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

HRID 241684
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HRID 241684 반응식
Br[C:2]1[CH:3]=[N:4][N:5]([CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][O:8]2)[CH:6]=1.[Cl:13][C:14]1[CH:19]=[C:18](B(O)O)[CH:17]=[CH:16][N:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C(Cl)Cl.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:13][C:14]1[CH:19]=[C:18]([C:2]2[CH:3]=[N:4][N:5]([CH:7]3[CH2:12][CH2:11][CH2:10][CH2:9][O:8]3)[CH:6]=2)[CH:17]=[CH:16][N:15]=1
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참가 물질

7

반응물 3

HCID 10796Cesium carbonateHCID 51515952-Chloropyridine-4-boronic acidHCID 467394664-bromo-1-(oxan-2-yl)-1H-pyrazole

생성물 1

HCID 595343552-Chloro-4-[1-(tetrahydro-pyran-2-yl)-1H-pyrazol-4-yl]-pyridine수율 43%

시약·촉매·용매 3

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
촉매
HCID 6228Dimethylformamide용매
HCID 6344Dichloromethane용매

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온도
80 °C

실험 절차

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). UPLC (Rt)=1.39 min (method M)

후처리

  1. additionwas added
  2. temperatureAfter cooling to room temperature the reaction mixture
  3. filtrationthe inorganic salts filtered off
  4. washThe filtrate was washed with water and brine
  5. customdried under Na2SO4
  6. filtrationfiltered
  7. customthe solvent was evaporated under reduced pressure
  8. customThe crude was purified by flash chromatography (20 g Isolute® silica gel cartridge; gradient elution: hexane/EtOAc from 10/0 to 8.5/1.5)

출처 및 근거

ORD 기록
ord-aa0e4954889245dc8d93035fa29dd614
출처 데이터셋
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08653075B2

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