Triethylamine → Methyl 4-{1,2-dimethyl-1-[4-(1-methyl-1-pyridin-2-ylethoxy)phenyl]propyl}benzoate

Participants

Reaction Conditions

Reaction Steps

A stirred mixture of 5f (1 equiv), palladium (II) acetate (0.1 equiv.), 1,1′bis(diphenylphosphino)ferrocene (0.2 equiv) and triethylamine (2.4 equiv) in DMF/methanol (1:1) is purged with carbon monoxide for approximately 10 min and then heated to 80° C. under a carbon monoxide atmosphere (balloon). After completion of reaction, the reaction mixture is cooled to room temperature and then filtered through a short column of CELITE®, eluting copiously with EtOAc. The filtrate is poured into saturated aqueous sodium bicarbonate and extracted three times with EtOAc. The combined organic extracts are washed with water, brine, dried (Na2SO4) and concentrated in vacuo. Purification of the crude residue by flash chromatography on silica gel affords the title compound 5g.

Provenance & Evidence