Triethylamine → HCID 73052685, compound

Participants

Reaction Conditions

Reaction Steps

In a 10 ml Pyrex tube were dissolved (3aR,6aR)-1-(5-iodopyridin-2-yl)hexahydro-cyclopenta[b]pyrrol-2(1H)-one (107 mg, 326 μmol) in 2 ml of THF. Argon was bubbled through the solution. Ethynylbenzene (59.9 mg, 64.5 μl, 587 μmol, 1.8 equiv.), triethylamine (99.0 mg, 136 μmol, 978 μmol, 3.0 equiv.), bis(triphenylphosphine)palladium(II) chloride (13.7 mg, 19.6 μmol, 0.06 equiv.), triphenylphosphine (1.71 mg, 6.52 μmol, 0.02 equiv.), and copper (I) iodide (1.86 mg, 9.78 μmol, 0.03 equiv.) were added. The dark brown solution was stirred at 50° C. for 2 h. The residue was taken up in ethyl acetate, the solids were filtered off and washed with ethyl acetate. The filtrate was concentrated in vaccuo and the residue was purified by flash chromatography (SiO2, 20 g) using a 0% to 60% ethyl acetate in heptane gradient. One obtained 95 mg (96%) of the title compound as a viscous yellow oil, MS: m/e=303.2 (M+H+).

Provenance & Evidence