Diethyl Sulfate → 1-Ethyl-1H-imidazo[4,5-b]pyridine

HRID 495232Notes

Reaction equation

HRID 495232 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[N:9][C:4]=2[NH:3][CH:2]=1.[H-].[Na+].[CH2:12](OS(OCC)(=O)=O)[CH3:13]>CN(C)C=O>[CH2:12]([N:1]1[C:5]2[C:4](=[N:9][CH:8]=[CH:7][CH:6]=2)[N:3]=[CH:2]1)[CH3:13]

Participants

5

Reactant 3

HCID 6163Diethyl SulfateHCID 24758Sodium hydrideHCID 178420746HCID 178420746, compound

Product 1

HCID 217595471-Ethyl-1H-imidazo[4,5-b]pyridineYield 64.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a flask were added 0.5 g 4-azabenzimidazole and 10 ml N,N-dimethylformamide and the mixture was cooled to 10 C under nitrogen. 0.18 g Sodium hydride were added in portions and the reaction mixture was stirred for 20 minutes. 0.71 g Diethylsulfate were added and the mixture was allowed to warm to 22 C and was stirred for 16 hours. The mixture was quenched slowly with 30 ml 1M hydrochloric acid and the aqueous layer was washed with ethyl acetate. After basification with sodium hydroxide, the product was extracted twice with ethyl acetate and dried over sodium sulfate. Following filtration and solvent removal, the product was purified by silica gel chromatography using 5% methanol in ethyl acetate to 12% methanol in ethyl acetate. 0.4 g Of an oil was obtained.

Workup

  1. temperaturethe mixture was cooled to 10 C under nitrogen
  2. temperatureto warm to 22 C
  3. stirringwas stirred for 16 hours
  4. customThe mixture was quenched slowly with 30 ml 1M hydrochloric acid
  5. washthe aqueous layer was washed with ethyl acetate
  6. extractionAfter basification with sodium hydroxide, the product was extracted twice with ethyl acetate
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltration and solvent removal
  9. customthe product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-4c49b02f78144d27b0270995826ff2c6
Source dataset
uspto-grants-2009_05
Patent number
US07538931B2

Reaction notes

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