反应详情

Combined dichloromethane solution was washed with brine and dried over Na2SO4. After removal of the solvent under reduced pressure, the crude material was separated by silica gel chromatography (2:1 hexane/ethyl acetate to 2:1 ethyl acetate/hexane) to afford the desired intermediate [1-(4-chloro-benzyl)-1H-indol-3-yl]-[4-pyridin-2-yl-5-(toluene-4-sulfonyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-2-yl]-methanol as an oil (65 mg, 30%). 1H NMR (CDCl3) δ−0.05 (s, 9H), 0.70 (t, 2h, J=6), 2.55 (s, 3H), 3.2-3.35 (m, 2H), 4.02 (d, 1H, J=7), 5.2-5.4 (m, 2H), 5.41 (s,2H), 6.4 (d, 1H), 7.0-8.0 (m, 16 H), 8.8 (d,1H, J=5). ESMS calcd for (C37H39ClN4O4SSi): 698.6; found: 699.6 (M+H)+. A solution of [1-(4-chloro-benzyl)-1H-indol-3-yl]-[4-pyridin-2-yl-5-(toluene-4-sulfonyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-2-yl]-methanol (35 mg, 50.1 mmol) in dichloromethane was treated with excess of MnO2 (0.2 g, 2.3 mmol) at room temperature for 1 hour. MnO2 was then filtered off and the filtrate was concentrated under reduced pressure. Product [1-(4-Chloro-benzyl)-1H-indol-3-yl]-[4-pyridin-2-yl-5-(toluene-4-sulfonyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-2-yl]-methanone was obtained as an oil (34.2 mg, 98%). 1H NMR (CDCl3) δ0.21 (s, 9H), 0.85 (t, 2H, J=6), 2.50 (s, 3H), 3.55 (t, 2H, J=6), 5.54 (s, 2H), 6.13 (s, 2H), 7.25-7.55 (m, 11H), 7.91 (d, 2H, J=7), 8.05 (t, 1H, J=7), 8.65 (d, 1H, J=7), 8.85 (s, 1H), 8.95 (d, 1H, J=7). ESMS calcd for (C37H37ClN4O4Ssi): 696.6; found: 697.6 (M+H)+.

1. filtrationMnO2 was then filtered off
2. concentrationthe filtrate was concentrated under reduced pressure