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

HRID 1750058Notes

Reaction equation

HRID 1750058 reaction equation
[CH3:1][NH:2][C:3]1[C:8]([NH2:9])=[CH:7][C:6]([C:10]([F:16])([F:15])[C:11]([F:14])([F:13])[F:12])=[CH:5][N:4]=1.[CH:17](O)=O.C(=O)(O)[O-].[Na+]>O>[CH3:1][N:2]1[C:3]2=[N:4][CH:5]=[C:6]([C:10]([F:16])([F:15])[C:11]([F:12])([F:13])[F:14])[CH:7]=[C:8]2[N:9]=[CH:17]1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 516892Sodium BicarbonateHCID 88585767N2-Methyl-5-(perfluoroethyl)pyridine-2,3-diamine

Product 1

HCID 1180352773-methyl-6-pentafluoroethyl-3H-imidazo[4,5-b]pyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.42 g of N2-methyl-5-pentafluoroethylpyridine-2,3-diamine, 4 ml of formic acid and 0.5 ml of water was stirred under heating and refluxing for 2 hours. A saturated aqueous sodium bicarbonate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium 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-pentafluoroethyl-3H-imidazo[4,5-b]pyridine.

Workup

  1. temperatureunder heating
  2. temperaturerefluxing for 2 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bc3b772baca343e8bc30ec5278850d5c
Source dataset
uspto-grants-2015_10
Patent number
US09156838B2

Reaction notes

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