Iodine → N-(3-Iodopyridin-2-yl)-2,2-dimethylpropanamide
Reaction equation
[CH3:1][C:2]([CH3:13])([CH3:12])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)=[O:4].CN(C)CCN(C)C.C([Li])CCC.[I:27]I.S([O-])([O-])(=O)=S.[Na+].[Na+]>O.C1COCC1>[I:27][C:11]1[C:6]([NH:5][C:3](=[O:4])[C:2]([CH3:13])([CH3:12])[CH3:1])=[N:7][CH:8]=[CH:9][CH:10]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a mixture of 2,2-dimethyl-N-pyridin-2-yl-propionamide (3.0 g, 17 mmol) described in Manufacturing Example 1-2-1, N,N,N′,N′-tetramethylethylenediamine (6.3 mL, 42 mmol)), and THF (60 mL) was added n-butyl lithium (1.6 M n-hexane solution, 30 mL) by drops at −78° C., which was stirred overnight at 0° C. Iodine (6.8 g) was added at −78° C. to the reaction mixture, which was stirred for 1.5 hours at 0° C. Water and a saturated aqueous sodium thiosulfate were added to the reaction mixture, which was then extracted with ethyl acetate. The organic layer was washed with saturated brine, and the solvent was evaporated under a reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:heptane=2:1) to obtain the titled compound (2.9 g).
Workup
- stirringwas stirred for 1.5 hours at 0° C
- extractionwas then extracted with ethyl acetate
- washThe organic layer was washed with saturated brine
- customthe solvent was evaporated under a reduced pressure
- customThe residue was purified by silica gel column chromatography (ethyl acetate:heptane=2:1)
Sources & evidence
- ORD record
- ord-e4164981b29c4cd4a58959a02f28e5f5
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08183264B2
Reaction notes
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