Potassium Hydroxide → N-((6-(5-(But-3-enyloxy)-2,4-dimethylphenyl)pyridin-2-yl)methylene)-2,6-diisopropylaniline

HRID 2047949Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2047949
Br[C:2]1[N:7]=[C:6]([CH:8]=[N:9][C:10]2[C:15]([CH:16]([CH3:18])[CH3:17])=[CH:14][CH:13]=[CH:12][C:11]=2[CH:19]([CH3:21])[CH3:20])[CH:5]=[CH:4][CH:3]=1.[CH2:22]([O:26][C:27]1[C:28]([CH3:37])=[CH:29][C:30]([CH3:36])=[C:31](B(O)O)[CH:32]=1)[CH2:23][CH:24]=[CH2:25].[OH-].[K+]>[Br-].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.[Pd+].C1COCC1>[CH2:22]([O:26][C:27]1[C:28]([CH3:37])=[CH:29][C:30]([CH3:36])=[C:31]([C:2]2[N:7]=[C:6]([CH:8]=[N:9][C:10]3[C:15]([CH:16]([CH3:18])[CH3:17])=[CH:14][CH:13]=[CH:12][C:11]=3[CH:19]([CH3:21])[CH3:20])[CH:5]=[CH:4][CH:3]=2)[CH:32]=1)[CH2:23][CH:24]=[CH2:25]

Komponenten

6

Edukt 3

HCID 14797Potassium HydroxideHCID 594796125-(But-3-enyloxy)-2,4-dimethylphenylboronic acidHCID 59479616N-[(6-Bromo-2-pyridinyl)methylene]-2,6-bis(1-methylethyl)benzenamine

Produkt 1

HCID 59479617N-((6-(5-(But-3-enyloxy)-2,4-dimethylphenyl)pyridin-2-yl)methylene)-2,6-diisopropylaniline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178454878HCID 178454878, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

In the glovebox, N-((6-bromopyridin-2-yl)methylene)-2,6-diisopropylaniline (1.392 g, 4.03 mmol) is combined with 5-(but-3-enyloxy)-2,4-dimethylphenylboronic acid (1.000 g, 4.03 mmol) and KOH (0.678 g, 12.1 mmol) and dry THF (40 mL) is added. Palladium(I) tri-tert-butylphosphine bromide, dimer [PtBu3)PdBr]2 (0.062 g, 0.040 mmol) is added and the reaction mixture is stirred for five hours, removed from the glovebox, and ether (100 mL) is added. The solution is washed with water (50 mL) and then brine (50 mL), dried over magnesium sulfate, filtered, and solvents removed by evaporation. Yield=1.86 g of orange sticky oil. The product is used without further purification.

Aufarbeitung

  1. additionis added
  2. customremoved from the glovebox, and ether (100 mL)
  3. additionis added
  4. washThe solution is washed with water (50 mL)
  5. dry with materialbrine (50 mL), dried over magnesium sulfate
  6. filtrationfiltered
  7. customsolvents removed by evaporation
  8. customThe product is used without further purification

Quellen und Nachweise

ORD-Eintrag
ord-8a50c24fee944aaf8504f487d0ca5fe4
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08592615B2

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