Methyl iodide → 5-Bromo-N,N-dimethylpyridine-3-carboxamide

HRID 2406687Notes

Reaction equation

HRID 2406687 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[N:6][CH:7]=[C:8]([CH:13]=1)[C:9]([NH:11][CH3:12])=[O:10].[CH3:14]I.[Cl-].[NH4+]>C(OCC)(=O)C.CN(C=O)C>[Br:3][C:4]1[CH:5]=[N:6][CH:7]=[C:8]([CH:13]=1)[C:9]([N:11]([CH3:14])[CH3:12])=[O:10]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 220497755-Bromo-N-methylpyridine-3-carboxamide

Product 1

HCID 234370495-Bromo-N,N-dimethylpyridine-3-carboxamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
45 °C

Procedure

Sodium hydride (60% in oil) (28 mg) was added to a DMF (2.4 ml) solution containing 5-bromo-N-methylnicotinamide (100 mg), followed by stirring at 45° C. for 1 hour. Methyl iodide (43 μl) was added under ice cooling, followed by stirring at room temperature for 1 hour. A saturated aqueous ammonium chloride solution and ethyl acetate were added to the reaction mixture. The organic layer was collected, washed with saturated saline, and dried over anhydrous magnesium sulfate. The solvent was distilled away under reduced pressure. Hexane was added to the obtained residue, solid matter was collected by filtration, and a white solid of 5-bromo-N,N-dimethylnicotinamide (42 mg) was thus obtained.

Workup

  1. stirringby stirring at room temperature for 1 hour
  2. customThe organic layer was collected
  3. washwashed with saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled away under reduced pressure
  6. additionHexane was added to the obtained residue, solid matter
  7. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-87cf5652e6c3486dbd96f53b70909753
Source dataset
uspto-grants-2014_08
Patent number
US08809371B2

Reaction notes

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