Benzenesulfonyl chloride → HCID 67273214, compound

HRID 1020915Notes

Reaction equation

HRID 1020915 reaction equation
[CH3:1][O:2][C:3]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[CH:6][NH:7]2.[H-].[Na+].[C:16]1([S:22](Cl)(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1COCC1>[C:16]1([S:22]([N:7]2[C:8]3[C:4](=[C:3]([O:2][CH3:1])[C:11]([O:12][CH3:13])=[CH:10][CH:9]=3)[CH:5]=[CH:6]2)(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 19616134,5-dimethoxy-1H-indole

Product 1

HCID 67273214HCID 67273214, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 4,5-dimethoxyindole (241 mg, 1.36 mmol) in 5 mL THF at 0° C. was added 82 mg (2.04 mmol, 1.5 eq) of sodium hydride, followed by benzenesulfonyl chloride (260 μL, 2.04 mmol, 1.5 eq). The reaction was warmed to room temperature over 5 h then quenched with H2O and concentrated. The residue was dissolved in CH2Cl2 and extracted with NaHCO3, H2O, aqueous NaCl, dried (Na2SO4), and concentrated. The product was purified by silica gel column chromatography (7/3 hexanes/EtOAc) to give 369 mg of 1-benzenesulfonyl-4,5-dimethoxy-1H-indole (86%).

Workup

  1. customthen quenched with H2O
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in CH2Cl2
  4. extractionextracted with NaHCO3, H2O, aqueous NaCl
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe product was purified by silica gel column chromatography (7/3 hexanes/EtOAc)

Sources & evidence

ORD record
ord-b47f0ec2eea14c5a800eb6a89605eeda
Source dataset
uspto-grants-2014_05
Patent number
US08716493B2

Reaction notes

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