Iodine → N-(4-Iodo-6-methoxy-3-pyridinyl)-2,2-dimethylpropanamide
Reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([NH:9][C:10](=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:5][CH:4]=1.[Li]C(C)(C)C.[I:21]I>C1COCC1>[I:21][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[N:8]=[CH:7][C:6]=1[NH:9][C:10](=[O:15])[C:11]([CH3:12])([CH3:14])[CH3:13]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a solution of N-(6-methoxypyridin-3-yl)pivalamide (Compound 1, 7.4 g, 35.6 mmol) in anhydrous THF (200 ml) at −78° C. under argon was added t-BuLi (1.7 M in pentane, 52 ml, 89.0 mmol) slowly. After stirred at −78° C. for 1 h, a solution of I2 (22.6 g, 89.0 mmol) in anhydrous THF (100 ml) at −78° C. was cannulated into the reaction over 20 min and the reaction was stirred for 15 min at −78° C. The cooling bath was then removed and the reaction stirred for 30 min, quenched cautiously with ice, extracted with CH2Cl2. The organic layer was 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.
Workup
- stirringthe reaction was stirred for 15 min at −78° C
- customThe cooling bath was then removed
- stirringthe reaction stirred for 30 min
- customquenched cautiously with ice
- extractionextracted with CH2Cl2
- dry with materialThe organic layer was dried over Na2SO4
- concentrationconcentrated in vacuo
- customThe residue was purified by chromatography on silica gel (0→30% EtOAc-hexanes)
Sources & evidence
- ORD record
- ord-fa494021de364114be4544eef00f9fc6
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08536339B2
Reaction notes
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