Реакция #1509582

Уравнение реакции

4-Bromo-1-(tetrahydro-pyran-2-yl)-1H-pyrazole

2-chloropyridine-4-boronic acid

caesium carbonate

→

title compound

Выход 43.0%

2-Chloro-4-[1-(tetrahydro-pyran-2-yl)-1H-pyrazol-4-yl]-pyridine

Выход 43.0%

Растворители

DMF

DCM

Условия реакции

Обработка

1. 1
   workup.ADDITIONwas added
2. 2
   ТемператураAfter cooling to room temperature the reaction mixture
3. 3
   Фильтрацияthe inorganic salts filtered off
4. 4
   ПромывкаThe filtrate was washed with water and brine
5. 5
   Другоеdried under Na2SO4
6. 6
   Фильтрацияfiltered
7. 7
   Другоеthe solvent was evaporated under reduced pressure
8. 8
   ДругоеThe crude was purified by flash chromatography (20 g Isolute® silica gel cartridge; gradient elution: hexane/EtOAc from 10/0 to 8.5/1.5)

Методика

4-Bromo-1-(tetrahydro-pyran-2-yl)-1H-pyrazole (0.73 g) and 2-chloropyridine-4-boronic acid (0.20 g) were dissolved in dry DMF (2 mL) under inert atmosphere and 1,1′-bis(diphenylphosphino)ferrocenedichloro palladium(II)(102 mg) was added followed by caesium carbonate (0.84 g). The mixture was heated to 80° C. and stirred for 2 h. After cooling to room temperature the reaction mixture was diluted with DCM and the inorganic salts filtered off. The filtrate was washed with water and brine, dried under Na2SO4, filtered and the solvent was evaporated under reduced pressure. The crude was purified by flash chromatography (20 g Isolute® silica gel cartridge; gradient elution: hexane/EtOAc from 10/0 to 8.5/1.5) affording the title compound (144 mg). HPLC (Rt)=1.39 min (method M)

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