Triethylamine → HCID 58227511, compound

Participants

Reaction Steps

A solution of phenylacetylene (6.15 ml, 55.9 mmol), ethyl 2-bromothiazole-5-carboxylate (7.59 ml, 50.8 mmol), bis(triphenylphosphine)palladium(II) chloride (1.07 g, 1.52 mmol), copper (I) iodide (581 mg, 3.05 mmol), triethylamine (100 ml, 717 mmol) and tetrahydrofuran (225 mL) was stirred at 25° C. for 16 h. The reaction was worked up by concentrating to remove the THF and taken up in 400 mL of CHCl3. The CHCl3 was washed with 2×75 mL of 3.7% aq. HCl, 75 mL of brine, and dried (Na2SO4). The material was purified by silica gel chromatography using a gradient elution going from 4.5% to 8.5% EtOAc in hexanes over 30 minutes to give the titled compound, 2-phenylethynyl-thiazole-5-carboxylic acid ethyl ester (9.5 g, 73% yield), as a solid, which was used without further purification in the next step.

Provenance & Evidence