Water → HCID 117770289, compound

HRID 1526315Notes

Reaction equation

HRID 1526315 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]([CH:8]([CH:10]([CH3:12])[CH3:11])[CH3:9])[C:4](=[O:13])[C:3]=1[C:14]#[N:15].[Br:16]N1C(=O)CCC1=O.O>CN(C)C=O>[Br:16][C:7]1[C:2]([Cl:1])=[C:3]([C:14]#[N:15])[C:4](=[O:13])[N:5]([CH:8]([CH:10]([CH3:11])[CH3:12])[CH3:9])[CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 117770690HCID 117770690, compound

Product 1

HCID 117770289HCID 117770289, compoundYield 93.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-chloro-1-(3-methylbutan-2-yl)-2-oxo-1,2-dihydropyridine-3-carbonitrile obtained in Step E (305 mg) in N,N-dimethylformamide (3.0 mL) was added N-bromosuccinimide (296 mg) at room temperature. The reaction mixture was heated at 50° C. for 4 hr, and cooled to room temperature. The reaction mixture was poured into 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 (386 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-b8cfd5b19c584ddb87a4f8ab1802f6e9
Source dataset
uspto-grants-2015_07
Patent number
US09085578B2

Reaction notes

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