Reaction Steps
In sealed pressure tube and stir bar was charged Pd(OAc)2 (5 mg, 0.08 equiv.), 2-dicyclohexylphosphino-2′,6′-dimethoxyphenyl 1 (18 mg, 0.16 equiv.), a-carbolines (83 mg, 0.267 mmol), trans vinyl phenyl boronic acid (119 mg, 3.0 equiv.) and K3PO4 (142 mg, 2.5 equiv.). The tube was evacuated and back-filled with argon (this was repeated three additional times). 700 μl of anhydrous 1,4-dioxane was added (when degassed solvent was used) and the reaction mixture was allowed to stir at 100° C. overnight. After cooling to room temperature, the products were extracted from the water layer with ethyl acetate, dried over MgSO4, filtered through celite and solvents were removed under reduced pressure. The crude product was purified by flash chromatography (CH2Cl2/EtOAc 9:1) to afford R315 in 65% yield as a white solid; mp>220° C. (MeOH); IR: 3060, 2994, 2833, 1606, 1517, 1485, 1460, 1232, 957, 813, 740, 692 cm−1; 1H-NMR (300 MHz, DMSO-d6): δ 11.86 (bs, 1H), 8.95 (d, 1H, J=2.1 Hz), 8.61 (d, 1H, J=2.1 Hz), 8.47 (d, 1H, J=1.3 Hz), 7.74 (dd, 1H, J=1.9, 8.5 Hz), 7.71 (d, 214, J=8.9 Hz), 7.63 (d, 2H, J=7.1 Hz), 7.54 (d, 1H, J=8.5 Hz), 7.46 (d, 1H, J=16.4 Hz), 7.43-7.39 (m, 2H), 7.37 (d, 1H, J=16.4 Hz), 7.27 (t, 1H, J=7.4 Hz), 7.07 (d, 2H, J=8.9 Hz), 3.82 (s, 3H); 13C-NMR (75 MHz, DMSO-d6): δ 158.4 (C), 152.0 (C), 146.5 (CH), 138.5 (C), 137.4 (C), 133.4 (C), 131.9 (C), 128.8 (2 CH), 127.7 (2 CH), 127.4 (CH), 126.8 (CH), 126.3 (CH), 126.2 (2 CH), 125.6 (CH), 124.9 (CH), 127.8 (C), 121.1 (C), 118.9 (CH), 115.8 (C), 114.4 (2 CH), 111.7 (CH), 55.2 (CH3); MS (ESI) m/z 377.3 [M+H+]; HRMS (ESI): Calcd for C26H20N2O: 377.1654. Found: 377.1653.
