Trifluoroacetic acid → 4-Chloro-2-(trifluoromethyl)-1H-imidazo[4,5-c]pyridine

HRID 1863942Notes

Reaction equation

HRID 1863942 reaction equation
[Cl:1][C:2]1[C:7]([NH2:8])=[C:6]([NH2:9])[CH:5]=[CH:4][N:3]=1.[F:10][C:11]([F:16])([F:15])[C:12](O)=O>>[Cl:1][C:2]1[C:7]2[N:8]=[C:12]([C:11]([F:16])([F:15])[F:10])[NH:9][C:6]=2[CH:5]=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 2857362-Chloropyridine-3,4-diamine

Product 1

HCID 573550614-Chloro-2-(trifluoromethyl)-1H-imidazo[4,5-c]pyridine

Procedure

A mixture of 400 mg (2.79 mmol) of 2-chloropyridine-3,4-diamine [H. Dvorakova et al., Collect. Czech. Chem. Commun., 58, 629 (1993)] and a few mL of trifluoroacetic acid was stirred at reflux overnight. The cooled solution was concentrated and then re-concentrated from ethanol. Flash chromatography of the residue on silica gel [0-10% of (9:1 methanol:concentrated ammonium hydroxide solution) in dichloromethane] yielded the title compound as a foam. LC-MS 222 (M+1).

Workup

  1. temperatureat reflux overnight
  2. concentrationThe cooled solution was concentrated
  3. concentrationre-concentrated from ethanol

Sources & evidence

ORD record
ord-f9dd60c40024403187fa2ac55d702d0f
Source dataset
uspto-grants-2009_12
Patent number
US07625888B2

Reaction notes

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