Hydrochloric Acid → 5-Fluoro-1-(methylsulfonyl)-1H-indole-3-carboxylic acid

HRID 624662Notes

Reaction equation

HRID 624662 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:11]([CH3:14])(=[O:13])=[O:12])[CH:6]=[C:5]2[C:15]([O:17]C(C)(C)C)=[O:16].Cl>CCOC(C)=O>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:11]([CH3:14])(=[O:13])=[O:12])[CH:6]=[C:5]2[C:15]([OH:17])=[O:16]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 90031845tert-Butyl 5-fluoro-1-(methylsulfonyl)-1H-indole-3-carboxylate

Product 1

HCID 900309845-Fluoro-1-(methylsulfonyl)-1H-indole-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of tert-butyl 5-fluoro-1-(methylsulfonyl)-1H-indole-3-carboxylate (150 mg, 0.479 mmol) and conc. HCl (0.2 ml, 2.394 mmol) in EtOAc (10 ml) was stirred at RT for 2 h. The mixture was then partially concentrated, and the resulting precipitate was collected by filtration, washed with EtOAc and dried in vacuo to afford the title compound as a white solid, which was used without further purification.

Workup

  1. concentrationThe mixture was then partially concentrated
  2. filtrationthe resulting precipitate was collected by filtration
  3. washwashed with EtOAc
  4. customdried in vacuo

Sources & evidence

ORD record
ord-0274125a8df04815ab79ff8755cea993
Source dataset
uspto-grants-2016_04
Patent number
US09303045B2

Reaction notes

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