Potassium Hydroxide → 5-Trifluoromethyl-1-[(4-pyridyl)methyl]-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid

HRID 1019533Notes

Reaction equation

HRID 1019533 reaction equation
[OH-].[K+].[F:3][C:4]([F:22])([F:21])[C:5]1[CH:6]=[C:7]2[CH:13]=[CH:12][N:11]([CH2:14][C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)[C:8]2=[N:9][CH:10]=1.CC[C:25]([O-:27])=[O:26]>O.C(O)C>[F:22][C:4]([F:21])([F:3])[C:5]1[CH:6]=[C:7]2[CH:13]=[C:12]([C:25]([OH:27])=[O:26])[N:11]([CH2:14][C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)[C:8]2=[N:9][CH:10]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 866390585-trifluoromethyl-1-[(4-pyridyl)methyl]-1H-pyrrolo[2,3-b]pyridine 2-ethyl carboxylate

Product 1

HCID 666469215-Trifluoromethyl-1-[(4-pyridyl)methyl]-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acidYield 73.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 0.39 g (6.87 mmol) of potassium hydroxide in 2 mL of water is added to a solution, in 30 mL of ethanol, of 0.8 g (2.29 mmol) of 5-trifluoromethyl-1-[(4-pyridyl)methyl]-1H-pyrrolo[2,3-b]pyridine-2-ethyl carboxylate, obtained in Stage 9.1. The mixture is stirred for four hours under reflux. After this time the reaction mixture is concentrated at reduced pressure, and is then taken up in 40 mL of water. The reaction mixture is acidified to pH 5 by successive additions of concentrated hydrochloric acid. The precipitate is collected by filtration, washed with water and then dried at reduced pressure. In this way we isolate 0.54 g of the expected product, in the form of a white powder, which is used as it is in the next stage.

Workup

  1. customobtained in Stage 9.1
  2. temperatureunder reflux
  3. concentrationAfter this time the reaction mixture is concentrated at reduced pressure
  4. filtrationThe precipitate is collected by filtration
  5. washwashed with water
  6. customdried at reduced pressure

Sources & evidence

ORD record
ord-485df4b1d5d04f0f9ba2095673be4769
Source dataset
uspto-grants-2014_05
Patent number
US08716272B2

Reaction notes

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