Reaction Steps
A suspension of 14 (0.10 g, 0.24 mmol) in dioxane (15 mL) was saturated with HCl, stirred at r.t. for 5 h and evaporated. 5-Methoxy-1-H-indole-2-carboxylic acid (0.054 g, 0.28 mmol), EDCI (0.23 g, 1.17 mmol) and DMA (5 mL) were added to the remaining yellow solid, and the red mixture was stirred at r.t. for 52 h. The mixture was partitioned between CH2Cl2 and cold 5% KHCO3 solution. The aqueous layer was extracted with CH2Cl2 (×3). The CH2Cl2 extracts were dried (brine, Na2SO4). Flash chromatography (EtOAc/petroleum ether, 7:3) gave 5-(benzyloxy)-1-(chloromethyl)-3-[(5-methoxy-1H-indol-2-yl)carbonyl]-2,3-dihydro-1H-pyrrolo[3,2-f]quinoline (17d) (0.11 g, 98%) as a yellow solid: mp 186–189° C.; 1H NMR (CDCl3) δ 9.55 (s, 1 H), 8.88 (dd, J=4.2, 1.7, 1 H), 8.37 (s, 1 H), 7.99 (dd, J=8.3, 1.6, 1 H), 7.56 (d, J=7.3, 2 H), 7.42 (dd, J=8.3, 4.1, 1 H), 7.33 (m, 4 H), 7.10 (d, J=2.3, 1 H), 6.99 (m, 2 H), 5.48 (d, J=12.5, 1 H), 5.42 (d, J=12.6, 1 H), 4.74 (dd, J=10.9, 2.0, 1 H), 4.61 (dd, J=10.6, 8.7, 1 H), 4.05 (m, 1 H), 3.85 (s, 3 H), 3.84 (dd, J=11.2, 4.1, 1 H), 3.45 (dd, J=11.0, 10.5, 1 H); 13C NMR (CDCl3) δ 160.7, 155.4, 154.7, 147.9, 142.4, 138.4, 136.4, 131.4, 130.5, 130.2, 128.6, 128.2, 128.0, 127.7, 125.2, 122.4, 117.0, 115.4, 112.7, 106.2, 102.5, 102.4, 70.9, 55.7, 55.2, 45.9, 42.6.
