Sodium hydride → 2-bromo-5-(((1R)-2,2-difluorocyclopropyl)methoxy)-4-methylpyridine
Reaction equation
[Br:1][C:2]1[N:7]=[CH:6][C:5]([OH:8])=[C:4]([CH3:9])[CH:3]=1.[N+](C1C=CC(S(O[CH2:23][C@H:24]2[CH2:26][C:25]2([F:28])[F:27])(=O)=O)=CC=1)([O-])=O.[H-].[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH3:9])[C:5]([O:8][CH2:23][C@H:24]2[CH2:26][C:25]2([F:28])[F:27])=[CH:6][N:7]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 6-bromo-4-methylpyridin-3-ol (0.50 g) and ((1R)-2,2-difluorocyclopropyl)methyl 4-nitrobenzenesulfonate (1.077 g) in DMF (50 mL) was added sodium hydride (60% in oil, 0.106 g) under ice-cooling, and the mixture was stirred for 15 hr. The reaction mixture was concentrated under reduced pressure. The residue was diluted with ethyl acetate, and the mixture was washed with saturated brine. The obtained organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (0.35 g).
Workup
- temperaturecooling
- concentrationThe reaction mixture was concentrated under reduced pressure
- additionThe residue was diluted with ethyl acetate
- washthe mixture was washed with saturated brine
- dry with materialThe obtained organic layer was dried over anhydrous magnesium sulfate
- customthe solvent was evaporated under reduced pressure
- customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)
Sources & evidence
- ORD record
- ord-57268d9c5ffe4851b0bef064efcab577
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09133129B2
Reaction notes
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