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 9-bromo-7-methyl-2,3,5,6,7,11c-hexahydro-1H-indolizino[7,8-b]indole for 9-bromo-11-methyl-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole, a yellow solid was obtained in 25% (72 mg). The yellow solid was dissolved in CH3OH (1 mL) and 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 (68 mg, 81%) as a yellow-brown powder: mp 280-282° C.; 1H NMR (500 MHz, CD3OD) δ 8.55 (d, J=2.0 Hz, 1H), 7.91 (dd, J=8.0, 2.0 Hz, 1H), 7.61 (d, J=8.5 Hz, 1H), 7.59 (d, J=7.5 Hz, 1H), 7.48 (d, J=2.0 Hz, 1H), 7.42 (d, J=8.0 Hz, 1H), 7.06 (dd, J=8.5, 2.0 Hz, 1H), 6.29 (dd, J=7.5, 2.5 Hz, 1H), 6.15 (d, J=2.5 Hz, 1H), 5.22 (s, 2H), 5.11 (br s, 1H), 3.74 (s, 3H), 3.74-3.72 (m, 4H), 3.47-3.44 (m, 1H), 3.24-3.22 (m, 1H), 2.73-2.71 (m, 1H), 2.59 (s, 3H), 2.25-2.17 (m, 3H); ESI MS m/z 441 [M+H]+; HPLC (Method A)>99% (AUC), tR=9.2 min.
