Imidazole → 265107-80-0

HRID 1502645Notes

Reaction equation

HRID 1502645 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[C:6]([C:9]1[CH:10]=[CH:11][C:12](Br)=[N:13][CH:14]=1)(=[O:8])[CH3:7].C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>CN(C)C=O.O>[C:6]([C:9]1[CH:10]=[CH:11][C:12]([N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)=[N:13][CH:14]=1)(=[O:8])[CH3:7]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 156681955-Acetyl-2-bromopyridine

Product 1

HCID 58305612265107-80-0Yield 46.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

204 mg (corresponding to 3.00 mmol) of imidazole was dissolved in 5 mL of dimethylformamide. Then, 200 mg (corresponding to 1.00 mmol) of 5-acetyl-2-bromopyridine and 414 mg (corresponding to 3.00 mmol) of potassium carbonate were added thereto. The resulting solution was heated at 100° C. for 3 hours. After the completion of the reaction, the reaction solution was cooled down to room temperature, supplemented with a saturated ammonium chloride aqueous solution and water, and extracted 3 times with dichloromethane. The combined dichloromethane layer was washed with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting crude product was purified by silica gel column chromatography (elution solvent: dichloromethane/ethyl acetate=4/1), to obtain 87 mg (corresponding to 0.462 mmol) of 5-acetyl-2-(1H-imidazole-1-yl)pyridine (FIG. 3, step 1).

Workup

  1. customAfter the completion of the reaction
  2. temperaturethe reaction solution was cooled down to room temperature
  3. extractionextracted 3 times with dichloromethane
  4. washThe combined dichloromethane layer was washed with water
  5. dry with materiala saturated saline solution, dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting crude product was purified by silica gel column chromatography (elution solvent: dichloromethane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-8d04d8733ffb4ea19d07538ed5be96c2
Source dataset
uspto-grants-2015_12
Patent number
US09211350B2

Reaction notes

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