2-Aminopyridine → 2-(4'-Bromo-biphenyl-4-yl)-imidazo [1,2-a] pyridine

HRID 251771Notes

Reaction equation

HRID 251771 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)=O.[NH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1.C(=O)([O-])O.[Na+]>C(O)C>[Br:17][C:14]1[CH:15]=[CH:16][C:11]([C:8]2[CH:9]=[CH:10][C:5]([C:3]3[N:18]=[C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][N:20]4[CH:2]=3)=[CH:6][CH:7]=2)=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 104392-AminopyridineHCID 516892Sodium BicarbonateHCID 32747482-Bromo-1-(4'-bromo-1,1'-biphenyl-4-yl)ethanone

Product 1

HCID 230885342-(4'-Bromo-biphenyl-4-yl)-imidazo [1,2-a] pyridineYield 84%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Dissolving 6.7 g (19 mmol) of 2-bromo-1-(4′-bromo-biphenyl-4-yl)-ethanone into 50 milliliter of ethanol, adding 2.1 g (22 mmol) of 2-aminopyridine and 5.0 g of sodium hydrogen carbonate, the resultant suspension was refluxed under heating for 7 hours. After completion of the reaction, separation with filtration was carried out and resultant crystals were washed with water and methanol, thereby obtaining yellow crystals of 2-(4′-bromo-biphenyl-4-yl)-imidazo [1,2-a] pyridine in an amount of 5.5 g (yield: 84%).

Workup

  1. temperatureunder heating for 7 hours
  2. customAfter completion of the reaction, separation
  3. filtrationwith filtration
  4. washresultant crystals were washed with water and methanol

Sources & evidence

ORD record
ord-5eef668c5add4ed582770741a23436eb
Source dataset
uspto-grants-2011_01
Patent number
US07867629B2

Reaction notes

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