Reaction Steps
A solution of 14o (162 mg, 0.29 mmol) in THF (15 mL) was hydrogenated over PtO2 at 55 psi for 2 h. After removal of the catalyst, the solution was concentrated to a small volume under reduced pressure below 25° C. and diluted with iPr2O to give a crude product. This was purified by precipitation from an EtOAc solution with petroleum ether at 20° C. to give 5-amino-1-[(methanesulfonyloxy)methyl]-3-[(5,6,7-trimethoxyindol-2-yl)carbonyl]-1,2-dihydro-3H-benz[e]indole (15o) (116 mg, 76%) as an unstable solid, mp >260° C. 1H NMR [(CD3)2SO] δ 11.41 (d, J=1.6 Hz, 1 H, NH), 8.08 (d, J=8.5 Hz, 1 H, H-6), 7.76 (d, J=8.3 Hz, 1 H, H-9), 7.67 (s, 1 H, H-4), 7.49 (t, J=7.6 Hz, 1 H, H-8), 7.30 (t, J=7.6 Hz, 1 H, H-7), 7.04 (d, J=2.0 Hz, 1 H, H-3'), 6.96 (s, 1 H, H-4'), 6.15 (v br s, 2 H, NH2), 4.66 (dd, J=10.9, 8.5 Hz, 1 H, H-2), 4.47 (dd, J=9.9, 3.4 Hz, 1 H, H-2), 4.41 (d, J=10.9 Hz, 1 , CHHO), 4.17 (t, J=9.2 Hz, 1 H, CHHO), 4.13-4.04 (m, 1 H, H-1), 3.94 (s, 3 H, OCH3), 3.82 (s, 3 H, OCH3), 3.80 (s, 3 H, OCH3), 3.07 (s, 3 H, SO2CH3). Anal. Calculated for C26H27N3O7S: C, 59.4; H, 5.2; N, 8.0. Found: C, 59.3; H, 5.4; N, 8.1%.
