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,2 H,NH2), 3.88 (s,3 H, CO.OCH3), 3.91 (s,3 H, OCH3), 4.03 (s,2 H, CH2.Ar), 6.64 (dd,1 H), 6.78 (m,2 H), 7.10 (m,2 H), 7.44 (m,2 H), 7.68 (br,1 H, H1 -indole).

Provenance & Evidence