Water → 2-(3-Oxo-[1,2,4]triazolo[4,3-a]pyridin-2-ylmethyl)acrylic acid methyl ester
Reaction equation
[N:1]1[NH:2][C:3](=[O:10])[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.[H-].[Na+].Br[CH2:14][CH:15]([CH2:20]Br)[C:16]([O:18][CH3:19])=[O:17].O>CN(C)C=O.C(OCC)(=O)C>[CH3:19][O:18][C:16](=[O:17])[C:15]([CH2:20][N:2]1[C:3](=[O:10])[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]2=[N:1]1)=[CH2:14]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
After dissolving 2H-[1,2,4]triazolo[4,3-a]pyridin-3-one (CAS 6969-71-7) (1.0 g) in N,N-dimethylformamide (50 ml), sodium hydride (60% in oil) (355 mg) was added while stirring on ice. After stirring for 20 minutes, methyl 3-bromo-2-(bromomethyl)propionate (2.11 ml) was added dropwise. Stirring was continued for 1 hour and 30 minutes, and then sodium hydride (60% in oil) (200 mg) was added and the mixture was stirred for 3 hours. Water was added to the reaction mixture, and extraction was performed with ethyl acetate. The organic layer was washed with water and brine in that order and then dried over anhydrous magnesium sulfate. After filtration, the solvent was distilled off under reduced pressure. The residue was purified by NH silica gel column chromatography to obtain the title compound (400 mg).
Workup
- additionwas added
- stirringAfter stirring for 20 minutes
- stirringStirring
- stirringthe mixture was stirred for 3 hours
- washThe organic layer was washed with water and brine in that order
- dry with materialdried over anhydrous magnesium sulfate
- filtrationAfter filtration
- distillationthe solvent was distilled off under reduced pressure
- customThe residue was purified by NH silica gel column chromatography
Sources & evidence
- ORD record
- ord-27aa4b6cbe6a4901ad71e4490bbf1562
- Source dataset
- uspto-grants-2012_08
- Patent number
- US08252810B2
Reaction notes
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