Sodium Methoxide → 6-Iodo-2,3-dimethoxypyridine
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]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
To a solution of 2-bromo-3-methoxy-6-iodopyridine (5-3, 34 g, 108 mmol) in DMF (65 mL) was added sodium methoxide (37 mL, 162 mmol, 4.37 M in methanol) 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 (5-4) as a white powder. ESI+MS [M+H]+ C7H8INO2: 265.8 found, 266.0 required.
Workup
- custompartitioned between saturated NaHCO3 and DCM
- washThe organic phase was washed with brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customThe crude material was purified by gradient elution on silica (0 to 20% EtOAc in hexanes)
Sources & evidence
- ORD record
- ord-b7e52298e75c4d53a0d6f8286a17946b
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08349872B2
Reaction notes
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