Reaction Steps
A mixture of 222 (75 mg, 0.20 mmol), 5-[2-(dimethylamino)ethoxy]indole-2-carboxylic acid hydrochloride (73 mg, 0.26 mmol), EDCI (152 mg, 0.79 mmol) and TsOH (5 mg, 0.03 mmol) in DMA (1.5 mL) was stirred at room temperature for 1 h, then poured into dilute aqueous NH3. The precipitate was collected, washed with water, and dissolved in CH2Cl2 (250 mL). The solution was dried, filtered, concentrated under reduced pressure to a small volume, and then diluted with i-Pr2O to give tert-butyl 1-(chloromethyl)-3-{5-[2-(dimethylamino)ethoxy]indol-2-carbonyl}-5-nitro-1,2-dihydro-3H-benzo[e]indole-7-carbamate (223) (91 mg, 75%) as a yellow solid: mp (THF/CH2Cl2/hexane)>250° C.; 1H NMR [(CD3)2SO] δ 11.67 (d, J=1.6 Hz, 1H), 9.85 (s, 1H), 9.12 (s, 1H), 8.69 (d, J=1.9 Hz, 1H), 8.14 (d, J=9.2 Hz, 1H), 7.79 (dd, J=9.2, 2.0 Hz, 1H), 7.41 (d, J=−8.9 Hz, 1H), 7.18 (d, J=2.3 Hz, 1H), 7.15 (d, J=1.7 Hz, 1H), 6.93 (dd, J=8.9, 2.4 Hz, 1H), 4.90 (t, J=10.2 Hz, 1H), 4.67 (dd, J=10.9, 2.4 Hz, 1H), 4.58-4.51 (m, 1H), 4.16-4.03 (m, 4H), 2.66 (t, J=5.8 Hz, 2H), 2.24 (s, 6H), 1.53 (s, 9H). Anal. (C31H34ClN5O6) C, H, N.
