Reacción #322369

Ecuación de reacción

6-bromo-2-quinolinecarboxaldehyde

1-decyne

triethylamine

→

product

Rendimiento 64.0%

6-(1-Decynyl)-2-quinolinecarboxaldehyde

Rendimiento 64.0%

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrodegassed, under nitrogen
2. 2
   workup.ADDITIONbis(Triphenylphosphine)palladium (II) chloride (0.56 g) and copper (I) iodide (0.08 g) were added to the reaction mixture, which
3. 3
   Otrowas degassed
4. 4
   Temperaturaheated at 40° C. for 19 hrs
5. 5
   TemperaturaThe mixture was cooled to room temperature
6. 6
   Filtraciónthe precipitate was filtered
7. 7
   Lavadothe filter cake was washed with ethyl acetate
8. 8
   Otrothe filtrate was evaporated
9. 9
   workup.DISSOLUTIONThe residue was dissolved in ethyl acetate
10. 10
    Lavadowashed with water and brine
11. 11
    Secadodried over anhydrous magnesium sulfate
12. 12
    Filtraciónfiltered
13. 13
    Concentraciónthe filtrate was concentrated
14. 14
    OtroThe residue was chromatographed on silica gel
15. 15
    Lavadoeluting with heptane to heptane
16. 16
    OtroThe appropriate fractions were collected
17. 17
    Otroevaporated
18. 18
    OtroA 2 g-portion of the residue (23.4 g) was chromatographed
19. 19
    Lavadoeluting with hexane

Procedimiento

A solution of 6-bromo-2-quinolinecarboxaldehyde (18.9 g), 1-decyne (12.2 g) and triethylamine (24.3 g) in dry tetrahydrofuran (300 ml) was chilled to 5° C. and degassed, under nitrogen. bis(Triphenylphosphine)palladium (II) chloride (0.56 g) and copper (I) iodide (0.08 g) were added to the reaction mixture, which was degassed and stirred under nitrogen at room temperature for 30 mins, and then heated at 40° C. for 19 hrs. The mixture was cooled to room temperature, the precipitate was filtered, and the filter cake was washed with ethyl acetate, and the filtrate was evaporated. The residue was dissolved in ethyl acetate, washed with water and brine, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated. The residue was chromatographed on silica gel, eluting with heptane to heptane:2% ethyl acetate. The appropriate fractions were collected and evaporated. A 2 g-portion of the residue (23.4 g) was chromatographed, eluting with hexane:dichloromethane/2:1 give 1.3 g (64.0%) of product, mp 46.5°-47.5° C.

Fuente