Reaction Steps
According to the procedure of Example 2 (step b), except substituting 4-((6-methylpyridin-3-yl)methoxy)pyridin-2(1H)-one for 4-(benzyloxypyridin-2(1H)-one and substituting 10-bromo-8-methyl-1,2,3,4,6,7,8,12c-octahydroindolo[3,2-a]quinolizine for 9-bromo-11-methyl-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole, a pale yellow solid was obtained in 37% (40 mg). The pale yellow solid was dissolved in CH3OH (1 mL) and treated with 2 N HCl in Et2O (1 mL). The solvent was removed under reduced pressure, and the resulting solid was dried under vacuum to give the title compound (45 mg, 97%) as a pale yellow powder: mp 210-214° C.; 1H NMR (500 MHz, CD3OD) δ 8.87 (d, J=1.5 Hz, 1H), 8.62 (dd, J=8.5, 2.0 Hz, 1H), 8.01 (d, J=8.5 Hz, 1H), 7.73 (d, J=8.5 Hz, 1H), 7.64 (d, J=8.0 Hz, 1H), 7.49 (d, J=2.0 Hz, 1H), 7.05 (dd, J=8.5, 2.0 Hz, 1H), 6.35 (dd, J=7.5, 2.5 Hz, 1H), 6.18 (d, J=2.5 Hz, 1H), 5.39 (s, 2H), 4.67 (d, J=11.5 Hz, 1H), 3.81 (dd, J=12.5, 6.0 Hz, 1H), 3.73 (s, 3H), 3.65-3.62 (m, 2H), 3.40-3.37 (m, 2H), 3.22 (dd, J=17.5, 5.5 Hz, 1H), 3.11 (d, J=14.5 Hz, 1H), 2.83 (s, 3H), 2.10-1.79 (m, 5H); ESI MS m/z 455 [M+H]+; HPLC (Method A) 97.2% (AUC), tR=9.4 min.
