Reaction Steps
A vial was charged with the title compound from Example 12 Step C (375 mg, 0.669 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydropyridine-1(2H)-carboxylate (310 mg, 1.00 mmol; Tetrahedron Lett, 2000, 41, 3705-3708) and trans-dichlorobis(triphenylphosphine)palladium (II) (47 mg, 0.067 mmol). Acetonitrile (2.2 mL) and sodium carbonate (1.7 mL, 1.0 M aqueous, 1.7 mmol) were added, and the resulting mixture was degassed via nitrogen sparge. The reaction mixture was stirred at 70° C. for 15 h, then was allowed to cool to ambient temperature and was loaded directly onto a silica gel column. Purification by chromatography on silica gel (0 to 50% EtOAc in hexanes, then 50 to 100% EtOAc in hexanes) provided the title compound: LCMS m/z 663.0 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 8.15 (d, J=8.0 Hz, 1H), 8.12 (s, 1H), 7.86 (t, J=8.0 Hz, 1H), 7.79 (d, J=2.0 Hz, 1H), 7.51 (d, J=8.0 Hz, 1H), 7.36 (d, J=8.5 Hz, 2H), 7.32 (d, J=8.5 Hz, 2H), 7.16 (dd, J=8.5, 2.0 Hz, 1H), 6.95 (d, J=8.0 Hz, 1H), 6.08-6.02 (m, 1H), 5.11 (s, 2H), 4.39 (q, J=7.0 Hz, 2H), 4.08-4.06 (m, 2H), 3.65-3.63 (m, 2H), 2.54-2.50 (m, 2H), 2.35 (s, 3H), 1.49 (s, 9H), 1.41 (q, J=7.0 Hz, 3H).
