Triethylamine → [2-(3-Hexyl-phenyl)-3-methyl-5-trimethylsilanylethynyl-3H-imidazol-4-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone

Participants

Reaction Steps

To a suspension of 0.55 g (1.00 mmol) of [2-(3-hexyl-phenyl)-5-iodo-3-methyl-3H-imidazol-4-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone (example 2), 0.057 g (0.3 mmol) of copper(I) iodide, 0.117 g (0.1 mmol) of tetrakis-(triphenylphosphine)-palladium and 1.134 g (3.00 mmol) of tetrabutylammoniumiodide in 10 ml of DMF were added 2.027 ml=1.471 g (14.5 mmol) of Et3N. After stirring at RT for 30 min, 0.57 ml=0.394 g (4.0 mmol) of trimethylsilylacetylene were added and the reaction was heated up to 70° C. for 1 hour and subsequently cooled down to RT. The reaction mixture was then poured into crashed ice and extracted twice with EtOAc; the organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography (CH2Cl2/MeOH 1:0 to 9:1) to give 0.52 (100%) of the title compound as brown oil. MS: 519.4 (MH+).

Provenance & Evidence