Triethylamine → HCID 54049466, compound

Participants

Reaction Conditions

Reaction Steps

2.1 g of 6-iodo-4-methoxymethyl-β-carboline-3-carboxylic acid isopropyl ester is mixed in 30 ml of dimethylformamide in succession with 1.53 ml of trimethylsilylacetylene, 15 ml of triethylamine, 50 mg of copper (I) iodide and 100 mg of tetrakis (triphenylphosphine)-palladium (O) and heated for 3 hours under argon to 60° C. solution temperature. After removal of the solvent the residue is taken up in ethyl acetate and in succession is washed with saturated sodium bicarbonate and common salt solution. The organic phase was dried, filtered and concentrated by evaporation and the residue is chromatographed on silica gel with methylene chloride:ethanol=12:1. The correspondingly combined fractions are stirred for 1 hour in 50 ml of methylene chloride with 4 ml of tetrabutylammonium fluoride at room temperature. The solution is washed with water, dried, filtered and concentrated by evaporation and the residue is chromatographed on silica gel with methylene chloride:ethanol=10:1. 830 mg of 6-ethinyl-4-methoxymethyl-β-carboline-3-carboxylic acid isopropyl ester, melting point 191°- 193° C. (ethyl acetate/hexane) is obtained by the corresponding combination of the fractions.

Provenance & Evidence