Iodine → 5,6-difluoro-3-iodo-1H-indole

HRID 2274773Notes

Reaction equation

HRID 2274773 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[NH:7][CH:6]=[CH:5]2.[OH-].[K+].[I:14]I>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[NH:7][CH:6]=[C:5]2[I:14]

Participants

5

Reactant 3

HCID 807IodineHCID 14797Potassium HydroxideHCID 27787325,6-Difluoro-1H-indole

Product 1

HCID 1180604165,6-difluoro-3-iodo-1H-indoleYield 101.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a mixture of 5,6-difluoro-1H-indole (500 mg; 3.27 mmol) and KOH (458 mg; 8.18 mmol) in DMF (6.2 mL) was added a solution of iodine (837.5 mg; 3.3 mmol) in DMF (6.3 mL). The mixture was stirred at r.t. for 12 hours. It was poured into an ice-water mixture (60 mL) and extracted with EtOAc (20 mL×3). The combined organic layers was washed with brine (100 mL) and dried over anhydrous Na2SO4, filtered, concentrated to afford 930 mg (100%) of the title compound as a red solid. It was used to next step without further purification.

Workup

  1. extractionextracted with EtOAc (20 mL×3)
  2. washThe combined organic layers was washed with brine (100 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3d92e538886041eb8e954d26d8d240fa
Source dataset
uspto-grants-2015_09
Patent number
US09126984B2

Reaction notes

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