Reacción #1509582

Ecuación de reacción

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

2-chloropyridine-4-boronic acid

caesium carbonate

→

title compound

Rendimiento 43.0%

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

Rendimiento 43.0%

Disolventes

DMF

DCM

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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)

Fuente