Iodine → 6-fluoro-3-iodo-1H-indole

HRID 1692888Notes

Reaction equation

HRID 1692888 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[OH-].[K+].[I:13]I>CN(C=O)C.C(=O)(O)[O-].[Na+]>[I:13][C:6]1[C:5]2[C:9](=[CH:10][C:2]([F:1])=[CH:3][CH:4]=2)[NH:8][CH:7]=1

Participants

6

Reactant 3

HCID 807IodineHCID 14797Potassium HydroxideHCID 3512786-Fluoroindole

Product 1

HCID 177588846-fluoro-3-iodo-1H-indoleYield 65.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 6-fluoroindole (1.14 g, 8.44 mmol) in DMF (20 mL) was added potassium hydroxide (0.521 g, 9.28 mmol) at 0° C. The resulting mixture was stirred at 0° C. for 10 minutes before the addition of iodine (2.57 g, 10.1 mmol). After stirring at room temperature with protection from light for 18 hours, the reaction was diluted with saturated sodium bicarbonate. The aqueous mixture was extracted three times with EtOAc. The combined organic extracts were washed with brine, dried over sodium sulfate, filtered and concentrated. The crude product was purified by flash chromatography (5% MeOH in DCM) to give 3-iodo-6-fluoroindole as a red solid (1.44 g, 65.4%).

Workup

  1. extractionThe aqueous mixture was extracted three times with EtOAc
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by flash chromatography (5% MeOH in DCM)

Sources & evidence

ORD record
ord-15bb4b59d70a48edbfbc67ba9bab6603
Source dataset
uspto-grants-2012_04
Patent number
US08158625B2

Reaction notes

Loading…