Ethyl Acetate → HCID 67834674, compound

Participants

Reaction Steps

A mixture of E-α-methyl-N-propylindol-5-acrylamide (1.75 g) and silver carbonate (1.99 g) in dry toluene (30 ml) was stirred and heated under reflux for 18 hr, under an atmosphere of nitrogen. The mixture was cooled to 80°, methyl 4-bromomethyl-3-methoxybenzoate (2.06 g) added, and the mixture stirred at 85° for 15 hours. The mixture was cooled, ethyl acetate (50 ml) added, the salts were removed by filtration through diatomaceous earth, the filter pad was washed with ethyl acetate, and the filtrate evaporated. The product was purified by flash chromatography, eluting with 5:2:3 hexane:methylene chloride:ethyl acetate, to give methyl E-3-methoxy-4-[5-[2-(propylcarbamoyl)-1-propenyl]indol-3-ylmethyl]benzoate (1.62 g, 53%) as a solid foam; mp 55°-60°; partial NMR (250 MHz, DMSO-d6): 0.87(t, 3H, CH2CH2CH3), 1.47(m, 2H, CH2CH2CH3), 1.99 (d, J=0.98 Hz, 3H, CCH3), 3.10(m, 2H, CH2CH2CH3), 3.82(s, 3H, OCH3), 3.91(s, 3H, OCH3), 4.05(s, 2H, ArCH2Ar'), 7.93(br t, NHCO), 11.0(br s, 1H, H1 -indole).

Provenance & Evidence