Reaction Steps
According to the procedure of Example 2 (step b), except substituting 4-(5-chloropyridin-2-yl)pyridin-2(1H)-one for 4-(benzyloxypyridin-2(1H)-one and substituting 10-Bromo-12-methyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine for 9-bromo-11-methyl-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole, a yellow oil was obtained in 30% (56 mg). The yellow oil 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 (51 mg, 84%) as a yellow solid: mp 210-213° C.; 1H NMR (500 MHz, CD3OD) δ 8.73 (d, J=2.5 Hz, 1H), 8.04 (d, J=8.5 Hz, 1H), 8.00 (dd, J=8.5, 2.0 Hz, 1H), 7.79 (d, J=7.0 Hz, 1H), 7.68 (d, J=8.5 Hz, 1H), 7.57 (d, J=1.5 Hz, 1H), 7.31 (d, J=1.5 Hz, 1H), 7.20 (dd, J=7.5, 2.0 Hz, 1H), 7.16 (dd, J=8.5, 2.0 Hz, 1H), 4.93 (dd, J=12, 4.0 Hz, 1H), 4.17-4.11 (m, 1H), 3.76 (s, 3H), 3.67-3.60 (m, 3H), 3.24-3.21 (m, 2H), 2.35-2.33 (m, 1H), 2.12-1.99 (m, 3H), 1.94-1.88 (m, 2H); ESI MS m/z 445 [M+H]+; HPLC (Method A) 97.3% (AUC), tR=12.9 min.
