Sodium Methoxide → 6-Iodo-2,3-dimethoxypyridine

HRID 1675960Notes

Reaction equation

HRID 1675960 reaction equation
Br[C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[C:4]([I:10])[N:3]=1.[CH3:11][O-:12].[Na+]>CN(C=O)C>[CH3:11][O:12][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[C:4]([I:10])[N:3]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 110990402-Bromo-6-iodo-3-methoxypyridine

Product 1

HCID 453617466-Iodo-2,3-dimethoxypyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-bromo-3-methoxy-6-iodopyridine (11-3, 34 g, 162 mmol) in DMF (65 mL) was added sodium methoxide (37 mL, 162 mmol) and heated to 100° C. The mixture was stirred for 10 minutes and partitioned between saturated NaHCO3 and DCM. The organic phase was washed with brine, dried over Na2SO4, filtered and concentrated. The crude material was purified by gradient elution on silica (0 to 20% EtOAc in hexanes) to afford the title compound (11-4) as a white powder. ESI+MS [M+H]+ C7H8INO2: 265.8 found, 266.0 required

Workup

  1. custompartitioned between saturated NaHCO3 and DCM
  2. washThe organic phase was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified by gradient elution on silica (0 to 20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-f3625607048842e0a661da2d5d3cd9bb
Source dataset
uspto-grants-2011_08
Patent number
US08003797B2

Reaction notes

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