Potassium Hydroxide → HCID 67195772, compound

HRID 1423037Notes

Reaction equation

HRID 1423037 reaction equation
C([O:3][C:4]([C:6]1[N:11]2[CH:12]=[N:13][C:14]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)=[C:10]2[CH:9]=[CH:8][CH:7]=1)=[O:5])C.[OH-].[K+]>CO.O>[F:21][C:18]1[CH:17]=[CH:16][C:15]([C:14]2[N:13]=[CH:12][N:11]3[C:6]([C:4]([OH:5])=[O:3])=[CH:7][CH:8]=[CH:9][C:10]=23)=[CH:20][CH:19]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 67196685HCID 67196685, compound

Product 1

HCID 67195772HCID 67195772, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 1-(4-fluorophenyl)-imidazo[1,5-a]pyridine-5-carboxylic acid ethyl ester (2.0 g, 7.0 mmol) in MeOH (233 mL) is added a solution of 85% KOH (4.6 g, 69 mmol) in H2O (35 mL) and the mixture is warmed at reflux. After 15 minutes, the reaction mixture is evaporated, diluted with water, and washed with EtOAc (2×200 mL). The aqueous layer is acidified with 1 N aqueous HCl (pH 5-6) to afford a precipitate. The solid is collected by filtration and triturated with 10% MeOH—CH2Cl2 to provide the title compound.

Workup

  1. temperaturethe mixture is warmed
  2. temperatureat reflux
  3. customthe reaction mixture is evaporated
  4. additiondiluted with water
  5. washwashed with EtOAc (2×200 mL)
  6. customto afford a precipitate
  7. filtrationThe solid is collected by filtration
  8. customtriturated with 10% MeOH—CH2Cl2

Sources & evidence

ORD record
ord-fc2fad5da4514786a4bd80e30a20b029
Source dataset
uspto-grants-2015_01
Patent number
US08927550B2

Reaction notes

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