methyl E-4-[5-(3-carboxyprop-1-enyl)-1-propylindol-3-ylmethyl]-3-methoxybenzoate → HCID 14882687, compound

Participants

Reaction Steps

Palladium on carbon (1.1 g, 10% w/w) was added to a solution of methyl E-4-[5-(3-carboxyprop-1-enyl)-1-propylindol-3-ylmethyl]-3-methoxybenzoate (10.8 g) in ethyl acetate (300 ml) and tetrahydrofuran (100 ml), and the mixture hydrogenated at atmospheric pressure for 6 hr. The catalyst was removed by filtration through diatomaceous earth, the filter cake washed with ethyl acetate, and the combined filtrate evaporated. The residue was stirred in 1:4 ethyl acetate:hexane (150 ml) and the product isolated by filtration to give methyl 4-[5-(3-carboxypropyl)-1-propylindol-3-ylmethyl]-3-methoxybenzoate (8.72 g, 80%) as an off-white powder; mp 106°-109°; NMR (300 MHz, DMSO-d6): 0.81(t, 3H, CH3), 1.68-1.83(m, 4H), 2.20(t, 2H), 2.61(t, 2H), 3.83(s, 3H, OCH3), 3.91(s, 3H, OCH3), 4.02(m, 4H, NCH2, ArCH2Ar'), 6.92(d, 1H), 7.08(s, 1H), 7.23(m, 2H), 7.32(d, 1H), 7.44(m, 2H).

Provenance & Evidence