Benzenesulfonyl chloride → 1-Benzenesulfonyl-7-methoxy-1H-indole

HRID 240909

Reaction equation

HRID 240909 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][CH:9]=[CH:8]2.[H-].[Na+].[C:14]1([S:20](Cl)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O.C(OCC)(=O)C>CN(C=O)C>[C:14]1([S:20]([N:10]2[C:11]3[C:7](=[CH:6][CH:5]=[CH:4][C:3]=3[O:2][CH3:1])[CH:8]=[CH:9]2)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 766607-Methoxy-1H-indoleHCID 22728543Water ethylacetate

Product 1

HCID 117788011-Benzenesulfonyl-7-methoxy-1H-indole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-methoxyindole (1 eq) in DMF cooled in an ice bath was added NaH (60% dispersion in oil, 1.2 eq). The reaction was stirred for 1 hr at room temperature then recooled in an ice bath. Benzenesulfonyl chloride (1.1 eq) was added then the reaction was stirred for 2 hrs at room temperature. Water/ethyl acetate were added and the ethyl acetate layer was washed repeatedly (3×) with water. The ethyl acetate layer was concentrated and evaporated to dryness.

Workup

  1. customthen recooled in an ice bath
  2. stirringthe reaction was stirred for 2 hrs at room temperature
  3. washthe ethyl acetate layer was washed repeatedly (3×) with water
  4. concentrationThe ethyl acetate layer was concentrated
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-927b9b30e72649e2b62c4b069c86d747
Source dataset
uspto-grants-2014_02
Patent number
US08648104B2

Linked notes

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