Benzenesulfonyl chloride → 5,6-difluoro-3-iodo-1-(phenylsulfonyl)-1H-indole

HRID 2274774Notes

Reaction equation

HRID 2274774 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]=[C:5]2[I:12].[H-].[Na+].[C:15]1([S:21](Cl)(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[N:7]([S:21]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:23])=[O:22])[CH:6]=[C:5]2[I:12]

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 1180604165,6-difluoro-3-iodo-1H-indole2×

Product 1

HCID 1180602835,6-difluoro-3-iodo-1-(phenylsulfonyl)-1H-indoleYield 72.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 5,6-difluoro-3-iodo-1H-indole (Intermediate 27; 930 mg; 3.33 mmol) in THF (20 mL) at 0° C. was added NaH (266.4 mg; 60%; 6.66 mmol) under nitrogen. The reaction mixture was stirred at r.t. for 15 minutes before a solution of benzenesulfonyl chloride (763.4 mg; 4.32 mmol) in THF (2 mL) was added dropwise. The reaction was stirred at r.t. for 12 hours, quenched with an ice-water mixture (60 mL) and extracted with EtOAc (30 mL×3). The combined organic layers were washed with brine (100 mL), dried over anhydrous Na2SO4, filtered, concentrated, and purified by a silica gel chromatography (petroleum ether/EtOAc=10/1-3/1) to afford 1.01 g (72%) of the title compound as a yellow solid.

Workup

  1. additionwas added dropwise
  2. customquenched with an ice-water mixture (60 mL)
  3. extractionextracted with EtOAc (30 mL×3)
  4. washThe combined organic layers were washed with brine (100 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by a silica gel chromatography (petroleum ether/EtOAc=10/1-3/1)

Sources & evidence

ORD record
ord-d1f273ecb1fa4caa8ad0d1150e364d70
Source dataset
uspto-grants-2015_09
Patent number
US09126984B2

Reaction notes

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