Benzenesulfonyl chloride → 5-Fluoro-1-(phenylsulfonyl)-1H-indole

HRID 503914Notes

Reaction equation

HRID 503914 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[K+].[F:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][CH:16]=[CH:15]2.[C:21]1([S:27](Cl)(=[O:29])=[O:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C=O)C>[C:21]1([S:27]([N:17]2[C:18]3[C:14](=[CH:13][C:12]([F:11])=[CH:20][CH:19]=3)[CH:15]=[CH:16]2)(=[O:29])=[O:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 678615-FluoroindoleHCID 3251421Potassium bis(trimethylsilyl)amide

Product 1

HCID 112888585-Fluoro-1-(phenylsulfonyl)-1H-indoleYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

KHMDS (0.5 M in toluene, 23 mL, 11.65 mmol) was added at 0° C. to a solution of 5-fluoroindole (1.5 g, 11.09 mmol) in DMF (23 mL). After stirring for 10 minutes, benzenesulfonyl chloride (1.55 mL, 12.209 mmol) was added. The ice-bath was removed and the mixture was stirred at room temperature for 4 hours. A saturated solution of NH4Cl was added to the reaction, and the resulting mixture was extracted with EtOAc. The combined organic extracts were washed with water and brine; dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was recrystallized from toluene to afford 2.26 g (74% yield) of 1-benzenesulfonyl-5-fluoro-1H-indole as a white solid.

Workup

  1. customThe ice-bath was removed
  2. stirringthe mixture was stirred at room temperature for 4 hours
  3. additionA saturated solution of NH4Cl was added to the reaction
  4. extractionthe resulting mixture was extracted with EtOAc
  5. washThe combined organic extracts were washed with water and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customThe residue was recrystallized from toluene

Sources & evidence

ORD record
ord-fdc0db041e3c4731bbd8402309b37211
Source dataset
uspto-grants-2010_08
Patent number
US07776910B2

Reaction notes

Loading…