Reaction equation
[I:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[N:5]=[CH:4][C:3]=1[NH:10]C(=O)C(C)(C)C>OS(O)(=O)=O>[I:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[N:5]=[CH:4][C:3]=1[NH2:10]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 120 °C
Procedure
A solution of N-(4-iodo-6-methoxypyridin-3-yl)pivalamide (Compound 2, 2.33 g, 7.0 mmol) in 10% H2SO4 (70 ml) was heated to reflux at 120° C. for 5 h. The mixture was cooled to 0° C. and was quenched cautiously with solid NaOH (10 g), extracted with EtOAc (×2). The combined organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by chromatography on silica gel (0→30% EtOAc-hexanes) to yield the title compound as off-white solid.
Workup
- temperatureThe mixture was cooled to 0° C.
- customwas quenched cautiously with solid NaOH (10 g)
- extractionextracted with EtOAc (×2)
- washThe combined organic layer was washed with brine
- dry with materialdried over Na2SO4
- concentrationconcentrated in vacuo
- customThe residue was purified by chromatography on silica gel (0→30% EtOAc-hexanes)
Sources & evidence
- ORD record
- ord-d7d210f18fdd4139a8e5c53277b5f0e8
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08012992B2
Linked notes
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