (1H, dd, J=4.5, 0.8 Hz), 8.10 (1H, dd, J=7.4, 1.2 Hz), 7.91 (1H, dd, J=8.2, 1.2 Hz), 7.74-7.82 (2H, m), 7.42 (1H, dd, J=7.8, 4.9 Hz), 7.23 (1H, d, J=2.2 Hz), 5.35 (1H, br. s.), 3.59 (2H, td, J=6.8, 1.9 Hz), 2.86 (2H, t, J=7.0 Hz), 2.64 (3H, s), 2.29 (3H, s). m/z (ESI, +ve) 370.0 (M+H)+.

Provenance & Evidence