N-Iodosuccinimide → Methyl 3-iodo-1H-pyrrolo[2,3-b]pyridine-5-carboxylate

HRID 2089042Notes

Reaction equation

HRID 2089042 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

HCID 120273N-IodosuccinimideHCID 22832049methyl 1H-pyrrolo[2,3-b]pyridine-5-carboxylate

Product 1

HCID 24229255Methyl 3-iodo-1H-pyrrolo[2,3-b]pyridine-5-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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

  1. customThe solvent was evaporated
  2. filtrationfiltered
  3. customThe collected solid was triturated with dichloromethane
  4. filtrationthe mixture filtered
  5. concentrationThe dichloromethane filtrate was concentrated to a brown powder that
  6. 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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