Triethylamine → HCID 21249892, compound

Participants

Reaction Steps

To a solution of 1-(7-azabicyclo[2.2.1]hept-7-yl)-2-{2-(3,5-dimethylphenyl)-3-[2-(4-hydroxy-1,1-dimethyl-4-pyridin-4-yl-but-2-enylamino)ethyl]-1H-indol-5-yl}-2-methylpropan-1-one (27 mg in a mixture of 2 mL dry tetrahydrofuran and 2 mL ethyl acetate) at 0° C. was added 0.010 mL trifluoroacetic anhydride followed by 0.009 mL triethylamine and the mixture stirred at low temperature. After 15 minutes, 0.030 mL acetic acid was added and along with 28 mg palladium hydroxide on carbon. The reaction flask was fitted with a hydrogen balloon, evacuated and recharged with hydrogen (3 times) and stirred at room temperature. After 8 hours the reaction was flushed with nitrogen, filtered over diatomaceous earth and concentrated in vacuo. Purification by flash chromatography on silica gel (methylene chloride:methanol:ammonium hydroxide, 94:6:1) gave the title compound (15 mg). m/e=591 (M+H).

Provenance & Evidence