Réaction #1509582

Équation de réaction

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

2-chloropyridine-4-boronic acid

caesium carbonate

→

title compound

Rendement 43.0%

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

Rendement 43.0%

Solvants

DMF

DCM

Conditions de réaction

Traitement

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

Mode opératoire

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)

Source