Reaction Steps
A solution of 8-bromo-N-(tert-butyl)-3-phenylquinoxalin-2-amine (83.0 mg, 0.233 mmol), 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 609; 172 mg, 0.466 mmol), K3PO4 (148 mg, 0.699 mmol), dicyclohexyl(2′,4′,6′-triisopropyl-[1,1′-biphenyl]-2-yl)phosphine (XPhos; Strem Chemicals, Inc.; 11.11 mg, 0.023 mmol), and Pd2dba3 (Aldrich; 10.67 mg, 0.012 mmol) in a mixture of 1,4-dioxane (2.0 mL) and water (0.400 mL) was stirred under argon at 100° 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-(3-(tert-butylamino)-2-phenylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (50.0 mg, 0.122 mmol, 52% yield) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ ppm 12.72 (1H, br. s.), 7.99 (1H, dd, J=7.6, 1.4 Hz), 7.77 (1H, dd, J=8.1, 1.3 Hz), 7.71 (2H, dd, J=7.8, 1.6 Hz), 7.53-7.62 (3H, m), 7.41 (1H, t, J=7.8 Hz), 7.13 (1H, d, J=2.2 Hz), 5.98-6.21 (1H, m), 5.36 (1H, s), 3.71 (2H, t, J=6.9 Hz), 3.03 (2H, t, J=7.0 Hz), 1.59 (9H, s). m/z (ESI, +ve) 412.0 (M+H)+.
