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

HRID 422409Notes

Reaction equation

HRID 422409 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-7d116d6fd1f64d7b99116a8f4f8c7ef9
Source dataset
uspto-grants-2012_01
Patent number
US08101637B2

Reaction notes

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