Реакция #86163

Уравнение реакции

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

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

cesium carbonate

Xantphos

→

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

Выход 48.1%

Растворители

1,4-Dioxane

Условия реакции

Обработка

1. 1
   ДругоеThe resulting mixture was sealed in a pressure tube
2. 2
   ТемператураThe reaction mixture cooled to room temperature
3. 3
   Фильтрацияfiltered through Celite
4. 4
   ПромывкаThe filter cake was washed with DCM
5. 5
   КонцентрированиеThe filtrate was concentrated
6. 6
   ДругоеThe residue was purified on silica
7. 7
   Промывкаeluted with 0 to 6% MeOH in DCM

Методика

To a mixture of 6-(6-methylpyrazin-2-yl)-1H-pyrazolo[4,3-c]pyridine (1.325 mmol; 279.9 mg) and 6-bromo-3-chloro-2-fluoro-pyridine (1.988 mmol; 418.3 mg) in 1,4-Dioxane (10 mL) under Argon was added cesium carbonate (3.975 mmol; 1295 mg), Xantphos (0.2253 mmol; 130.4 mg), and tris(dibenzylideneacetone)dipalladium(0) (0.1325 mmol; 121.3 mg). The resulting mixture was sealed in a pressure tube and heated at 105° C. overnight. 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-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridine (217.1 mg, 48%).

Источник