Lithium Hydroxide → 4-(3,5-difluoro-phenoxy)-1H-indole-2-carboxylic acid

HRID 1929187Notes

Reaction equation

HRID 1929187 reaction equation
C([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[C:12]([O:15][C:16]1[CH:21]=[C:20]([F:22])[CH:19]=[C:18]([F:23])[CH:17]=1)[CH:11]=[CH:10][CH:9]=2)=[O:5])C.[Li+].[OH-]>CO.O>[F:23][C:18]1[CH:17]=[C:16]([CH:21]=[C:20]([F:22])[CH:19]=1)[O:15][C:12]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:13]=1[CH:14]=[C:6]([C:4]([OH:5])=[O:3])[NH:7]2

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 668414284-(3,5-Difluoro-phenoxy)-1H-indole-2-carboxylic acid ethyl ester

Product 1

HCID 668416404-(3,5-difluoro-phenoxy)-1H-indole-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

156 (260 mg, 0.82 mmol) is dissolved in 10 ml of methanol and treated with a solution of LiOH (40 mg, 1.6 mmol) in 5 ml of water. The mixture is stirred at room temperature for 18 hours. After evaporation, the crude product is acidified at 0° C. with 2M HCl and extracted with ethyl acetate. The organic layers are dried over sodium sulphate and evaporated.

Workup

  1. customAfter evaporation
  2. customis acidified at 0° C. with 2M HCl
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layers are dried over sodium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-f95e245b6b8c493ba8b6a8b752580b5d
Source dataset
uspto-grants-2012_05
Patent number
US08183366B2

Reaction notes

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