Phenacyl bromide → HCID 19916794, compound

HRID 1756088Notes

Reaction equation

HRID 1756088 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([CH3:11])=[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[NH:8][C:5]2=[N:6][CH:7]=1.[CH2:18](Br)[C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:20].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.C(O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([CH3:11])=[C:9]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:8]=[C:5]2[N:6]([CH2:18][C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:20])[CH:7]=1

Participants

6

Reactant 3

HCID 6259Phenacyl bromideHCID 10340Sodium CarbonateHCID 22477574HCID 22477574, compound

Product 1

HCID 19916794HCID 19916794, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6342AcetonitrileSolvent

Procedure

5-Bromo-3-methyl-2-phenylpyrrolo[2,3-b]pyridine (0.34 g, 1.2 mmol) and phenacyl bromide (0.49 g, 2.4 mmol) in acetonitrile (20 ml) was refluxed over night to give a clear solution. The cooled solution was alkalized with sodium carbonate solution (10%) and extracted with methylene chloride. Drying over MgSO4, filtration and evaporation of solvents gave a residue which was dissolved in the minimum amount of ethanol. Crystallization was driven to completeness by keeping crystals and mother liquor in the fridge for a few days. Recrystallization by dissolving in hot ethanol and cooling in the fridge over night gave 0.35 g (73%) of yellow crystals.

Workup

  1. customto give a clear solution
  2. extractionextracted with methylene chloride
  3. dry with materialDrying over MgSO4, filtration and evaporation of solvents
  4. customgave a residue which
  5. customCrystallization
  6. customfor a few days
  7. customRecrystallization
  8. dissolutionby dissolving in hot ethanol
  9. temperaturecooling in the fridge over night

Sources & evidence

ORD record
ord-0fe7a6b7551c4710b6f0037f4acf2272
Source dataset
uspto-grants-1995_08
Patent number
US05439917

Reaction notes

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