Sodium Hydroxide → 6-Chloro-1-(3,5-difluorophenyl)-1H-indole-3-carboxylic acid

HRID 1716426Notes

Reaction equation

HRID 1716426 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:19](=[O:24])C(F)(F)F)=[CH:7][N:8]2[C:11]2[CH:16]=[C:15]([F:17])[CH:14]=[C:13]([F:18])[CH:12]=2)=[CH:4][CH:3]=1.[OH-:25].[Na+]>>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:19]([OH:24])=[O:25])=[CH:7][N:8]2[C:11]2[CH:16]=[C:15]([F:17])[CH:14]=[C:13]([F:18])[CH:12]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 866101631-[6-Chloro-1-(3,5-difluoro-phenyl)-1H-indol-3-yl]-2,2,2-trifluoro-ethanone

Product 1

HCID 685076036-Chloro-1-(3,5-difluorophenyl)-1H-indole-3-carboxylic acidYield 70%

Conditions

Temperature
70 °C

Procedure

A suspension of 1-[6-chloro-1-(3,5-difluoro-phenyl)-1H-indol-3-yl]-2,2,2-trifluoro-ethanone in 3N aqueous NaOH was stirred at 70° C. for 48 h. After washing with CH2Cl2, the aqueous phase was acidified to pH 1 and extracted with CH2Cl2. Concentration in vacuo gave the title compound in 70% yield.

Workup

  1. washAfter washing with CH2Cl2
  2. extractionextracted with CH2Cl2
  3. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-620f921d914144b19484cc26b48144fb
Source dataset
uspto-grants-2010_09
Patent number
US07803815B2

Reaction notes

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