Reacción #86216

Ecuación de reacción

6-(6-methylpyrazin-2-yl)-1H-pyrazolo[4,3-c]pyridine

(6-bromo-2-fluoro-3-pyridyl)methanol

potassium carbonate

N,N′-Dimethylethylenediamine

→

[2-fluoro-6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-3-pyridyl]methanol

Rendimiento 12.0%

Disolventes

1,4-Dioxane

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrowas purged with Argon
2. 2
   Otrothen sealed in a pressure tube
3. 3
   TemperaturaThe mixture was cooled to room temperature
4. 4
   Filtraciónfiltered through Celite
5. 5
   ConcentraciónThe filtrate was concentrated
6. 6
   Otrothe residue was purified on silica
7. 7
   Lavadoeluted with 0 to 100% EtOAc in Heptane

Procedimiento

A mixture of 6-(6-methylpyrazin-2-yl)-1H-pyrazolo[4,3-c]pyridine (2.000 mmol; 422.4 mg), (6-bromo-2-fluoro-3-pyridyl)methanol (2.400 mmol; 494.4 mg), potassium carbonate (4.000 mmol; 552.8 mg), copper(I) iodide (2.000 mmol; 380.9 mg), and N,N′-Dimethylethylenediamine (0.2000 mmol; 17.81 mg; 0.0217 mL) in 1,4-Dioxane (15 mL) was purged with Argon then sealed in a pressure tube and heated at 105° C. overnight. The mixture was cooled to room temperature and filtered through Celite. The filtrate was concentrated and the residue was purified on silica eluted with 0 to 100% EtOAc in Heptane to afford [2-fluoro-6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-3-pyridyl]methanol (79.5 mg, 12%).

Fuente