Sodium Sulfate → 3-Bromo-6-(difluoromethoxy)-2,4-dimethylpyridine

HRID 1043923Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1043923
[Br:1][C:2]1[C:3]([CH3:10])=[CH:4][C:5]([OH:9])=[N:6][C:7]=1[CH3:8].FS([C:15]([F:20])([F:19])C(O)=O)(=O)=O.S([O-])([O-])(=O)=O.[Na+].[Na+].C(=O)(O)[O-].[Na+]>C(#N)C>[Br:1][C:2]1[C:7]([CH3:8])=[N:6][C:5]([O:9][CH:15]([F:20])[F:19])=[CH:4][C:3]=1[CH3:10]

Komponenten

6

Edukt 4

HCID 24436Sodium SulfateHCID 516892Sodium BicarbonateHCID 27375162,2-Difluoro-2-(fluorosulfonyl)acetic acidHCID 178429301HCID 178429301, Verbindung

Produkt 1

HCID 866863473-Bromo-6-(difluoromethoxy)-2,4-dimethylpyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 5-bromo-4,6-dimethylpyridin-2-ol obtained in Preparation Example 23(1) (500 mg), 2-(fluorosulfonyl)difluoroacetic acid (0.307 mL) and sodium sulfate (70.3 mg) was stirred in an acetonitrile solvent (10 mL) at room temperature for 3.5 hours. A saturated aqueous sodium bicarbonate solution was added to the reaction mixture, and the mixture was then concentrated under reduced pressure. The residue was extracted with ethyl acetate, and the organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 0% to 10%) to give the title compound (68.6 mg).

Aufarbeitung

  1. concentrationthe mixture was then concentrated under reduced pressure
  2. extractionThe residue was extracted with ethyl acetate
  3. concentrationthe organic layer was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 0% to 10%)

Quellen und Nachweise

ORD-Eintrag
ord-b22ed19fc9b04cefbd85b6c79e17ca0d
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08563565B2

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