Iodine → tert-Butyl (4-chloro-3-iodopyridin-2-yl)carbamate
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:3]=1.CN(CCN(C)C)C.[Li]CCCC.[I:29]I.[NH4+].[Cl-]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])[C:3]=1[I:29]Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a solution tert-butyl 4-chloropyridin-2-ylcarbamate (2.29 g, 10 mmol), TMEDA (2.32 g, 20 mmol) in anhydrous THF (30 mL) was added n-BuLi (8 ml, 20 mmol). The resulting mixture was allowed to stir at −78° C. for 0.5 h which was added the solution of I2 (2.54 g, 10 mmol) in THF (8 mL) dropwise at −78° C. The reaction mixture was stirred for another 4 h. To the solution was added NH4Cl aq (5 mL), extracted with EtOAc (3×20 mL), dried over Na2SO4, filtered and concentrated. The crude residue was purified by column chromatography to afford the title compound as a yellow solid. LC/MS m/z=355.19 [M+H]+
Workup
- stirringThe reaction mixture was stirred for another 4 h
- extractionextracted with EtOAc (3×20 mL)
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customThe crude residue was purified by column chromatography
Sources & evidence
- ORD record
- ord-8c646788ac8f46708e34e70700143ef5
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09273033B2
Reaction notes
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