Methanol → HCID 178502068, Verbindung

HRID 70248

Reaktionsgleichung

Reaktionsgleichung von HRID 70248
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[CH:9])=[CH:4][C:3]=1[CH2:10][NH:11][C:12](=[O:15])[O:13][CH3:14].CO.C[Si]([N:22]=[N+:23]=[N-:24])(C)C>CN(C)C=O.[Cu]I>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:24][N:23]=[N:22][CH:9]=2)=[CH:4][C:3]=1[CH2:10][NH:11][C:12](=[O:15])[O:13][CH3:14]

Komponenten

6

Edukt 3

HCID 887MethanolHCID 78378AzidotrimethylsilaneHCID 86641518methyl N-[(2-chloro-5-ethynylphenyl)methyl]carbamate2×

Produkt 1

HCID 178502068HCID 178502068, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of methyl N-[(2-chloro-5-ethynylphenyl)methyl]carbamate (i.e. the product of Step D) (0.43 g, 1.92 mmol) in N,N-dimethylformamide (3.9 mL) and methanol (0.4 mL) was added trimethylsilyl azide (0.38 mL, 2.89 mmol) and copper(I) iodide (0.019 g, 0.1 mmol). The reaction mixture was heated in a CEM Discover microwave apparatus at 100° C. for 8 h and then allowed to cool to room temperature. The reaction mixture was partitioned between ethyl acetate and aqueous sodium chloride, the layers were separated and the aqueous layer was extracted with ethyl acetate (2×). The combined organic layers were washed with water (3×), dried over magnesium sulfate, filtered and concentrated under reduced pressure to provide the title compound, a compound of the present invention, as a brown solid (0.30 g).

Aufarbeitung

  1. temperatureto cool to room temperature
  2. customThe reaction mixture was partitioned between ethyl acetate and aqueous sodium chloride
  3. customthe layers were separated
  4. extractionthe aqueous layer was extracted with ethyl acetate (2×)
  5. washThe combined organic layers were washed with water (3×)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-35a6f0c7e97740369673e373933633cd
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822521B2

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