Acetonitrile → 3,5-Dimethyl-2-phenylethynyl-3H-imidazole-4-carboxylic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

In analogy to the method as described in Chem. Pharm. Bull. 1987, 35(2), 823-828, 17.5 mg (0.025 mmol) bis-(triphenylphosphine)-palladium-II-chloride, 2.9 mg (0.015 mmol) cuprous iodide, 60.5 mg (0.6 mmol) triethylamine, 32.4 mg (0.3 mmol) ethynylbenzene and 61.8 mg (0.25 mmol) 2-bromo-3,5-dimethyl-3H-imidazole-4-carboxylic acid ethyl ester are dissolved in 1 ml DMF and shaken for 3 h at 90° C. The title compound (19.3 mg, 29%, MS: m/e=269.3, [M+H+]) was isolated from the reaction mixture by HPLC chromatography (YMC CombiPrep C18 column 50×20 mm, solvent gradient 10-95% CH3CN in 0.1 % TFA(aq) over 6.0 min, λ=230 nm, flow rate 40 ml/min).

Provenance & Evidence