Trifluoroacetic acid → 6-iodo-3-methyl-2-trifluoromethyl-3H-imidazo[4,5-b]pyridine

HRID 1775280Notes

Reaction equation

HRID 1775280 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([NH2:10])[C:5]([NH:8][CH3:9])=[N:6][CH:7]=1.[F:11][C:12]([F:17])([F:16])[C:13](O)=O>>[I:1][C:2]1[CH:3]=[C:4]2[N:10]=[C:13]([C:12]([F:17])([F:16])[F:11])[N:8]([CH3:9])[C:5]2=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 679815685-iodo-N2-methylpyridine-2,3-diamine

Product 1

HCID 1180350316-iodo-3-methyl-2-trifluoromethyl-3H-imidazo[4,5-b]pyridine

Procedure

A mixture of 0.50 g of 5-iodo-N2-methylpyridine-2,3-diamine and 6 ml of trifluoroacetic acid was stirred at room temperature for 1 hour, and then stirred under heat-reflux for 9 hours. The cooled reaction mixture was concentrated under reduced pressure, then water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, then dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was applied to a silica gel column chromatography to obtain 0.57 g of 6-iodo-3-methyl-2-trifluoromethyl-3H-imidazo[4,5-b]pyridine

Workup

  1. stirringstirred
  2. temperatureunder heat-reflux for 9 hours
  3. customThe cooled reaction mixture
  4. concentrationwas concentrated under reduced pressure
  5. additionwater was added
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe organic layer was washed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-91320df96b9a4def9ed5bb8e0bd707b4
Source dataset
uspto-grants-2016_02
Patent number
US09260436B2

Reaction notes

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