2-Butanone, 3-bromo- → 6,8-Dibromo-2,3-dimethylimidazo[1,2-a]pyridine

HRID 1354165Notes

Reaction equation

HRID 1354165 reaction equation
[NH2:1][C:2]1[C:7]([Br:8])=[CH:6][C:5]([Br:9])=[CH:4][N:3]=1.Br[CH:11]([CH3:15])[C:12](=O)[CH3:13]>O1CCCC1>[Br:9][C:5]1[CH:6]=[C:7]([Br:8])[C:2]2[N:3]([C:11]([CH3:15])=[C:12]([CH3:13])[N:1]=2)[CH:4]=1

Participants

4

Reactant 2

HCID 131422-Butanone, 3-bromo-HCID 988513,5-Dibromo-2-pyridylamine

Product 1

HCID 121060806,8-Dibromo-2,3-dimethylimidazo[1,2-a]pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 31.8 g of 2-amino-3,5-dibromopyridine, 22 g of 3-bromo-2-butanone and 350 ml of tetrahydrofuran is heated at reflux for 9 days and the resulting precipitate is filtered off and dried under reduced pressure. The precipitate is then suspended in 1 l of water, and the suspension is adjusted to pH 8 using 6 M aqueous sodium hydroxide solution. The resulting precipitate is filtered off and washed with water. This gives 28 g of the title compound of m.p. above 90° C. (sinters).

Workup

  1. temperatureis heated
  2. temperatureat reflux for 9 days
  3. filtrationthe resulting precipitate is filtered off
  4. customdried under reduced pressure
  5. filtrationThe resulting precipitate is filtered off
  6. washwashed with water

Sources & evidence

ORD record
ord-1182fd28663149feb698cf89a0066a47
Source dataset
uspto-grants-2007_05
Patent number
US07223771B2

Reaction notes

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