Acetic Acid → 8-Chloro-5-(3-fluorophenyl)imidazo[1,5-a]pyridine-6-carboxylic acid

HRID 717820Notes

Reaction equation

HRID 717820 reaction equation
[Cl:1][C:2]1[C:3]2[N:4]([CH:19]=[N:20][CH:21]=2)[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)=[C:6]([C:8]([O:10]C)=[O:9])[CH:7]=1.[OH-].[Na+].O.C(O)(=O)C>CO>[Cl:1][C:2]1[C:3]2[N:4]([CH:19]=[N:20][CH:21]=2)[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)=[C:6]([C:8]([OH:10])=[O:9])[CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 58515979Methyl 8-chloro-5-(3-fluorophenyl)imidazo[1,5-a]pyridine-6-carboxylate

Product 1

HCID 585159988-Chloro-5-(3-fluorophenyl)imidazo[1,5-a]pyridine-6-carboxylic acidYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 8-chloro-5-(3-fluorophenyl)imidazo[1,5-a]pyridine-6-carboxylate (0.60 g, 2.0 mmol) was stirred in methanol (40 mL) and a solution of 3 N sodium hydroxide in water (10 mL, 40 mmol) was added. The mixture was stirred for 16 hours at room temperature, and glacial acetic acid (5 mL) was added. Evaporation gave a precipitate which was filtered and washed with water to give the desired compound (0.29 g, 50%). LCMS calculated for C14H9ClFN2O2 (M+H)+: m/z=291.1. found: 290.9. 1H NMR (300 MHz, DMSO-d6): δ 7.77 (s, 1H), 7.60 (m, 2H), 7.40 (m, 4H).

Workup

  1. customEvaporation
  2. customgave a precipitate which
  3. filtrationwas filtered
  4. washwashed with water

Sources & evidence

ORD record
ord-02d8e7b44c9d44acb727b2bfd78c8d0e
Source dataset
uspto-grants-2015_11
Patent number
US09193721B2

Reaction notes

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