Reacción #68469

Ecuación de reacción

Tri-t-butylphosphonium tetrafluoroborate

4-((6-bromo-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methoxy)-7-methoxyquinoline

trimethylsilyl acetylene

→

4-((6-ethynyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methoxy)-7-methoxyquinoline

Disolventes

triethylamine

dioxane

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroSealed in a tube
2. 2
   ConcentraciónConcentrated
3. 3
   workup.ADDITIONadded solid potassium carbonate (large excess)
4. 4
   FiltraciónFiltered through a plug of Celite
5. 5
   Concentraciónconcentrated
6. 6
   Filtraciónfiltered through a plug of silica gel

Procedimiento

Tri-t-butylphosphonium tetrafluoroborate (0.0377 g, 0.130 mmol), tris(dibenzylideneacetone)dipalladium (0.0594 g, 0.0649 mmol), trimethylsilyl acetylene (1.82 ml, 13.0 mmol), 4-((6-bromo-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methoxy)-7-methoxyquinoline (0.500 g, 1.30 mmol) were taken up in dioxane (10 mL) and triethylamine (3 mL). Added CuI. Sealed in a tube and heated at 80° C. for 3 h. Concentrated. Took up in MeOH and added solid potassium carbonate (large excess). Allowed to stir for 30 min. Filtered through a plug of Celite and concentrated. Took up in 10% MeOH in DCM and filtered through a plug of silica gel to afford 4-((6-ethynyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methoxy)-7-methoxyquinoline. MS m/z=331.0 [M+1]+. Calc'd for C19H14N4O2: 330.3.

Fuente