Sodium Carbonate → Methyl 3-(4-(3-(thiophen-2-yl)-5-(trifluoromethyl)phenyl)oxazol-2-yl)propanoate

Participants

Reaction Conditions

Reaction Steps

A suspension of methyl 3-(4-(3-bromo-5-(trifluoromethyl)phenyl)oxazol-2-yl)propanoate (Reference Example 44, 0.454 g, 1.20 mmol), thiophene-2-boronic acid (0.230 g, 1.80 mmol) and sodium carbonate (0.954 g, 9.00 mmol) in toluene (30.0 mL) was evacuated and purged with nitrogen. To this mixture was added tetrakis(triphenylphosphine)palladium(0) (0.208 g, 0.180 mmol) and the resulting reaction mixture was heated at 100° C. for 7 h. After this time, the reaction mixture was cooled to room temperature, quenched with 1.0 M hydrochloric acid (20.0 mL), diluted with ethyl acetate and separated. The organic layer was washed with water and saturated sodium chloride, dried (Na2SO4), filtered and concentrated under reduced pressure. The resultant residue was purified by flash column chromatography (silica gel, hexanes/ethyl acetate 9:1) to provide methyl 3-(4-(3-(thiophen-2-yl)-5-(trifluoromethyl)phenyl)oxazol-2-yl)propanoate (0.145 g, 32%) as a yellow solid.

Provenance & Evidence