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

HRID 2208991Notes

Reaction equation

HRID 2208991 reaction equation
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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-eec70d70a8e44b0890ce52dfc84852a6
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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