Potassium Hydroxide → 3-(4-Fluorophenyl)imidazo[1,5-a]pyridine-8-carboxylic acid

HRID 1423014Notes

Reaction equation

HRID 1423014 reaction equation
C([O:3][C:4]([C:6]1[C:7]2[N:8]([C:12]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)=[N:13][CH:14]=2)[CH:9]=[CH:10][CH:11]=1)=[O:5])C.[OH-].[K+]>CO.O>[F:21][C:18]1[CH:17]=[CH:16][C:15]([C:12]2[N:8]3[CH:9]=[CH:10][CH:11]=[C:6]([C:4]([OH:5])=[O:3])[C:7]3=[CH:14][N:13]=2)=[CH:20][CH:19]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 683454063-(4-Fluorophenyl)-imidazo[1,5-a]pyridine-8-carboxylic acid ethyl ester

Product 1

HCID 671947383-(4-Fluorophenyl)imidazo[1,5-a]pyridine-8-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 3-(4-fluorophenyl)-imidazo[1,5-a]pyridine-8-carboxylic acid ethyl ester (290 mg, 1.0 mmol) in methanol (20 mL) is added a solution of 85% potassium hydroxide pellets (0.300 g, 3.92 mmol) in water (5.0 mL). The reaction mixture is warmed at reflux for 5 minutes, cooled to room temperature and concentrated in vacuo to remove excess methanol. The mixture is acidified to pH 4 with 1 N aqueous HCl and the resulting precipitate is collected by filtration, washed with water and dried to afford the title product.

Workup

  1. temperatureThe reaction mixture is warmed
  2. temperatureat reflux for 5 minutes
  3. concentrationconcentrated in vacuo
  4. customto remove excess methanol
  5. filtrationthe resulting precipitate is collected by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-380ca5d6c7674347bcf1da703b2421a6
Source dataset
uspto-grants-2015_01
Patent number
US08927550B2

Reaction notes

Loading…