Triethylamine → Methyl 3-(4-(3-methyl-5-(trifluoromethyl)phenyl)oxazol-2-yl)propanoate

Participants

Reaction Conditions

Reaction Steps

A stirred solution of methyl 3-(4-(3-bromo-5-(trifluoromethyl)phenyl)oxazol-2-yl)propanoate (Reference Example 44, 0.150 g, 0.397 mmol), methylboronic acid (0.071 g, 1.19 mmol), and triethylamine (0.402 g, 3.97 mmol) in DMF (10.0 mL) was degassed and then purged with nitrogen. To this reaction mixture was added tetrakis(triphenylphosphine)palladium(0) (0.024 g, 0.0203 mmol) and the resulting reaction mixture was heated at 100° C. for 6 h. After this time, the mixture was cooled to room temperature, diluted with ethyl acetate (50 mL), washed with water and saturated sodium chloride, dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel, hexanes/ethyl acetate 9:1) to provide methyl 3-(4-(3-methyl-5-(trifluoromethyl)phenyl)oxazol-2-yl)propanoate (0.097 g, 78%) as a viscous yellow oil.

Provenance & Evidence