Phenacyl bromide → 6-Bromo-2-phenylimidazo[1,2-a]pyridine

HRID 251772Notes

Reaction equation

HRID 251772 reaction equation
[CH2:1](Br)[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=O.[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][N:13]=1.C(=O)([O-])O.[Na+]>C(O)C>[Br:18][C:15]1[CH:16]=[CH:17][C:12]2[N:13]([CH:1]=[C:2]([C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)[N:11]=2)[CH:14]=1

Participants

5

Reactant 3

HCID 6259Phenacyl bromideHCID 706222-Amino-5-bromopyridineHCID 516892Sodium Bicarbonate

Product 1

HCID 6234306-Bromo-2-phenylimidazo[1,2-a]pyridineYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Dissolving 5.8 g (29 mmol) of phenacyl bromide and 5.0 g (29 mmol) of 2-amino-5-bromopyridine into 50 milliliter of ethanol, adding 3.6 g of sodium hydrogen carbonate, the resultant suspension was refluxed under heating for 6 hours. After completion of the reaction, separation with filtration was carried out and resultant crystals were washed with water and ethanol, thereby obtaining 6.4 g of 6-bromo-2-phenyl-imidazo [1,2-a] pyridine (yield: 81%).

Workup

  1. temperatureunder heating for 6 hours
  2. customAfter completion of the reaction, separation
  3. filtrationwith filtration
  4. washresultant crystals were washed with water and ethanol

Sources & evidence

ORD record
ord-ec6f08cadf0f45ebbda18c1b1ca535b5
Source dataset
uspto-grants-2011_01
Patent number
US07867629B2

Reaction notes

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