Water → HCID 117770351, compound

HRID 1526362Notes

Reaction equation

HRID 1526362 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[C:15]#[N:16])[C:4](=[O:17])[C:3]=1[C:18]#[N:19].[Br:20]N1C(=O)CCC1=O.O>CN(C)C=O>[Br:20][C:7]1[C:2]([Cl:1])=[C:3]([C:18]#[N:19])[C:4](=[O:17])[N:5]([C:8]2[C:13]([F:14])=[CH:12][CH:11]=[CH:10][C:9]=2[C:15]#[N:16])[CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 117770720HCID 117770720, compound

Product 1

HCID 117770351HCID 117770351, compoundYield 21.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-chloro-1-(2-cyano-6-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carbonitrile obtained in Step E (4.0 g) in N,N-dimethylformamide (40 mL) was added N-bromosuccinimide (3.90 g) at room temperature. The reaction mixture was heated at 50° C. for 16 hr. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium 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 (1.10 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c0965ec4efee49a5866c983efa7a0bd3
Source dataset
uspto-grants-2015_07
Patent number
US09085578B2

Reaction notes

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