Reacción #86107

Ecuación de reacción

6-(5-ethyl-3-pyridyl)-1H-pyrazolo[4,3-c]pyridine

6-bromo-3-chloro-2-fluoro-pyridine

cesium carbonate

Xantphos

→

1-(5-chloro-6-fluoro-2-pyridyl)-6-(5-ethyl-3-pyridyl)pyrazolo[4,3-c]pyridine

Rendimiento 59.0%

Disolventes

1,4-Dioxane

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe resulting mixture was sealed in a pressure tube
2. 2
   TemperaturaThe reaction mixture cooled to room temperature
3. 3
   Filtraciónfiltered through Celite
4. 4
   LavadoThe filter cake was washed with DCM
5. 5
   ConcentraciónThe filtrate was concentrated
6. 6
   OtroThe residue was purified on silica
7. 7
   Lavadoeluted with 0 to 6% MeOH in DCM

Procedimiento

To a solution of the aforesaid 6-(5-ethyl-3-pyridyl)-1H-pyrazolo[4,3-c]pyridine (0.264 mmol; 95.9 mg) and 6-bromo-3-chloro-2-fluoro-pyridine (0.396 mmol; 83.4 mg) in 1,4-Dioxane (10 mL) under Nitrogen was added cesium carbonate (0.528 mmol; 172 mg), Xantphos (0.0449 mmol; 26.0 mg), and Tris(dibenzylideneacetone)dipalladium(0) (0.0264 mmol; 24.2 mg). The resulting mixture was sealed in a pressure tube and heated at 100° C. for 17 hours. The reaction mixture cooled to room temperature, and filtered through Celite. The filter cake was washed with DCM. The filtrate was concentrated. The residue was purified on silica eluted with 0 to 6% MeOH in DCM to afford 1-(5-chloro-6-fluoro-2-pyridyl)-6-(5-ethyl-3-pyridyl)pyrazolo[4,3-c]pyridine (54.9 mg, 59%).

Fuente