Potassium Hydroxide → HCID 22258169, compound

HRID 1610879Notes

Reaction equation

HRID 1610879 reaction equation
[Br:1][C:2]1[N:6]2[C:7](Cl)=[CH:8][CH:9]=[C:10]([C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[O:12])[C:5]2=[N:4][CH:3]=1.[OH-:20].[K+]>C(O)C>[C:11]([C:10]1[CH:9]=[CH:8][C:7](=[O:20])[N:6]2[C:2]([Br:1])=[CH:3][NH:4][C:5]=12)(=[O:12])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 22258287HCID 22258287, compound

Product 1

HCID 22258169HCID 22258169, compoundYield 4.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

40 mg (0.12 mmol) of 3-bromo-5chloroimidazo[1,2-a]pyridin-8-yl)(phenyl)methanone (example L) are dissolved in 5 ml of potassium hydroxide—solution (10% in water) and 5 ml of ethanol. The mixture is stirred for 24 h at rt. The solvent is evaporated under vacuum and water is added to the crude. The solution is extracted for with ethyl acetate. The collected organic phases are reextracted with brine solution and dried over sodium sulfate. The solvent is evaporated under vacuum and the crude is purified over preparative HPLC (RP18-Column, eluent: acetonitrilewater-gradient) to yield 1.6 mg (4.2% of th.) 8-Benzoyl-3-bromoimidazo[1,2-a]pyridin-5(1H)-one.

Workup

  1. customThe solvent is evaporated under vacuum and water
  2. additionis added to the crude
  3. extractionThe solution is extracted for with ethyl acetate
  4. dry with materialdried over sodium sulfate
  5. customThe solvent is evaporated under vacuum
  6. customthe crude is purified over preparative HPLC (RP18-Column, eluent: acetonitrilewater-gradient)

Sources & evidence

ORD record
ord-260ac36685df41e3966a86263b03f220
Source dataset
uspto-grants-2006_01
Patent number
US06984646B2

Reaction notes

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