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

HRID 2283492ノート

反応式

HRID 2283492 の反応式
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

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 178477754HCID 178477754、化合物触媒HCID 962Water溶媒2 回HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-495f013eb1e94076b94720a400f687f2
出典データセット
uspto-grants-2015_09
特許番号
US09145391B2

反応ノート

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