Ethyl Acetate → ethyl {3-[1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl]phenyl}acetate

HRID 2283492노트

반응식

HRID 2283492 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.CC1(C)C(C)(C)OB([C:21]2[CH:22]=[C:23]([CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH:24]=[CH:25][CH:26]=2)O1.C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C>O1CCOCC1.O.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Fe]>[O:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH:7]1[N:5]1[CH:6]=[C:2]([C:25]2[CH:24]=[C:23]([CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH:22]=[CH:21][CH:26]=2)[CH:3]=[N:4]1

참가 물질

8

반응물 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 467394664-bromo-1-(oxan-2-yl)-1H-pyrazoleHCID 53217140Ethyl 2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetate

생성물 1

HCID 86731997ethyl {3-[1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl]phenyl}acetate

시약·촉매·용매 3

HCID 178477754HCID 178477754, 화합물촉매HCID 962Water용매2회HCID 312751,4-Dioxane용매

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온도
80 °C

실험 절차

A mixture of 4-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole (5 g, 21.6 mmol), ethyl [3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetate (6.5 g, 22.7 mmol), sodium carbonate (7 g, 64.8 mmol) and [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.513 g, 0.648 mmol) in dioxane (60 mL) and water (30 mL) was stirred at 80° C. for 14 hours. After allowing to cool to room temperature, ethyl acetate and water were added to the mixture, and the resultant mixture was filtered. The organic layer was separated, washed with brine, dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to afford ethyl {3-[1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl]phenyl}acetate as an oil.

후처리

  1. temperatureto cool to room temperature
  2. filtrationthe resultant mixture was filtered
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-495f013eb1e94076b94720a400f687f2
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09145391B2

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