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

HRID 1802344Notes

Reaction equation

HRID 1802344 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.[K+].[K+].CI.O>CN(C=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

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 109794792-Bromo-6-iodopyridin-3-ol

Product 1

HCID 110990402-Bromo-6-iodo-3-methoxypyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-bromo-3-hydroxy-6-iodopyridine (5-2, 40 g, 133 mmol) in DMF (80 ml) was added K2CO3 (16.77 g, 121 mmol) and methyl iodide (66.3 g, 467 mmol). The system was stirred for 45 minutes at 100° C., cooled to room temperature and then treated with water (650 mL) and stirred for 0.5 h. The resulting solids that precipitated from solution were isolated by filtration and dried to give the title compound (5-3) as a pale brown solid. ESI+MS C6H5BrINO: 313.8 found, 313.9 required.

Workup

  1. temperaturecooled to room temperature
  2. stirringstirred for 0.5 h
  3. customThe resulting solids that precipitated from solution
  4. customwere isolated by filtration
  5. customdried

Sources & evidence

ORD record
ord-049a14be832744d5b9956e4880309ab5
Source dataset
uspto-grants-2013_01
Patent number
US08349872B2

Reaction notes

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