Acetic Acid → 5-Bromo-3-(2-chloro-4-cyanobenzyl)-2-methyl-3H-imidazo[4,5-b]pyridine

HRID 1699935Notes

Reaction equation

HRID 1699935 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([N:8]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[CH:15][C:14]=2[Cl:21])[C:9](=O)[CH3:10])[C:5]([N+:22]([O-])=O)=[CH:4][CH:3]=1.C(O)(=O)C>C(O)C.[Fe]>[Br:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[CH:15][C:14]=3[Cl:21])[C:9]([CH3:10])=[N:22][C:5]2=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 223878586-Bromo-2-(N-(2-chloro-4-cyanobenzyl)acetamido)-3-nitropyridine

Product 1

HCID 223879675-Bromo-3-(2-chloro-4-cyanobenzyl)-2-methyl-3H-imidazo[4,5-b]pyridineYield 9.9%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

To a solution of 6-bromo-2-(N-(2-chloro-4-cyanobenzyl)acetamido)-3-nitropyridine (21.8 g) in ethanol (33 ml)-acetic acid (8.3 ml) was added iron powder (2.29 g) at room temperature, and the mixture was refluxed under heating for 2 hr. The reaction mixture was cooled, the insoluble matter was removed by filtration, and the solvent was evaporated. To the residue was added dichloromethane, and the product was extracted. The solvent was evaporated and the residue was purified by silica gel column chromatography (dichloromethane/methanol=30/1) to give the objective compound (1.90 g) as a pale-yellow powder.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 2 hr
  3. temperatureThe reaction mixture was cooled
  4. customthe insoluble matter was removed by filtration
  5. customthe solvent was evaporated
  6. additionTo the residue was added dichloromethane
  7. extractionthe product was extracted
  8. customThe solvent was evaporated
  9. customthe residue was purified by silica gel column chromatography (dichloromethane/methanol=30/1)

Sources & evidence

ORD record
ord-804c74a26c1c4ec7aa2d5b79b7c429c6
Source dataset
uspto-grants-2002_02
Patent number
US06348474B1

Reaction notes

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