Reaction Steps
A solution of 14c (170 mg, 0.37 mmol) in THF (60 mL) was hydrogenated over PtO2 at 50 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 EtOAc/iPr2O to give 15c (141 mg, 89%). mp >300° C. 1H NMR [(CD3)2SO] δ 11.61 (d, J=1.4 Hz, 1 H, indole NH), 9.84 (s, 1 H, NHCO), 8.08 (d, J=8.5 Hz, 1 H, H-6), 8.05 (d, J=1.4 Hz, 1 H, H-4'), 7.76 (d, J=8.2 Hz, 1 H, H-9), 7.71 (s, 1 H, H-4), 7.46 (t, J=7.5 Hz, 1 H, H-8), 7.42 (d, J=8.9 Hz, 1 H, H-7'), 7.33 (dd, J=8.8, 1.9 Hz, 1 H, H-6'), 7.29 (t, J=7.5 Hz, 1 H, H-7), 7.14 (d, J=1.7 Hz, 1 H, H-3'), 5.98 (s, 2 H, NH2), 4.74 (dd, J=10.8, 9.0 Hz, 1 H, H-2), 4.51 (dd, J=11.0, 1.6 Hz, 1 H, H-2), 4.17-4.08 (m, 1 H, H-1), 3.97 (dd, J=11.0, 3.0 Hz, 1 H, CHHCl), 3.77 (dd, J=10.9, 7.8 Hz, 1 H, CHHCl), 2.06 (s, 3 H, CH3).
