N-bromobutanimide → HCID 136399879, compound

HRID 2388149Notes

Reaction equation

HRID 2388149 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:21])=[C:8]2[C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[N:13][O:12][C:9]2=[CH:10][N:11]=1)=[O:5])[CH3:2].[Br:22]N1C(=O)CCC1=O>C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:21])=[C:8]2[C:14]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[N:13][O:12][C:9]2=[C:10]([Br:22])[N:11]=1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 136399878HCID 136399878, compound

Product 1

HCID 136399879HCID 136399879, compoundYield 86.8%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 4-hydroxy-3-phenyl-isoxazolo[5,4-c]pyridine-5-carboxylic acid ethyl ester (388.1 mg, 1.37 mmol), N-bromosuccinimide (255 mg, 1.43 mmol), benzoyl peroxide (16 mg, 0.07 mmol), and carbon tetrachloride (10 ml) was refluxed for 3 h before it was cooled to room temperature and partitioned between dichloromethane and water. The organic layer was washed with saturated aqueous sodium bicarbonate solution and brine before it was dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel with a gradient of ethyl acetate and dichloromethane to give the title compound as a white solid (432 mg): MS: (−) m/z 361.21, 363.23 (M−1, 79Br/81Br).

Workup

  1. temperaturewas refluxed for 3 h before it
  2. custompartitioned between dichloromethane and water
  3. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution and brine before it
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel with a gradient of ethyl acetate and dichloromethane

Sources & evidence

ORD record
ord-8202f0bf2df443b1a6aa0d395189d215
Source dataset
uspto-grants-2012_09
Patent number
US08269008B2

Reaction notes

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