Potassium Hydroxide → 5-Fluoro-1-(pyridin-4-ylmethyl)-1H-indole-2-carboxylic acid

HRID 2041952Notes

Reaction equation

HRID 2041952 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=1)[C:6]([C:18]([O:20]CC)=[O:19])=[CH:5]2.[OH-].[K+]>C(O)C.O>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:13]=[CH:14][N:15]=[CH:16][CH:17]=1)[C:6]([C:18]([OH:20])=[O:19])=[CH:5]2

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 15978981ethyl 5-fluoro-1-[(pyridin-4-yl)methyl]-1H-indole-2-carboxylate

Product 1

HCID 574315345-Fluoro-1-(pyridin-4-ylmethyl)-1H-indole-2-carboxylic acidYield 78.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 2.1 g (7.04 mmol) of ethyl 5-fluoro-1-[(pyridin-4-yl)methyl]-1H-indole-2-carboxylate (WO 2007/010144) and of 1.18 g (21.12 mmol) of potassium hydroxide in 80 ml of ethanol and 2 ml of water is refluxed for 2 hours. The reaction mixture is subsequently concentrated under reduced pressure. 100 ml of water are added and the pH of the solution is brought to pH 8 by the addition of a concentrated hydrochloric acid solution. A precipitate is recovered by filtration and is washed with water and then dried under reduced pressure. 1.5 g of the expected product are thus obtained.

Workup

  1. concentrationThe reaction mixture is subsequently concentrated under reduced pressure
  2. addition100 ml of water are added
  3. additionthe pH of the solution is brought to pH 8 by the addition of a concentrated hydrochloric acid solution
  4. filtrationA precipitate is recovered by filtration
  5. washis washed with water
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-5e0ab98c209c419aa773d46606ddb3fb
Source dataset
uspto-grants-2013_11
Patent number
US08586573B2

Reaction notes

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