Triethylamine → [2-(5-Pyridin-3-ylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-(1,1,3,3-tetramethyl-butyl)-amine

Participants

Reaction Conditions

Reaction Steps

600 mg (1.48 mmol) of [2-(5-bromothiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-(1,1,3,3-tetra-methyl-butyl)-amine were dissolved together with 183 mg (1.77 mmol) of 3-ethynylpyridine, 104 mg (0.15 mmol) of bis(triphenylphosphine)-palladium(II) chloride and 28 mg (0.15 mmol) of copper(I)-iodide in DMF (10 ml). After addition of 2.00 ml (14.78 mmol) of triethylamine, the mixture was stirred at 50° C. for 3 d. The reaction solution was then diluted with EA and combined with a sat. aq. sodium carbonate solution. The phases were separated and the aqueous phase extracted with EA. The combined organic phases were washed 2× with a sat. aq. sodium carbonate solution and dried over sodium sulfate. After filtration and removal of the solvents under a vacuum, column chromatography (EA) was carried out with the group. After crystallisation of the resultant crude product, 310 mg (0.72 mmol, 49% of theoretical) of [2-(5-pyridin-3-ylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-(1,1,3,3-tetramethyl-butyl)-amine were obtained.

Provenance & Evidence