Potassium Carbonate → 1-(6-Vinylpyridin-3-YL)ethanone

HRID 535658

Reaktionsgleichung

Reaktionsgleichung von HRID 535658
Br[C:2]1[N:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.[CH:11](B1OB(C=C)OB(C=C)O1)=[CH2:12].N1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:11]([C:2]1[N:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1)=[CH2:12]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 27348062,4,6-Trivinylboroxin-Pyridine ComplexHCID 156681955-Acetyl-2-bromopyridine

Produkt 1

HCID 596367201-(6-Vinylpyridin-3-YL)ethanone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
115 °C

Versuchsvorschrift

The reaction mixture of 1-(6-bromopyridin-3-yl)ethanone (0.68 g, 3.41 mmol), 2,4,6-trivinyl-1,3,5,2,4,6-trioxatriborinane:pyridine (1:1) (0.57 g, 2.39 mmol), potassium carbonate (0.85 g, 6.14 mmol), and Pd(Ph3P)4 (0.16 g, 0.14 mmol) in acetonitrile (10 mL) was degassed with argon for 5 minutes. Then it was heated in the microwave for 30 min at 115° C. The organic phase was removed using a pipette, dried (MgSO4), filtered and concentrated and purified by flash chromatography (SiO2; heptane/EtOAc, gradient 20-80%). Yield: 0.36 g (72%).

Aufarbeitung

  1. customwas degassed with argon for 5 minutes
  2. customThe organic phase was removed
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by flash chromatography (SiO2; heptane/EtOAc, gradient 20-80%)

Quellen und Nachweise

ORD-Eintrag
ord-c90ffbba73da4c56b85a66e8591d4592
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08859534B2

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