Tetrahydrofuran → 5-Bromo-1-(4-fluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13]([CH3:14])=[CH:12][CH:11]=[C:10]([C:15]#[N:16])[C:9]2=[O:17])=[CH:4][CH:3]=1.O1CCCC1.[Br:23]N1C(=O)CCC1=O.C(=O)([O-])O.[Na+]>C(#N)C.C(OCC)(=O)C>[Br:23][C:12]1[CH:11]=[C:10]([C:15]#[N:16])[C:9](=[O:17])[N:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[C:13]=1[CH3:14]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 60 °C
Procedure
To a solution of 1-(4-fluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile (1 g, 4.05 mmol) in acetonitrile (10 mL)/tetrahydrofuran (5 mL) was added N-bromosuccinimide (792 mg, 4.46 mmol), and the mixture was stirred at 60° C. overnight. After cooling to room temperature, saturated aqueous sodium hydrogen carbonate solution and ethyl acetate were added to the reaction mixture, and the mixture was extracted 3 times with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated under reduced pressure. The obtained residue was washed with diethyl ether and collected by filtration to give the title compound (1.07 g, 86%) as a slightly yellow solid.
Workup
- temperatureAfter cooling to room temperature
- extractionthe mixture was extracted 3 times with ethyl acetate
- washThe organic layer was washed with saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- customThe solvent was evaporated under reduced pressure
- washThe obtained residue was washed with diethyl ether
- filtrationcollected by filtration
Sources & evidence
- ORD record
- ord-ebf3ebaf7671419a91cdc7b0b827824e
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08445509B2
Reaction notes
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