N-Iodosuccinimide → methyl 3-iodo-1H-pyrrolo[2,3-b]pyridine-5-carboxylate
Reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[CH:13]=[CH:12][NH:11][C:8]2=[N:9][CH:10]=1)=[O:4].[I:14]N1C(=O)CCC1=O>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:13]([I:14])=[CH:12][NH:11][C:8]2=[N:9][CH:10]=1)=[O:4]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of Example 235a (1.04 g, 5.9 mmol) in 12 mL anhydrous DMF was added N-iodosuccinimide (1.46 g, 6.49 mmol) and the solution stirred at room temperature for 16 hours. The solvent was evaporated and the residue suspended in water and filtered. The collected solid was triturated with dichloromethane and the mixture filtered. The dichloromethane filtrate was concentrated to a brown powder that was carried on without purification.
Workup
- customThe solvent was evaporated
- filtrationfiltered
- customThe collected solid was triturated with dichloromethane
- filtrationthe mixture filtered
- concentrationThe dichloromethane filtrate was concentrated to a brown powder that
- customwas carried on without purification
Sources & evidence
- ORD record
- ord-88e56c279d2b41248560f24fea579364
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08435980B2
Reaction notes
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