3-(2-Methoxy-4-methoxycarboxybenzyl)-5-nitroindole → Methyl 4-(5-aminoindol-3-ylmethyl)-3-methoxybenzoate

Participants

Reaction Steps

Palladium-on-carbon (10% w/w; 0.25 g.) was added to a solution of (C) (1.5 g.) in tetrahydrofuran (50 ml. ) in a hydrogenation bottle. The mixture was hydrogenated at 3.45 bars for 2 hours. The catalyst was removed by filtration through diatomaceous earth and the filtrate was evaporated. The residual oil was purified by flash chromatography on silica gel (200 ml.) eluting with 1:1 v/v ethyl acetate:hexane, to give methyl 4-(5-aminoindol-3-ylmethyl)-3-methoxybenzoate (A) (1.12 g., 82%) as a viscous oil; NMR: 3.29(br,2H,NH2), 3.88(s,3H, CO.OCH3), 3.91(s,3H, OCH3), 4.03(s,2H, CH2.Ar), 6.64(dd,1H), 6.78(m,2H), 7.10(m,2H), 7.44(m,2H), 7.68(br,1H, H1 -indole).

Provenance & Evidence