N-Iodosuccinimide → 7-Fluoro-3-iodo-1H-pyrrolo[3,2-c]pyridine

HRID 1753065Notes

Reaction equation

HRID 1753065 reaction equation
[F:1][C:2]1[C:3]2[NH:10][CH:9]=[CH:8][C:4]=2[CH:5]=[N:6][CH:7]=1.C1C(=O)N([I:18])C(=O)C1>CN(C=O)C.O.CCOC(C)=O>[F:1][C:2]1[C:3]2[NH:10][CH:9]=[C:8]([I:18])[C:4]=2[CH:5]=[N:6][CH:7]=1

Participants

6

Reactant 2

HCID 120273N-IodosuccinimideHCID 53413168HCID 53413168, compound

Product 1

HCID 534131647-Fluoro-3-iodo-1H-pyrrolo[3,2-c]pyridineYield 51.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 7-fluoro-pyrrolo[3,2-c]pyridine (Preparation 62, 5 g, 36.76 mmol) in anhydrous DMF (35 mL) was added NIS (9 g, 40.44 mmol), and the reaction stirred at room temperature for 4 hours. The reaction was diluted with water and EtOAc. The organic layer was collected, washed with saturate aqueous NaHCO3 solution, brine, dried over sodium sulphate and concentrated in vacuo. The residue was purified using silica gel column chromatography eluting with 50-100% EtOAc in heptanes followed by 5% MeOH in DCM to afford the title compound (5 g).

Workup

  1. customThe organic layer was collected
  2. washwashed with saturate aqueous NaHCO3 solution, brine
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified
  6. washeluting with 50-100% EtOAc in heptanes

Sources & evidence

ORD record
ord-f91460d82cc848d89c95fbe52c2bc669
Source dataset
uspto-grants-2015_10
Patent number
US09163021B2

Reaction notes

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