Hydrogen Peroxide → 2-(6-Bromopyridin-2-yl)-2-methylpropanamide
Reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8]([CH3:12])([CH3:11])[C:9]#[N:10])[CH:5]=[CH:4][CH:3]=1.OO.C(=O)([O-])[O-:16].[K+].[K+]>CS(C)=O>[Br:1][C:2]1[N:7]=[C:6]([C:8]([CH3:12])([CH3:11])[C:9]([NH2:10])=[O:16])[CH:5]=[CH:4][CH:3]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
To a solution of 2-(6-bromopyridin-2-yl)-2-methylpropanenitrile (Example 367, Step 1) (200 mg, 0.89 mmol) in dimethylsulfoxide (4 mL) was added hydrogen peroxide (0.42 mL, 4.8 mmol) and potassium carbonate (1.23 g, 8.89 mmol). The reaction was then stirred overnight at 70° C. The resulting slurry was cooled to ambient temperature, filtered and directly purified by reverse phase HPLC (10-100% acteonitrile/water+0.05% TFA modifier) to yield the title compound.
Workup
- temperatureThe resulting slurry was cooled to ambient temperature
- filtrationfiltered
- customdirectly purified by reverse phase HPLC (10-100% acteonitrile/water+0.05% TFA modifier)
Sources & evidence
- ORD record
- ord-78b45d5989f648298460c2852aeefe9f
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08367706B2
Reaction notes
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