Reaction Steps
To a solution of 2-[4-benzyloxy-2-(5,6,7-trimethoxyindole-2-carboxamido)naphthalen-1-yl]ethyl acetate (0.10 g, 0.18 mmol) in MeOH (2 mL) was added potassium carbonate (29.15 mg, 0.21 mmol) at room temperature and stirred overnight. The reaction mixture was diluted with AcOEt (50 mL) and washed with H2O (10 mL), saturated aqueous NaCl (20 mL), and then the organic layer was dried (Na2SO4) and concentrated under reduced pressure to yield as a yellow oil 2-[4-benzyloxy-2-(5,6,7-trimethoxyindole-2-carboxamido)naphthalen-1-yl]ethanol (82 mg, 87%); 1H NMR (CDCl3, 500 MHz) δ 9.96 (s, 1H), 9.25 (s, 1H), 8.39 (d, 8.0, 1H), 7.85 (d, 8.5, 1H), 7.75 (s, 1H), 7.71 (dd, 3.5, 5.8, 1H), 7.57 (d, 7.5, 2H), 7.53 (m, 1H), 7.43 (t, 7.5, 2H), 7.36 (t, 7.0, 1H), 7.06 (s, 1H), 6.84 (s, 1H), 5.30 (s, 2H), 4.21 (t, 6.0, 2H), 4.08 (s, 3H), 3.95 (s, 3H), 3.91 (s, 3H), 3.37 (t, 5.0, 2H); EIMS m/z 527 (M+H+); IR (neat) νmax 3272, 2932, 1726, 1644, 1594, 1540, 1505, 1464, 1409, 1370, 1263, 1236, 1127, 1103, 1049, 997, 831, 760, 701 cm−1.
