Dichloromethane → Ethyl 1-(benzenesulfonyl)indole-2-carboxylate

HRID 493244Notes

Reaction equation

HRID 493244 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([O:12][CH2:13][CH3:14])=[O:11].[H-].[Na+].[C:17]1([S:23](Cl)(=[O:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.ClCCl>CN(C=O)C.O>[C:17]1([S:23]([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:3]=[C:2]2[C:10]([O:12][CH2:13][CH3:14])=[O:11])(=[O:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 73125Ethyl indole-2-carboxylate

Product 1

HCID 506886Ethyl 1-(benzenesulfonyl)indole-2-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred and cooled (to about 0° C.) solution of ethyl indole-2-carboxylate 10 (1 eq.) in DMF (2 ml/mmol) under N2, was added NaH (60% in oil, 1.2 eq.) portionwise. When gas evolution stopped, benzenesulfonyl chloride (1.2 eq.) was added. The reaction mixture was stirred for about 1 hour (TLC monitoring, eluent dichloromethane); a small amount of water then was added carefully and the DMF was evaporated. The crude residue was dissolved in ethyl acetate and washed with water and brine. After drying and evaporation of the solvents, the compound was purified by chromatography on silica gel (eluent: C6H12/EtOAc 9/1 to 7/3) to give the ethyl 1-phenylsulfonylindole-2-carboxylate.

Workup

  1. customthe DMF was evaporated
  2. dissolutionThe crude residue was dissolved in ethyl acetate
  3. washwashed with water and brine
  4. customAfter drying
  5. customevaporation of the solvents
  6. customthe compound was purified by chromatography on silica gel (eluent: C6H12/EtOAc 9/1 to 7/3)

Sources & evidence

ORD record
ord-62e0074dd1bd46c7bde120c51108ea63
Source dataset
uspto-grants-2009_05
Patent number
US07534809B2

Reaction notes

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