تفاعل #1509582

معادلة التفاعل

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

2-chloropyridine-4-boronic acid

caesium carbonate

→

title compound

المردود 43.0%

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

المردود 43.0%

المذيبات

DMF

DCM

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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)

المصدر