Potassium Carbonate → 6,7-Dichloro-2,3-dimethoxy-5-(3-pyridyl)quinoxaline

HRID 842686Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 842686
[Cl:1][C:2]1[C:3](I)=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[N:8]=[C:7]([O:13][CH3:14])[C:6]([O:15][CH3:16])=[N:5]2.[N:18]1[CH:23]=[CH:22][CH:21]=[C:20](B(O)O)[CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.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>[Cl:1][C:2]1[C:3]([C:20]2[CH:19]=[N:18][CH:23]=[CH:22][CH:21]=2)=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[N:8]=[C:7]([O:13][CH3:14])[C:6]([O:15][CH3:16])=[N:5]2

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 27343783-Pyridinylboronic acidHCID 106914616,7-Dichloro-2,3-dimethoxy-5-iodoquinoxaline

Produkt 1

HCID 226149136,7-Dichloro-2,3-dimethoxy-5-(3-pyridyl)quinoxalineAusbeute 29,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of 6,7-dichloro-2,3-dimethoxy-5-iodoquinoxaline (Preparation 108, 0.2 g, 0.519 mmol), 3-pyridylboronic acid (Rec. Trav. Chim. Pays-Bas. 84, 439 (1965)) (0.077 g, 0.623 mmol), tetrakis(triphenylphosphine)palladium(0) (0.03 g, 0.026 mmol) and potassium carbonate (0.143 g, 1.038 mmol) in 1,4-dioxane (12 mL) and water (4 mL) was heated under reflux for 16 hours. After being cooled, the mixture was concentrated under reduced pressure and the residue partitioned between ethyl acetate (20 mL) and water (20 mL). The phases were separated and the aqueous phase extracted with ethyl acetate (2×40 mL). The combined organic extracts were dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel, by gradient elution using dichloromethane:methanol (1:0 changing to 99:1, by volume) to afford the title compound (0.051 g, 29%) as a yellow solid.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 16 hours
  3. temperatureAfter being cooled
  4. concentrationthe mixture was concentrated under reduced pressure
  5. customthe residue partitioned between ethyl acetate (20 mL) and water (20 mL)
  6. customThe phases were separated
  7. extractionthe aqueous phase extracted with ethyl acetate (2×40 mL)
  8. dry with materialThe combined organic extracts were dried (MgSO4)
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by flash chromatography on silica gel, by gradient elution

Quellen und Nachweise

ORD-Eintrag
ord-cf07ab76efd34949ac750994c8f08691
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06376490B1

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