Reaction Steps
A mixture of aniline (27.4 mg, 0.303 mmol), methyl 1-benzenesulfonyl-7-chloro-3-carboxymethyl-1,3,4,5-tetrahydrobenz[cd]indole-2-carboxylate (120 mg, 0.275 mmol), 1-hydroxy-benzotriazole (46 mg, 0.303 mmol), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (47 mg, 0.303 mmol) in DMF (2.5 mL) was stirred for 20 h at room temperature, acidified to pH 1 by adding 1N HCl, and extracted with 1:1 toluene/ethyl acetate. The organic layer was washed successively with 1N HCl, water, saturated sodium bicarbonate, water, and brine, dried over magnesium sulfate, and concentrated to give 161 mg of the title compound (quant): 1H NMR (CDCl3) δ7.95 (d, 2H, J=7.3 Hz), 7.90 (s, 1H), 7.85 (s, 1H), 7.58 (t, 1H, J=7.3 Hz), 7.52 (d, 1H, J=8.3 Hz), 7.46 (t, 1H, J=8.3 Hz), 7.30 (t, 1H, J=8.3 Hz), 7.15 (t, 1H, J=7.05 (s, 1H), 3.84 (s, 3H), 3.71 (m, 1H), 2.92 (ddd, 1H, J=17.2, 12.2, 3.6 Hz), 2.80 (md, 1H, J=17.2 Hz), 2.65 (dd, 1H, J=14.2, 4.0 Hz), 2.47 (dd, 1H, J=14.2, 9.6 Hz), 2.19 (md, 1H, J=13.6 Hz), 1.89 (m, 1H).
