반응 #57381

반응 방정식

sodium carbonate

[2-(5-bromothiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(1,1,3,3-tetramethyl-butyl)-amine

phenylacetylene

triethylamine

→

[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(1,1,3,3-tetramethyl-butyl)-amine

수율 16.2%

용매

EA

DMF

반응 조건

후처리

1. 1
   기타The phases were separated
2. 2
   추출the aqueous phase extracted with EA
3. 3
   세척The combined organic phases were washed 2× with a sat. aq. sodium carbonate solution and 2× with a sat. aq. common salt solution
4. 4
   건조dried over magnesium sulfate
5. 5
   여과After filtration and removal of the solvents under a vacuum, column chromatography (EA/DIPE/DCM 3:3:4)

실험 절차

324 mg (0.80 mmol) of [2-(5-bromothiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(1,1,3,3-tetramethyl-butyl)-amine were dissolved together with 0.11 ml (0.96 mmol) of phenylacetylene, 14 mg (0.02 mmol) of bis(triphenylphosphine)-palladium(II) chloride and 7 mg (0.04 mmol) of copper(I) iodide in DMF (6 ml) After addition of 1.1 ml (8.0 mmol) of triethylamine, the mixture was stirred at 50° C. for 2 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 2× with a sat. aq. common salt solution and dried over magnesium sulfate. After filtration and removal of the solvents under a vacuum, column chromatography (EA/DIPE/DCM 3:3:4) was carried out with the group, after which 54 mg (0.13 mmol, 16% of theoretical) of [2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(1,1,3,3-tetramethyl-butyl)-amine were obtained.

출처