Methyl iodide → 6-chloro-3-methyl-4-(methylthio)-3H-imidazo[4,5-c]pyridine

HRID 2208991Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2208991
IC.[Cl:3][C:4]1[N:9]=[C:8]([S:10][CH3:11])[C:7]2[NH:12][CH:13]=[N:14][C:6]=2[CH:5]=1.[C:15](=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[Cl:3][C:4]1[N:9]=[C:8]([S:10][CH3:11])[C:7]2[N:12]([CH3:15])[CH:13]=[N:14][C:6]=2[CH:5]=1

Komponenten

6

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178503471HCID 178503471, Verbindung

Produkt 1

HCID 1178434146-chloro-3-methyl-4-(methylthio)-3H-imidazo[4,5-c]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Iodomethane (0.52 mL, 8.36 mmol) was added to a solution of 6-chloro-4-(methylthio)-3H-imidazo[4,5-c]pyridine 2.01 (1.40 g, 7.04 mmol) and potassium carbonate (1.95 g, 14.1 mmol) in 46 mL of DMF at room temperature. After 90 minutes, reaction mixture was taken up in ethyl acetate (150 mL) and washed with 50% saturated NaHCO3 (aq)(2×100 mL). After separating layers, aqueous was extracted with ethyl acetate (100 mL). All combined organic layers were washed with 50% brine (100 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure to yield a solid. This was purified via silica gel column chromatography (5-25% acetone in hexanes) to yield 6-chloro-3-methyl-4-(methylthio)-3H-imidazo[4,5-c]pyridine 2.02 (first eluting product).

Aufarbeitung

  1. customreaction mixture
  2. washwashed with 50% saturated NaHCO3 (aq)(2×100 mL)
  3. customAfter separating layers
  4. extractionaqueous was extracted with ethyl acetate (100 mL)
  5. washAll combined organic layers were washed with 50% brine (100 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto yield a solid
  10. customThis was purified via silica gel column chromatography (5-25% acetone in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-eec70d70a8e44b0890ce52dfc84852a6
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09376441B2

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