Sodium Sulfate → 2-(Difluoromethoxy)-4-iodo-3,5-dimethylpyridine

HRID 1043925Notes

Reaction equation

HRID 1043925 reaction equation
[I:1][C:2]1[C:7]([CH3:8])=[CH:6][N:5]=[C:4]([OH:9])[C:3]=1[CH3:10].FS([C:15]([F:20])([F:19])C(O)=O)(=O)=O.S([O-])([O-])(=O)=O.[Na+].[Na+].C(=O)(O)[O-].[Na+]>C(#N)C>[F:19][CH:15]([F:20])[O:9][C:4]1[C:3]([CH3:10])=[C:2]([I:1])[C:7]([CH3:8])=[CH:6][N:5]=1

Participants

6

Reactant 4

HCID 24436Sodium SulfateHCID 516892Sodium BicarbonateHCID 27375162,2-Difluoro-2-(fluorosulfonyl)acetic acidHCID 178430689HCID 178430689, compound

Product 1

HCID 866863482-(Difluoromethoxy)-4-iodo-3,5-dimethylpyridine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-iodo-3,5-dimethylpyridin-2-ol (350 mg), 2-(fluorosulfonyl)difluoroacetic acid (0.17 mL), and sodium sulfate (39.9 mg) were added to acetonitrile (5.7 mL). The mixture was stirred at room temperature for 3.5 hours. A saturated aqueous sodium bicarbonate solution was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was concentrated under reduced pressure to give the title compound (378.6 mg).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-0e4a0e757bd349caa303e4b7767e4772
Source dataset
uspto-grants-2013_10
Patent number
US08563565B2

Reaction notes

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