Water → 2-Bromo-6-iodo-3-methoxypyridine

HRID 604213

Reaction equation

HRID 604213 reaction equation
[Br:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([I:9])[N:3]=1.[C:10](=O)([O-])[O-].[Cs+].[Cs+].CI.O>CN(C)C=O.C(OCC)(=O)C>[Br:1][C:2]1[C:7]([O:8][CH3:10])=[CH:6][CH:5]=[C:4]([I:9])[N:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 109794792-Bromo-6-iodopyridin-3-ol

Product 1

HCID 110990402-Bromo-6-iodo-3-methoxypyridineYield 78.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Bromo-6-iodo-pyridin-3-ol (2.98 g) is dissolved in N,N-dimethylformamide (140 ml) and thereto are added cesium carbonate (16.3 g) and methyl iodide (1.25 mL) and the mixture is stirred at room temperature overnight. To the reaction solution are added water and ethyl acetate, and the mixture is separated, and the organic layer is washed with a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=19:1→4:1) to give 2-bromo-6-iodo-3-methoxy-pyridine (2.45 g). MS (m/z): 314/316 [M+H]+

Workup

  1. customthe mixture is separated
  2. washthe organic layer is washed with a saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=19:1→4:1)

Sources & evidence

ORD record
ord-f29a74ca54a14148937e15707662d584
Source dataset
uspto-grants-2011_03
Patent number
US07906517B2

Linked notes

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