Water → HCID 131735960, compound

HRID 2207932Notes

Reaction equation

HRID 2207932 reaction equation
[Na+].[Br:2][C:3]1[N:8]=[CH:7][C:6]([CH:9]=[CH:10][C:11](=[O:15])[C:12]([O-:14])=[O:13])=[CH:5][CH:4]=1.[CH3:16]I.O>CN(C)C=O>[CH3:16][O:13][C:12](=[O:14])[C:11](=[O:15])[CH:10]=[CH:9][C:6]1[CH:7]=[N:8][C:3]([Br:2])=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6328Methyl iodideHCID 118432169HCID 118432169, compound

Product 1

HCID 131735960HCID 131735960, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of the 4-(6-bromo-pyridin-3-yl)-2-oxo-3-butenoic acid sodium salt (900.0 mg, 3.2 mmol) in the form of a pale yellow solid, methyl iodide (400.0 mL, 6.47 mmol) in N,N-dimethylformamide (20.0 mL) was stirred at 75° C. for 3 hours. Distilled water was added to the reaction mixture, which was then extracted with ethyl acetate. The extract was washed with a saturated solution of sodium hydrogen carbonate and brine, dried on anhydrous magnesium sulfate, and then concentrated under reduced pressure to give 615.0 mg of the titled compound as a pale yellow solid.

Workup

  1. extractionwas then extracted with ethyl acetate
  2. washThe extract was washed with a saturated solution of sodium hydrogen carbonate and brine
  3. dry with materialdried on anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-14328e3d32d44bc99982171c153513f7
Source dataset
uspto-grants-2016_06
Patent number
US09376420B2

Reaction notes

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