Cesium fluoride → HCID 89785053, 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; 38.0 mg, 0.122 mmol), 2-(tributylstannyl)pyridine (Aldrich; 0.043 mL, 0.134 mmol), CuI (2.314 mg, 0.012 mmol), cesium fluoride (36.9 mg, 0.243 mmol), and Pd(PPh3)4 (Strem Chemicals, Inc.; 7.02 mg, 6.08 μmol) in a mixture of 1,4-dioxane (2.0 mL) and DMF (2.0 mL) was stirred in a sealed tube under argon at 140° C. for 1 h. 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-(pyridin-2-yl)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (31.2 mg, 0.088 mmol, 72% yield) as a brown solid. 1H NMR (400 MHz, CDCl3) δ ppm 12.20 (1H, br. s.), 8.85 (1H, d, J=4.5 Hz), 8.09 (1H, dd, J=7.4, 1.0 Hz), 7.94-8.01 (1H, m), 7.90 (2H, d, J=8.2 Hz), 7.74-7.81 (1H, m), 7.50 (1H, ddd, J=7.3, 4.9, 1.1 Hz), 7.25 (1H, br. s.), 5.32 (1H, br. s.), 3.63 (2H, td, J=6.8, 2.1 Hz), 2.97 (3H, s), 2.94 (2H, t, J=6.8 Hz). m/z (ESI, +ve) 356.0 (M+H)+.

Provenance & Evidence