Ethyl 2-bromo-1,3-thiazole-4-carboxylate → Ethyl 2-(3,4,5-trimethoxyphenylethynyl)thiazole-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

3,4,5-Trimethoxyphenylacetylene (1.34 g), ethyl 2-bromothiazole-4-carboxylate (1.98 g) and copper iodide (53 mg) were dissolved in a mixed solvent of DMF (3 mL) and triethylamine (6 mL), and to the solution dichlorobis-(triphenylphosphine)palladium (II) (99 mg) was added, and the mixture was stirred at 45° C. for 4 hours under an argon atmosphere. The reaction mixture was diluted with ethyl acetate, washed with 2 M hydrochloric acid, water and saturated brine, dried over anhydrous sodium sulfate. After concentrating the reaction mixture under reduced pressure, the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=4:1 to 3:1) to obtain the title compound.

Provenance & Evidence