Propargyl alcohol → 3-[4-(3-Hydroxy-prop-1-ynyl)-phenyl]-1-(2-methyl-pyridin-4-yl)-3-o-tolyl-propan-1-one

Participants

Reaction Steps

To 3-(4-bromo-phenyl)-1-(2-methyl-pyridin-4-yl)-3-o-tolyl-propan-1-one ((example 74, step 5), 400 mg) in triethylamine (4.1 mL) tetrakis(triphenylphosphine)palladium (59 mg) and CuI (10 mg) were added. At 80° C. 2-propyn-1-ol (0.12 mL) was added slowly, and the solution was stirred at that temperature for 3 hours. The solution was concentrated in vacuo and redissolved in EtOAc and a saturated solution of NH4Cl. The phases were separated and the inorganic one extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel (EtOAc/n-heptane 2:1) to yield the title compound (264 mg, 70%) as a yellow oil, MS (ESI+): m/z=370.1 ([M+H]+).

Provenance & Evidence