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

HRID 1948577Notes

Reaction equation

HRID 1948577 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 (7-3, 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 (7-4) 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-c7c292ccbd1642a892f0c049e9d8f582
Source dataset
uspto-grants-2013_03
Patent number
US08399494B2

Reaction notes

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