p-Bromoacetophenone → 2-(4-Bromophenyl)imidazo[1,2-a]pyridine

HRID 251761Notes

Reaction equation

HRID 251761 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([Br:10])=[CH:6][CH:5]=1)=O.[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1.[OH-].[Na+]>C(O)C>[Br:10][C:7]1[CH:8]=[CH:9][C:4]([C:2]2[N:11]=[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]3[CH:1]=2)=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 7466p-BromoacetophenoneHCID 104392-AminopyridineHCID 14798Sodium Hydroxide

Product 1

HCID 6234162-(4-Bromophenyl)imidazo[1,2-a]pyridineYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Dissolving 15 g (54 mmol) of 4-bromoacetophenone and 5.2 g (55 mmol) of 2-aminopyridine into 100 milliliter of ethanol, adding 7.0 g of sodium hydroxide, the resultant suspension was refluxed under heating for 6 hours. After completion of the reaction, resultant crystals were separated with filtration, washed with water and ethanol, thereby obtaining 12.5 g of 2-(4-bromo-phenyl)-imidazo [1,2-a] pyridine (yield: 85%).

Workup

  1. temperatureunder heating for 6 hours
  2. customAfter completion of the reaction
  3. customresultant crystals were separated with filtration
  4. washwashed with water and ethanol

Sources & evidence

ORD record
ord-51c6f98e38224fa1b37f06b79058030e
Source dataset
uspto-grants-2011_01
Patent number
US07867629B2

Reaction notes

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