Sodium Carbonate → 4-[5-(4-Chloro-phenyl)-pyridin-2-yl]-2-methyl-but-3-yn-2-ol

HRID 1916724

Reaktionsgleichung

Reaktionsgleichung von HRID 1916724
C([O-])([O-])=O.[Na+].[Na+].Br[C:8]1[CH:9]=[CH:10][C:11]([C:14]#[C:15][C:16]([CH3:19])([OH:18])[CH3:17])=[N:12][CH:13]=1.[Cl:20][C:21]1[CH:26]=[CH:25][C:24](OB(O)O)=[CH:23][CH:22]=1>O1CCOCC1>[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([C:8]2[CH:9]=[CH:10][C:11]([C:14]#[C:15][C:16]([CH3:19])([OH:18])[CH3:17])=[N:12][CH:13]=2)=[CH:23][CH:22]=1

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 17810664p-Chlorophenylboric acidHCID 225024714-(5-Bromo-pyridin-2-yl)-2-methyl-but-3-yn-2-ol

Produkt 1

HCID 690774524-[5-(4-Chloro-phenyl)-pyridin-2-yl]-2-methyl-but-3-yn-2-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

Under an argon atmosphere 3 mL 2 M Na2CO3 solution and 173 mg (0.15 mmol) tetrakis-triphenylphosphane-palladium are added to a solution of 720 mg (3.0 mmol) 4-(5-bromo-pyridin-2-yl)-2-methyl-but-3-yn-2-ol and 593 mg (3.6 mmol) 4-chlorophenyl-boric acid in 60 mL 1,4-dioxane and the reaction mixture is stirred for 18 h at 85° C. The mixture is evaporated down i. vac., the residue is combined with water, extracted exhaustively with EtOAc, the organic phase is washed with water and dried over Na2SO4. After the desiccant and solvent have been eliminated the residue is purified by chromatography (silica gel, PE/EtOAc 1:1).

Aufarbeitung

  1. customThe mixture is evaporated down i
  2. extractionextracted exhaustively with EtOAc
  3. washthe organic phase is washed with water
  4. dry with materialdried over Na2SO4
  5. customis purified by chromatography (silica gel, PE/EtOAc 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-3f069d70169b475c9c67d3df485d8442
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08618132B2

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