Potassium Hydroxide → HCID 67196007, compound

HRID 1423025Notes

Reaction equation

HRID 1423025 reaction equation
C([O:3][C:4]([C:6]1[C:7]2[CH:14]=[CH:13][N:12]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[C:8]=2[CH:9]=[N:10][CH:11]=1)=[O:5])C.[OH-].[K+]>CO.O>[F:21][C:18]1[CH:17]=[CH:16][C:15]([N:12]2[C:8]3[CH:9]=[N:10][CH:11]=[C:6]([C:4]([OH:5])=[O:3])[C:7]=3[CH:14]=[CH:13]2)=[CH:20][CH:19]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 671974811H-Pyrrolo[2,3-c]pyridine-4-carboxylic acid, 1-(4-fluorophenyl)-, ethyl ester

Product 1

HCID 67196007HCID 67196007, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of 1-(4-fluorophenyl)-1H-pyrrolo[2,3-c]pyridine-4-carboxylic acid ethyl ester (650 mg, 2.3 mmol) in methanol (25 mL) is added in several portions a solution of 85% KOH (1.2 g, 18.2 mmol) in water (15 mL). The mixture is warmed at reflux for 30 minutes and is then diluted with water (20 mL) and washed with ether (2×15 mL). The aqueous layer is made acidic (pH=4) with concentrated HCl and the resulting precipitate is collected by filtration washing with water to afford the title compound.

Workup

  1. temperatureThe mixture is warmed
  2. temperatureat reflux for 30 minutes
  3. washwashed with ether (2×15 mL)
  4. filtrationthe resulting precipitate is collected by filtration
  5. washwashing with water

Sources & evidence

ORD record
ord-488212bc9591491aa270031478f62c0b
Source dataset
uspto-grants-2015_01
Patent number
US08927550B2

Reaction notes

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