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

HRID 606004Notes

Reaction equation

HRID 606004 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=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.O>[Br:18][C:15]1[CH:16]=[CH:17][C:12]2[N:13]([CH:2]=[C:3]([C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:11]=2)[CH:14]=1

Participants

6

Reactant 3

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

Product 1

HCID 6234306-Bromo-2-phenylimidazo[1,2-a]pyridineYield 65.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
80 °C

Procedure

1.99 g of 2-bromo-1-phenylethanone, 1.73 g of 2-amino-5-bromopyridine and 1 g of sodium hydrogen carbonate in a mixture of 20 ml of ethanol and 5 ml of water are placed in a round-bottomed flask. The mixture is heated at 80° C. for 4 h and left to cool and 40 ml of water are added. The mixture is stirred for 15 min and the precipitate is then recovered by filtration; it is washed with water and then with diisopropyl ether and dried in a desiccator. 1.8 g of compound are obtained. Mp=192-194° C.

Workup

  1. customare placed in a round-bottomed flask
  2. waitleft
  3. temperatureto cool
  4. filtrationthe precipitate is then recovered by filtration
  5. washit is washed with water
  6. dry with materialwith diisopropyl ether and dried in a desiccator

Sources & evidence

ORD record
ord-2bcb30a127054ab8a05e88ed9150b6aa
Source dataset
uspto-grants-2011_03
Patent number
US07915284B2

Reaction notes

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