N-Iodosuccinimide → 5-Bromo-3-iodo-1H-pyrrolo(2,3-b)pyridine
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[I:11]N1C(=O)CCC1=O>ClC(Cl)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([I:11])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 95 °C
Procedure
A mixture of 5-Bromo-1H-pyrrolo[2,3-b]pyridine (50 g, 252.5 mmol) and N-iodosuccinimide (13.6 g, 60.6 mmol) in dichloroethane (200 ml) was stirred at 95° C. overnight. The reaction was allowed to cool to room temperature and saturated Na2H2SO4 (200 ml) was added. The mixture was then extracted with ethyl acetate (400 ml×2). The combined organic layers were dried with Na2SO4, concentrated. Silica gel chromatography of the crude using a gradient of ethyl acetate and hexane afforded 5-bromo-3-iodo-1H-pyrrolo[2,3-b]pyridine (62.8 g, 77% yield).
Workup
- temperatureto cool to room temperature
- extractionThe mixture was then extracted with ethyl acetate (400 ml×2)
- dry with materialThe combined organic layers were dried with Na2SO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-41ec2e0ee6144f76977d0f6483d56ef1
- Source dataset
- uspto-grants-2012_08
- Patent number
- US08242280B2
Reaction notes
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