Methyl iodide → 6-bromo-N-methylpyridin-2-amine

HRID 334689Notes

Reaction equation

HRID 334689 reaction equation
[H-].[Na+].[Br:3][C:4]1[N:9]=[C:8]([NH2:10])[CH:7]=[CH:6][CH:5]=1.I[CH3:12]>CN(C=O)C>[Br:3][C:4]1[N:9]=[C:8]([NH:10][CH3:12])[CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 3008092-Amino-6-bromopyridine

Product 1

HCID 134703156-bromo-N-methylpyridin-2-amineYield 28%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH (150 mg, 3.80 mmol, 60%) was added to a solution of 6-bromo-pyridin-2-ylamine (300 mg, 1.73 mmol) in DMF at 0° C. followed by iodomethane (3.47 mL, 6.94 mmol). The reaction mixture was stirred for 1 hour at room temperature and was quenched with water. The aqueous phase was extracted with Et2O. The organic phase was washed with water, brine, dried over MgSO4, filtered and evaporated. The crude residue was purified by flash chromatography (cyclohexane/AcOEt 95:5) to yield 90 mg (0.48 mmol, 28%) of (6-bromo-pyridin-2-yl)-methyl-amine.

Workup

  1. customwas quenched with water
  2. extractionThe aqueous phase was extracted with Et2O
  3. washThe organic phase was washed with water, brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude residue was purified by flash chromatography (cyclohexane/AcOEt 95:5)

Sources & evidence

ORD record
ord-4553ef4105254d188d5e47b5b4eb4f46
Source dataset
uspto-grants-2014_11
Patent number
US08883826B2

Reaction notes

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