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 8-bromo-10-methyl-2,3,5,10,11,11a-hexahydro-1H-indolizino[7,6-b]indole for 9-bromo-11-methyl-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole, a white solid was obtained in 31% (81 mg). The yellow solid was dissolved in CH3OH (1 mL) and was treated with 2 N HCl in Et2O (1 mL). The resulting solid was isolated by filtration and dried under vacuum to give the title compound (60 mg, 64%) as a white powder: mp 260-263° C.; 1H NMR (500 MHz, CD3OD) δ 8.70 (d, J=1.5 Hz, 1H), 8.25 (d, J=7.5 Hz, 1H), 7.70 (d, J=8.0 Hz, 1H), 7.62 (d, J=7.5 Hz, 1H), 7.59 (d, J=8.5 Hz, 1H), 7.48 (d, J=1.5 Hz, 1H), 7.06 (dd, J=8.5, 2.0 Hz, 1H), 6.32 (dd, J=7.5, 3.0 Hz, 1H), 6.16 (d, J=2.5 Hz, 1H), 5.30 (s, 2H), 4.90 (d, J=14.0 Hz, 1H), 4.37 (d, J=14.0 Hz, 1H), 3.84-3.91 (m, 2H), 3.75 (s, 3H), 3.57 (dd, J=17.0, 4.0 Hz, 1H), 3.41-3.39 (m, 1H), 3.06 (dd, J=16.5, 11.5 Hz, 1H), 2.70 (s, 3H), 2.63-2.60 (m, 1H), 2.38-2.23 (m, 2H), 1.99-1.95 (m, 1H); ESI MS m/z 441 [M+H]+; HPLC (Method A) 97.7% (AUC), tR=9.1 min.
