Triethylamine → 4-[(R)-3-(2-Methyl-pyridin-4-yl)-3-oxo-1-o-tolyl-propyl]-benzoic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of (R)-3-(4-bromo-phenyl)-1-(2-methyl-pyridin-4-yl)-3-o-tolyl-propan-1-one (example 142, step 2, 100 mg) in methanol (1.5 mL) and ethyl acetate (1.5 mL) were added [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane adduct (10 mg), triethylamine (53.3 μL) at room temperature. The reaction mixture was stirred at 130° C. for 20 h under a carbon monoxide atmosphere (70 bar). A saturated aq. solution of ammonium chloride was added, the phases were separated and the inorganic one was extracted with ethyl acetate (2×). The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel (ethyl acetate/n-heptane 0:1 to 1:0) to yield the title compound as a colourless oil (95 mg, 87%), MS (ESI+): m/z=374.1 ([M+H]+).

Provenance & Evidence