Iodine chloride → 2-Chloro-5-iodopyridin-4-amine
Reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][N:3]=1.C([O-])(=O)C.[Na+].[I:14]Cl>C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([NH2:8])[C:5]([I:14])=[CH:4][N:3]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
A 100 mL round bottom flask was charged with 2-chloro-4-amino pyridine (3.0 g, 23.34 mmol), sodium acetate (11.49 g, 140 mmol) and acetic acid (60 mL). To this iodine monochloride (3.98 g, 24.50 mmol) was added and the reaction mixture stirred at 60° C. for 2 h. The reaction was cooled to room temperature and quenched with 1N saturated sodium bis-sulfite solution and extracted with DCM. The organic layer was dried over sodium sulfate and concentrated in vacuo. The crude was purified by silica gel flash chromatography using DCM-MeOH: 95-5. 2-Chloro-5-iodo-pyridin-4-ylamine was obtained as a white color solid. ESI-MS: m/z 255.0 (M+H)+
Workup
- temperatureThe reaction was cooled to room temperature
- customquenched with 1N saturated sodium bis-sulfite solution
- extractionextracted with DCM
- dry with materialThe organic layer was dried over sodium sulfate
- concentrationconcentrated in vacuo
- customThe crude was purified by silica gel flash chromatography
Sources & evidence
- ORD record
- ord-8f6acf60742d4128a7730b703ec04f30
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08383827B2
Reaction notes
Loading…