反应详情

Silver(I) oxide (4.92 g) was added to a solution of indole (F) (2.05 g) in toluene (15 ml). The mixture was protected from light, stirred, and heated to reflux under an atmosphere of nitrogen for 24 hours. A solution of methyl 4-bromomethyl-3-methoxybenzoate (B) (2.31 g) in toluene (5 ml) was added, and stirring was continued at 95° C. for 4 hours. The mixture was then diluted with ethyl acetate and filtered. The filtrate was evaporated to give an amber gum which was purified by flash chromatography on silica gel (862 ml), eluting with 1:99 v/v methanol:chloroform to give (E) (0.47 g, 13%) as a white foam; partial NMR (80 MHz, CDCl3): 0.92[d, 6H, CH(CH3)2], 3.40(q, 2H, NCH2), 3.87(s, 3H, OCH3), 4.09(s, 2H, ArCH2), 6.18(br t, 1H, CONH), 7.98(br s, 1H, H4 -indole), 8.84(br s, 1; H, NH).

1. temperatureheated
2. temperatureto reflux under an atmosphere of nitrogen for 24 hours
3. stirringstirring
4. filtrationfiltered
5. customThe filtrate was evaporated
6. customto give an amber gum which
7. customwas purified by flash chromatography on silica gel (862 ml)
8. washeluting with 1:99 v/v methanol