Acetic Acid → 5-Methanesulfonyl-1H-indole-2-carboxylic acid

HRID 1060829

Reaction equation

HRID 1060829 reaction equation
C[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].[Li+].[OH-].C(O)(=O)C>C1COCC1.O>[CH3:17][S:14]([C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[NH:6][C:5]([C:3]([OH:4])=[O:2])=[CH:13]2)(=[O:16])=[O:15]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 3939Lithium HydroxideHCID 735868Methyl 5-(methylsulfonyl)-1H-indole-2-carboxylate

Product 1

HCID 223944465-Methanesulfonyl-1H-indole-2-carboxylic acidYield 23.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the 5-methanesulfonyl-1H-indole-2-carboxylic acid methyl ester (0.49 g) in THF (12 mL) and water (4 ml) was added LiOH (0.098 g). The reaction mixture was left to stir for 2 hours. Acetic acid was added and the product extracted with dichloromethane. The organic extracts were combined, dried with magnesium sulfate, filtered and the filtrate evaporated to give the title compound as a solid (0.110 g).

Workup

  1. waitThe reaction mixture was left
  2. extractionthe product extracted with dichloromethane
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. customthe filtrate evaporated

Sources & evidence

ORD record
ord-413d223ba2964730b9e0f10bcb1b678a
Source dataset
uspto-grants-2003_02
Patent number
US06525070B2

Linked notes

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