Trifluoroacetic anhydride → 2-(2-Fluoro-5-methoxyphenyl)-3-isobutoxy-5-(methoxycarbonyl)pyridine 1-oxide
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[C:19]([O:20][CH2:21][CH:22]([CH3:24])[CH3:23])=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][N:11]=1.NC(N)=[O:27].OO.FC(F)(F)C(OC(=O)C(F)(F)F)=O.C(=O)([O-])O.[Na+]>C(#N)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[C:19]([O:20][CH2:21][CH:22]([CH3:24])[CH3:23])=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][N+:11]=1[O-:27]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Under a nitrogen atmosphere, to a solution of methyl 6-(2-fluoro-5-methoxyphenyl)-5-isobutoxynicotinate (758 mg) in acetonitrile (9.4 mL) were added urea-hydrogen peroxide adduct (555 mg) and trifluoroacetic anhydride (793 μL) at 0° C., and the mixture was gradually warmed to room temperature and stirred overnight. Saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, and the solvent was evaporated under reduced pressure. The residue was filtered, and the solvent in the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (631 mg) as a pale-yellow oil.
Workup
- customthe solvent was evaporated under reduced pressure
- filtrationThe residue was filtered
- customthe solvent in the filtrate was evaporated under reduced pressure
- customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)
Sources & evidence
- ORD record
- ord-f149ca36eb9b4e2f85a9af4bd5e3dfc5
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09181186B2
Reaction notes
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