Reaction #1509582

Reaction equation

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

2-chloropyridine-4-boronic acid

caesium carbonate

→

title compound

Yield 43.0%

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

Yield 43.0%

Solvents

DMF

DCM

Conditions

Workup

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

Procedure

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