3,5-Dichloro-2-cyanopyridine → HCID 66874911, Verbindung

HRID 1259243Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1259243
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:11])[CH3:10])=[CH:5][CH:4]=1)#[CH:2].[Cl:12][C:13]1[C:14]([C:20]#[N:21])=[N:15][CH:16]=[C:17](Cl)[CH:18]=1.CN(C=O)C.C(N(CC)CC)C>C(OCC)(=O)C.C(=O)(O)[O-].[Na+].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)I>[C:9]([C:6]1[CH:7]=[CH:8][C:3]([C:1]#[C:2][C:17]2[CH:18]=[C:13]([Cl:12])[C:14]([C:20]#[N:21])=[N:15][CH:16]=2)=[CH:4][CH:5]=1)(=[O:11])[CH3:10]

Komponenten

8

Edukt 3

HCID 27696993,5-Dichloro-2-cyanopyridineHCID 51236261-(4-Ethynylphenyl)ethan-1-oneHCID 22056947triethylamine N,N-dimethylformamide

Produkt 1

HCID 66874911HCID 66874911, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 83717Copper iodideKatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8857Ethyl AcetateLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

To a solution of 1-(4-ethynylphenyl)ethanone (commercially available) (1 eq) 3,5-dichloropicolinonitrile (1 eq), dichlorobis(triphenylphosphine)-palladium (II) (20 mol %), copper iodide (10 mol %) and DMF: Triethylamine (10:1) (0.13 M) was stirred at ambient temperature overnight. The reaction mixture was then diluted with ethyl acetate and sodium bi-carbonate solution. The two phases were separated, and the aqueous phase was extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, and concentrated en vaccuo. The crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-100% ethyl acetate in hexane and 5-((4-acetylphenyl)ethynyl)-3-chloropicolinonitrile was isolated as a yellow solid

Aufarbeitung

  1. customThe two phases were separated
  2. extractionthe aqueous phase was extracted twice with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated en vaccuo
  6. customThe crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO)
  7. customwas isolated as a yellow solid

Quellen und Nachweise

ORD-Eintrag
ord-5721af2c721b467785e05c058ef338f0
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08466167B2

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