N-Iodosuccinimide → 4-Chloro-5-fluoro-3-iodo-1H-pyrrolo[2,3-b]pyridine

HRID 1522021Notes

Reaction equation

HRID 1522021 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][N:5]=[C:4]2[NH:9][CH:10]=[CH:11][C:3]=12.[I:12]N1C(=O)CCC1=O>CN(C)C=O>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][N:5]=[C:4]2[NH:9][CH:10]=[C:11]([I:12])[C:3]=12

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 497616114-Chloro-5-fluoro-1H-pyrrolo(2,3-b)pyridine

Product 1

HCID 497616274-Chloro-5-fluoro-3-iodo-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-chloro-5-fluoro-1H-pyrrolo[2,3-b]pyridine (1.8 g, 10.5 mmol) in N,N-dimethylformamide (25 mL) at 0° C. was added N-iodosuccinimide (2.37 g, 10.55 mmol). The mixture was slowly brought to room temperature, quenched with brine and extracted with ethyl acetate (twice). The organic phase was concentrated and purified by column chromatography (silica gel, 30% ethyl acetate in hexane) to afford the title compound. MS (ESI+) m/z 297 (M+H)+.

Workup

  1. customwas slowly brought to room temperature
  2. customquenched with brine
  3. extractionextracted with ethyl acetate (twice)
  4. concentrationThe organic phase was concentrated
  5. custompurified by column chromatography (silica gel, 30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-079cd6b40ffa4f1a8cab8042b6f6ecc9
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

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