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 3-bromo-5-methyl-5,6,6a,7,8,9,10,12-octahydroindolo[2,3-b]quinolizine for 9-bromo-11-methyl-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole, a yellow solid was obtained in 43% (92 mg). The 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 (75 mg, 71%) as a white powder: mp 270-272° C.; 1H NMR (500 MHz, CD3OD) δ 8.63 (s, 1H), 8.08 (d, J=7.5 Hz, 1H), 7.60 (d, J=7.5 Hz, 1H), 7.58 (d, J=8.5 Hz, 1H), 7.56 (d, J=10.0 Hz, 1H), 7.47 (d, J=1.5 Hz, 1H), 7.06 (dd, J=8.5, 2.0 Hz, 1H), 6.31 (dd, J=7.5, 2.5 Hz, 1H), 6.16 (d, J=2.5 Hz, 1H), 5.26 (s, 2H), 4.75 (d, J=14.5 Hz, 1H), 4.37 (d, J=14.0 Hz, 1H), 3.81-3.78 (m, 1H), 3.74 (s, 3H), 3.72-3.66 (m, 1H), 3.40 (dd, J=17.5, 4.5 Hz, 1H), 3.26-3.23 (m, 1H), 2.99 (dd, J=18.0, 11.0 Hz, 1H), 2.64 (s, 3H), 2.36-2.33 (m, 1H), 2.09-1.98 (m, 2H), 1.85-1.71 (m, 3H); ESI MS m/z 455 [M+H]+; HPLC (Method A)>99.0% (AUC), tR=9.3 min.
