Potassium Carbonate → 4-Ethenyl-3,8-difluoro-6-methoxyquinoline

HRID 638995Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 638995
Br[C:2]1[C:11]2[C:6](=[C:7]([F:14])[CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[F:15].C(=O)([O-])[O-].[K+].[K+].[CH:22](B)=[CH2:23]>COCCOC.O.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:22]([C:2]1[C:11]2[C:6](=[C:7]([F:14])[CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[F:15])=[CH2:23]

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 685768324-Bromo-3,8-difluoro-6-methoxyquinolineHCID 178419161HCID 178419161, Verbindung

Produkt 1

HCID 590260924-Ethenyl-3,8-difluoro-6-methoxyquinolineAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittel2×HCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

4-Bromo-3,8-difluoro-6-(methoxy)quinoline (0.63 g, 2.3 mmol) in DME (26 mL) under argon, was treated with tetrakis(triphenylphosphine)palladium(0) (0.13 g, 0.115 mmol) and the mixture stirred at room temperature for 20 minutes. Anhydrous potassium carbonate (0.32 g, 2.3 mmol), water (7 mL), and vinylborane:pyridine complex (see F. Kerins and D O'Shea J. Org. Chem. 2002, 67, 4968-4971) (0.22 g, 0.92 mmol) were added and the mixture was heated at 100° C. for 2 hr. It was cooled, diluted with water and extracted with ether, dried over magnesium sulfate and evaporated to dryness. After work-up the product was chromatographed on silica gel, eluting with 10% methanol in DCM to afford a white solid (0.46 g, 90%). MS (+ve ion electrospray) m/z 221 (MH+).

Aufarbeitung

  1. temperaturethe mixture was heated at 100° C. for 2 hr
  2. temperatureIt was cooled
  3. extractionextracted with ether
  4. dry with materialdried over magnesium sulfate
  5. customevaporated to dryness
  6. customAfter work-up the product was chromatographed on silica gel
  7. washeluting with 10% methanol in DCM

Quellen und Nachweise

ORD-Eintrag
ord-6d85d8f564a74eefa82a3f5dc902e62a
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07691850B2

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