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

HRID 1675959Notes

Reaction equation

HRID 1675959 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 (11-2, 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 (11-3) 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-b039488a5e414f4289ddd53f27b5fb2b
Source dataset
uspto-grants-2011_08
Patent number
US08003797B2

Reaction notes

Loading…