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

HRID 448827Notes

Reaction equation

HRID 448827 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-ylmethyl)-1H-indole-2-carboxylate and 1.18 g (21.12 mmol) of potassium hydroxide in 80 ml of ethanol and 2 ml of water is heated at reflux 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 addition of a concentrated hydrochloric acid solution. A precipitate is collected 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. temperatureat reflux for 2 hours
  2. concentrationThe reaction mixture is subsequently concentrated under reduced pressure
  3. addition100 ml of water are added
  4. additionthe pH of the solution is brought to pH 8 by addition of a concentrated hydrochloric acid solution
  5. filtrationA precipitate is collected by filtration
  6. washis washed with water
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-3c4e86fb75d04274b5ef3ef285405139
Source dataset
uspto-grants-2013_07
Patent number
US08481745B2

Reaction notes

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