N-bromobutanimide → HCID 118598927, compound

HRID 1050366Notes

Reaction equation

HRID 1050366 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]([O:11][CH3:12])=[O:10])[NH:5][C:6](=[O:8])[CH:7]=1.[Br:13]N1C(=O)CCC1=O.S(=O)(O)[O-].[Na+]>C(#N)C>[Br:13][C:7]1[C:6](=[O:8])[NH:5][C:4]([C:9]([O:11][CH3:12])=[O:10])=[CH:3][C:2]=1[F:1]

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 23665763Sodium BisulfiteHCID 118599022HCID 118599022, compound

Product 1

HCID 118598927HCID 118598927, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of methyl 4-fluoro-6-oxo-1,6-dihydropyridine-2-carboxylate (4, 1 g, 5.84 mmol) in acetonitrile (25 mL) is added N-bromosuccinimide (1.56 g, 8.76 mmol). The reaction is stirred at reflux for 2 h. The resulting mixture is pour into half saturated aqueous sodium bisulfite and extracted with ethyl acetate. The organic layers are combined, dried over magnesium sulfate, filtered and concentrated. The crude is purified via flash chromatography to afford methyl 5-bromo-4-fluoro-6-oxo-1,6-dihydropyridine-2-carboxylate (5).

Workup

  1. temperatureat reflux for 2 h
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude is purified via flash chromatography

Sources & evidence

ORD record
ord-ba46dfc51b804d029af8e6aa0e67d4bb
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

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