Reaction Steps
A solution of 13 (170 mg, 0.47 mmol) in HCl-saturated dioxane (10 mL) was stirred at 20° C. for 2 h, then evaporated under reduced pressure below 30° C. EDCI-HCl (270 mg, 1.41 mmol), 5,6,7-trimethoxyindole-2-carboxylic acid (118 mg, 0.47 mmol) and DMF (2.5 mL) were then added, and the mixture was stirred at 20° C. for 2 h. Addition of water precipitated a crude product, which was recrystallised twice from CH2Cl2 /iPr2O to give 1-chloromethyl-5-nitro-3-[5,6,7-trimethoxyindol-2-yl)carbonyl]-1,2-dihydro-3H-benz[e]indole (14a) (156 mg, 67%), mp 243-245° C. 1H NMR (CDCl3) δ9.44 (s, 1 H, NH), 9.24 (s, 1 H, H-9), 8.43 (dd, J=7.9, 1.2 Hz, 1 H, H-7), 7.87 (dd, J=7.7, 1.5 Hz, 1 H, H-4), 7.70-7.60 (m, 2 H, H-5,6), 7.03 (d, J=2.5 Hz, 1 H, H-3'), 6.87 (s, 1 H, H-4'), 4.88 (dd, J=10.8, 2.1 Hz, 1 H, H-2), 4.74 (dd, J=10.4, 8.9 Hz, 1 H, H-2), 4.36-4.26 (m, 1 H, H-3), 4.10 (s, 3 H, OCH3), 3.99 (dd, J=11.4, 3.1 Hz, 1 H, CHHCl), 3.95 (s, 3 H, OCH3), 3.92 (s, 3 H, OCH3), 3.58 (dd, J=11.4, 9.9 Hz, 1 H, CHHCl).
