Water → HCID 117769919, compound

HRID 1526329Notes

Reaction equation

HRID 1526329 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]([C:8]2[C:13]([F:14])=[CH:12][CH:11]=[CH:10][C:9]=2[F:15])[C:4](=[O:16])[C:3]=1[C:17]#[N:18].[Br:19]N1C(=O)CCC1=O.O>CN(C)C=O>[Br:19][C:7]1[C:2]([Cl:1])=[C:3]([C:17]#[N:18])[C:4](=[O:16])[N:5]([C:8]2[C:13]([F:14])=[CH:12][CH:11]=[CH:10][C:9]=2[F:15])[CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 117770649HCID 117770649, compound

Product 1

HCID 117769919HCID 117769919, compoundYield 43.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-chloro-1-(2,6-difluorophenyl)-2-oxo-1,2-dihydropyridine-3-carbonitrile obtained in Step E (670 mg) in N,N-dimethylformamide (5.0 mL) was added N-bromosuccinimide (548 mg) at room temperature. The reaction mixture was heated at 50° C. for 4 hr, and cooled to room temperature. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The extract was washed with water, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (380 mg).

Workup

  1. temperaturecooled to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-847c54bfc22b4a18b4e08e7ed7d982ef
Source dataset
uspto-grants-2015_07
Patent number
US09085578B2

Reaction notes

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