Triethylamine → HCID 54355981, compound

Participants

Reaction Steps

In a pressure vessel, 1.08 g (3 mmol) of 6-iodo-4-methyl-β-carboline-3-carboxylic acid ethyl ester is heated to 140° C. for 3 hours with 72 mg (0.06 mmol) of palladium(II) acetate, 0.48 ml (3.6 mmol) of triethylamine, and 432 mg (4.5 mmol) of 2-cyclohexen-1-one in 10 ml of absolute dimethylformamide. After concentration, the mixture is chromatographed over silica gel with methylene chloride:ethanol=10:2. After recrystallization of the combined polar fractions from methylene chloride/cyclohexane, 75 mg (6.7% of theory) of 6-(1-oxo-2-cyclohexen-3-yl)-4-methyl-β-carboline-3-carboxylic acid ethyl ester is obtained, mp 245°-248° C. After recrystallization from ethyl acetate, the combined nonpolar fractions, which are chromatographed twice over silica gel with toluene:glacial acetic acid:water=10:10:1, yield 60 mg (5.8% of theory) of 6-(1-oxocyclohex-3-yl)-4-methyl-β-carboline-3-carboxylic acid ethyl ester, mp 182°-189° C.

Provenance & Evidence