Sodium Sulfate → 3-Bromo-6-(difluoromethoxy)-2,4-dimethylpyridine
Reaction equation
[Br:1][C:2]1[C:3]([CH3:10])=[CH:4][C:5]([OH:9])=[N:6][C:7]=1[CH3:8].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>[Br:1][C:2]1[C:7]([CH3:8])=[N:6][C:5]([O:9][CH:15]([F:20])[F:19])=[CH:4][C:3]=1[CH3:10]Participants
6
Procedure
A mixture of 5-bromo-4,6-dimethylpyridin-2-ol obtained in Preparation Example 23(1) (500 mg), 2-(fluorosulfonyl)difluoroacetic acid (0.307 mL) and sodium sulfate (70.3 mg) was stirred in an acetonitrile solvent (10 mL) at room temperature for 3.5 hours. A saturated aqueous sodium bicarbonate solution was added to the reaction mixture, and the mixture was then concentrated under reduced pressure. The residue was extracted with ethyl acetate, and the organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 0% to 10%) to give the title compound (68.6 mg).
Workup
- concentrationthe mixture was then concentrated under reduced pressure
- extractionThe residue was extracted with ethyl acetate
- concentrationthe organic layer was concentrated under reduced pressure
- customThe residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 0% to 10%)
Sources & evidence
- ORD record
- ord-b22ed19fc9b04cefbd85b6c79e17ca0d
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08563565B2
Reaction notes
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