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Phenylacetylene → 6,7-Dichloro-2,3-dimethoxy-5-(2-phenylethynyl)quinoxaline

HRID 842687
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 842687
[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.[C:18]1([C:24]#[CH:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(N(CC)CC)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[Cl:1][C:2]1[C:3]([C:25]#[C:24][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=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
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Komponenten

6

Edukt 2

HCID 10821PhenylacetyleneHCID 106914616,7-Dichloro-2,3-dimethoxy-5-iodoquinoxaline

Produkt 1

HCID 226148926,7-Dichloro-2,3-dimethoxy-5-(2-phenylethynyl)quinoxalineAusbeute 77,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Katalysator
HCID 178418476
HCID 178418476, Verbindung
Katalysator
HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

A mixture of 6,7-dichloro-2,3-dimethoxy-5-iodoquinoxaline (Preparation 108, 5.0 g, 13 mmol), phenylacetylene (3.98 g, 39 mmol), bis(triphenylphosphine)palladium(II) chloride (0.913 g, 1.3 mmol) and copper(I) iodide (0.248 g, 1.3 mmol) in triethylamine (100 mL) was heated under reflux for 4 hours. After being cooled, the mixture was concentrated under reduced pressure and the residue partitioned between dichloromethane (200 mL) and brine (200 mL). The phases were separated and the aqueous phase extracted with dichloromethane (2×100 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 hexane:dichloromethane (1:0 changing to 1:1, by volume) to afford 6,7-dichloro-2,3-dimethoxy-5-(2-phenylethynyl)quinoxaline (3.60 g, 77%) as a yellow solid, mp 170-172° C.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hours
  3. temperatureAfter being cooled
  4. concentrationthe mixture was concentrated under reduced pressure
  5. customthe residue partitioned between dichloromethane (200 mL) and brine (200 mL)
  6. customThe phases were separated
  7. extractionthe aqueous phase extracted with dichloromethane (2×100 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-425d72f438e14f929bb299420858b8d6
Quelldatensatz
uspto-grants-2002_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06376490B1

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