Water → 1-(5-bromopyridin-2-yl)-1H-imidazole-4-carbaldehyde

HRID 643005Notes

Reaction equation

HRID 643005 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[N:6][CH:7]=1.[NH:9]1[CH:13]=[C:12]([CH:14]=[O:15])[N:11]=[CH:10]1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:9]2[CH:13]=[C:12]([CH:14]=[O:15])[N:11]=[CH:10]2)=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 764281H-Imidazole-4-carbaldehydeHCID 27831685-Bromo-2-fluoropyridine

Product 1

HCID 866140051-(5-bromopyridin-2-yl)-1H-imidazole-4-carbaldehydeYield 81.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 5-bromo-2-fluoropyridine (630 mg, 3.58 mmol), 4-imidazolecarboxaldehyde (355 mg, 3.70 mmol) and K2CO3 (1.00 g, 7.25 mmol) in DMF (10 mL) was stirred at 70° C. overnight. After being cooled down, H2O was added to induce precipitation. The precipitate was collected and dried on vacuum to give 1-(5-bromopyridin-2-yl)-1H-imidazole-4-carbaldehyde (738 mg).

Workup

  1. temperatureAfter being cooled down
  2. customprecipitation
  3. customThe precipitate was collected
  4. customdried on vacuum

Sources & evidence

ORD record
ord-ac78f3b6ccee49ee9a3e7117e48e8926
Source dataset
uspto-grants-2010_04
Patent number
US07696352B2

Reaction notes

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