Potassium Iodide → HCID 117770038, compound

HRID 1526376Notes

Reaction equation

HRID 1526376 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][NH:6][C:5](=[O:9])[C:4]=1[C:10]#[N:11].C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+].Br[CH:21]([CH2:23][CH3:24])[CH3:22]>C(=O)([O-])O.[Na+].COCCOC>[CH:21]([N:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[C:4]([C:10]#[N:11])[C:5]1=[O:9])([CH2:23][CH3:24])[CH3:22]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 65542-BromobutaneHCID 10796Cesium carbonateHCID 27867023-Pyridinecarbonitrile, 1,2-dihydro-4-methoxy-2-oxo-

Product 1

HCID 117770038HCID 117770038, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 4-methoxy-2-oxo-1,2-dihydropyridine-3-carbonitrile (500 mg), cesium carbonate (2.17 g), potassium iodide (553 mg) N,N-dimethylformamide (10 mL) and 1,2-dimethoxyethane (10 mL) was added 2-bromobutane (776 mg) at room temperature, and the mixture was stirred overnight at 60° C. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted threetimes with ethyl acetate. The extracts were combined, 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 (330 mg).

Workup

  1. extractionthe mixture was extracted threetimes with ethyl acetate
  2. washwashed 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-9d34407f90f241f1a9266b80a887fca7
Source dataset
uspto-grants-2015_07
Patent number
US09085578B2

Reaction notes

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