Reaction Steps
To a solution of 2-[4-benzyloxy-2-(5,6,7-trimethoxyindole-2-carboxamido)naphthalen-1-yl]ethanol (80 mg, 0.15 mmol) and triethylamine (0.09 mL, 0.61 mmol) in CH2Cl2 (2 mL) was added methanesulfonyl chloride (0.05 mL, 0.61 mmol) with ice bath, and then the mixture was stirred for 1 h. The reaction mixture was diluted with CH2Cl2 (50 mL) and washed with H2O (10 mL) and saturated aqueous NaCl (20 mL), and then the organic layer was dried (Na2SO4) and concentrated under reduced pressure to yield as a brown oil 2-[4-benzyloxy-2-(5,6,7-trimethoxyindole-2-carboxamido)naphthalen-1-yl]ethyl methanesulfonate (0.11 g, quant); 1H NMR (CDC3, 500 MHz) δ 9.24 (s, 1H), 8.47 (s, 1H), 8.41 (d, 8.0, 1H), 7.85 (d, 8.5, 1H), 7.71 (dd, 3.5, 5.5, 1H), 7.60 (t, 7.0, 1H), 7.48-7.56 (m, 3H), 7.44 (t, 8.0, 2H), 7.37 (t, 7.5, 1H), 7.18 (s, 1H), 6.88 (s, 1H), 5.28 (s, 2H), 4.63 (t, 6.5, 2H), 4.09 (s, 3H), 3.95 (s, 3H), 3.93 (s, 3H), 3.56 (t, 6.5, 2H), 2.86 (s, 3H); EIMS m/z 509 (M−CH3SO3H+); IR (neat) νmax 3330, 3099, 2933, 2874, 1725, 1649, 1592, 1537, 1502, 1466, 1411, 1369, 1306, 1238, 1174, 1127, 1076, 1048, 998, 972, 951, 833, 796, 751, 702 cm−1.
