Methyl iodide → HCID 68705964, compound

HRID 1809603Notes

Reaction equation

HRID 1809603 reaction equation
[N:1]1[CH:6]=[C:5]([OH:7])[CH:4]=[CH:3][C:2]=1[OH:8].[H-].[Na+].[Br:11][C:12]1[CH:13]=[C:14]([N+]([O-])=O)[C:15]([C:18]#[N:19])=[N:16][CH:17]=1.[CH3:23]I>CN(C)C=O.O>[Br:11][C:12]1[CH:13]=[C:14]([O:7][C:5]2[CH:4]=[CH:3][C:2](=[O:8])[N:1]([CH3:23])[CH:6]=2)[C:15]([C:18]#[N:19])=[N:16][CH:17]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydride2×HCID 27696985-Bromo-3-nitropyridine-2-carbonitrileHCID 178516290HCID 178516290, compound

Product 1

HCID 68705964HCID 68705964, compoundYield 54.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of pyridine-2,5-diol (1.0 g, 9.0 mmol) in dimethylformamide (150 mL) at 0° C. was added sodium hydride (60% dispersion in mineral oil, 0.30 g, 9.0 mmol) in portions, and the reaction stirred at 0° C. for 1 hour. To this reaction was added 5-bromo-3-nitropicolinonitrile (2.05 g, 9.00 mmol) and the reaction stirred overnight at ambient temperature. Sodium hydride (60% dispersion in mineral oil, 0.30 g, 9.0 mmol) was added to the reaction mixture in portions, followed by methyl iodide (2.56 g, 18.00 mmol), and the reaction was stirred at ambient temperature for 3 hours. The reaction was poured into water and the aqueous layer extracted with ethyl acetate. The organics were washed with 1N HCl, 1M NaOH, water, brine, dried over magnesium sulfate and concentrated in vacuo. The material purified over silica gel (2% ethyl acetate/dichloromethane) to afford 5-bromo-3-(1-methyl-6-oxo-1,6-dihydropyridin-3-yloxy)picolinonitrile (1.5 g, 54%).

Workup

  1. stirringthe reaction stirred overnight at ambient temperature
  2. stirringthe reaction was stirred at ambient temperature for 3 hours
  3. extractionthe aqueous layer extracted with ethyl acetate
  4. washThe organics were washed with 1N HCl, 1M NaOH, water, brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe material purified over silica gel (2% ethyl acetate/dichloromethane)

Sources & evidence

ORD record
ord-c2e8453f6791497db87d4dd0b9e8d941
Source dataset
uspto-grants-2013_01
Patent number
US08362037B2

Reaction notes

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