Benzenesulfonyl chloride → HCID 18765369, compound

HRID 480570Notes

Reaction equation

HRID 480570 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][C:17]=1[O:18][CH3:19])[NH:14][CH:13]=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[C:22]1([S:28](Cl)(=[O:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.CCOC(C)=O>CN(C=O)C>[C:22]1([S:28]([N:14]2[C:15]3[C:11](=[CH:10][C:9]([O:8][CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)=[C:17]([O:18][CH3:19])[CH:16]=3)[CH:12]=[CH:13]2)(=[O:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 7369Benzenesulfonyl chlorideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 2608005-Benzyloxy-6-methoxyindole

Product 1

HCID 18765369HCID 18765369, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 5-benzyloxy-6-methoxyindole (990 mg, 3.9 mmol) in DMF (3 mL) was added to a solution of NaH (234 mg, 5.9 mmol, 60% in oil) in DMF (1 mL) at 0° C. The ice bath was removed, and the reaction mixture allowed to stir at RT for 30 min. The reaction flask was cooled to 0° C. and PhSO2Cl (0.6 mL, 4.7 mmol) was added via syringe. The ice bath was removed and the reaction mixture stirred at RT for 24 h. Water (25 mL) was added and the aqueous layer extracted with Et2O (4×50 mL). The combined organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to give an oil. The residue was purified by column chromatography (25% then 40% EtOAc/hex) to furnish N-phenylsulfonyl 5-benzyloxy-6-methoxyindole as a crystalline solid (1.38 g, 90% yield).

Workup

  1. customThe ice bath was removed
  2. temperatureThe reaction flask was cooled to 0° C.
  3. customThe ice bath was removed
  4. stirringthe reaction mixture stirred at RT for 24 h
  5. additionWater (25 mL) was added
  6. extractionthe aqueous layer extracted with Et2O (4×50 mL)
  7. washThe combined organic extracts were washed with brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customto give an oil
  12. customThe residue was purified by column chromatography (25%

Sources & evidence

ORD record
ord-9ee03281ec22404eb947fe151ad67641
Source dataset
uspto-grants-2003_11
Patent number
US06653304B2

Reaction notes

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