Reaction Steps
According to the procedure of Example 2 (step b), except substituting 4-((6-methylpyridin-3-yl)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 25% (60 mg). The white 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 (57 mg, 81%) as a white powder: mp 305° C. (decompose); 1H NMR (500 MHz, CD3OD) δ 9.14 (d, J=2.0 Hz, 1H), 8.82 (dd, J=8.5, 2.0 Hz, 1H), 8.03 (d, J=8.5 Hz, 1H), 7.90 (d, J=7.0 Hz, 1H), 7.64 (d, J=8.5 Hz, 1H), 7.58 (d, J=1.5 Hz, 1H), 7.15 (dd, J=8.5, 2.0 Hz, 1H), 7.07 (d, J=2.0 Hz, 1H), 6.91 (dd, J=7.5, 2.0 Hz, 1H), 4.92 (d, J=14.0 Hz, 1H), 4.39 (d, J=14.0 Hz, 1H), 3.90-3.88 (m, 2H), 3.77 (s, 3H), 3.59 (dd, J=17.0, 4.0 Hz, 1H), 3.41-3.38 (m, 1H), 3.08 (dd, J=16.5, 11.5 Hz, 1H), 2.86 (s, 3H), 2.64-2.61 (m, 1H), 2.39-2.24 (m, 2H), 2.01-1.97 (m, 1H); ESI MS m/z 411 [M+H]+; HPLC (Method A)>99% (AUC), tR=8.9 min.
