Reaktion #1509582

Reaktionsgleichung

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

2-chloropyridine-4-boronic acid

caesium carbonate

→

title compound

Ausbeute 43.0%

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

Ausbeute 43.0%

Lösungsmittel

DMF

DCM

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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)

Quelle