Formic Acid → 3-methyl-6-trifluoromethylsulfanyl-3H-imidazo[4,5-b]pyridine

HRID 1750054Notes

Reaction equation

HRID 1750054 reaction equation
[CH3:1][NH:2][C:3]1[C:8]([NH2:9])=[CH:7][C:6]([S:10][C:11]([F:14])([F:13])[F:12])=[CH:5][N:4]=1.[CH:15](O)=O>O>[CH3:1][N:2]1[C:3]2=[N:4][CH:5]=[C:6]([S:10][C:11]([F:12])([F:14])[F:13])[CH:7]=[C:8]2[N:9]=[CH:15]1

Participants

4

Reactant 2

HCID 284Formic AcidHCID 68091243N2-methyl-5-trifluoromethylsulfanylpyridine-2,3-diamine

Product 1

HCID 1180355783-methyl-6-trifluoromethylsulfanyl-3H-imidazo[4,5-b]pyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 10.0 g of N2-methyl-5-trifluoromethylsulfanylpyridine-2,3-diamine, 41 ml of formic acid and 5 ml of water was stirred under heating and refluxing for 2 hours. The reaction mixture was concentrated under reduced pressure, a saturated aqueous sodium bicarbonate solution was added to the resulting residue, and the mixture was extracted with methyl-tert-butyl ether. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was applied to a silica gel column chromatography to obtain 7.80 g of 3-methyl-6-trifluoromethylsulfanyl-3H-imidazo[4,5-b]pyridine.

Workup

  1. temperatureunder heating
  2. temperaturerefluxing for 2 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additiona saturated aqueous sodium bicarbonate solution was added to the resulting residue
  5. extractionthe mixture was extracted with methyl-tert-butyl ether
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-34888e2238df453ebbb53cd0d7c9435f
Source dataset
uspto-grants-2015_10
Patent number
US09156838B2

Reaction notes

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