Hydrochloric Acid → Methyl 5-(methylsulfonyl)-1H-indole-2-carboxylate

HRID 1838358Notes

Reaction equation

HRID 1838358 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6](S(C2C=CC=CC=2)(=O)=O)[C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:9][CH:8]=2)=[O:4].O1CCCC1.[OH-].[K+].Cl>CO>[CH3:1][O:2][C:3]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:9][CH:8]=2)=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 684443721-Benzenesulfonyl-5-methanesulfonylindole-2-carboxylic acid methyl ester

Product 1

HCID 735868Methyl 5-(methylsulfonyl)-1H-indole-2-carboxylateYield 97.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of the resulting 1-benzenesulfonyl-5-methanesulfonylindole-2-carboxylic acid methyl ester (3.5 g), tetrahydrofuran (45 ml) and methanol (12 ml), potassium hydroxide (0.79 g) was added at 0° C. and the mixture was stirred at the same temperature for 3 hours. 2N hydrochloric acid was added, and the mixture was extracted with dichloromethane. The organic layer was washed with water and dried over sodium sulfate. The solvent was distilled off under reduced pressure to obtain 2.2 g of a white amorphous 5-methanesulfonylindole-2-carboxylic acid methyl ester as a crude product.

Workup

  1. additionwas added at 0° C.
  2. extractionthe mixture was extracted with dichloromethane
  3. washThe organic layer was washed with water
  4. dry with materialdried over sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-e0a65c5039714c168d06dae4c9617d8c
Source dataset
uspto-grants-2004_01
Patent number
US06673797B1

Reaction notes

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