Potassium Hydroxide → 3-Naphthalen-1-yl-imidazo[1,5-a]pyridine-1-carboxylic acid

HRID 1783774Notes

Reaction equation

HRID 1783774 reaction equation
FC(F)(F)[C:3]([C:5]1[N:6]=[C:7]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=[CH:16][CH:15]=2)[N:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=12)=[O:4].[OH-:26].[K+]>CCO>[C:14]1([C:7]2[N:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]3=[C:5]([C:3]([OH:26])=[O:4])[N:6]=2)[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 249480202,2,2-Trifluoro-1-(3-naphthalen-1-yl-imidazo[1,5-a]pyridin-1-yl)-ethanone

Product 1

HCID 249480213-Naphthalen-1-yl-imidazo[1,5-a]pyridine-1-carboxylic acidYield 55%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2,2,2-trifluoro-1-(3-naphthalen-1-yl-imidazo[1,5-a]pyridin-1-yl)-ethanone (260 mg, 0.76 mmol) in EtOH (10 mL) was added KOH (582 mg, 10.4 mmol) and the mixture was heated to reflux for 30 min. The mixture was allowed to cool and concentrated. The residue was dissolved in water (25 mL) and acidified to pH 3 with 2N HCl. The precipitate was filtered, dried and recrystallized from ethyl acetate to yield the title compound (120 mg, 55%). 8.30 (1H), 8.10 (2H), 7.78 (2H), 7.70 (1H), 7.59 (2H), 7.52 (1H), 7.02 (1H), 6.70 (1H); m/z (M+H)=289.24.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 30 min
  3. temperatureto cool
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in water (25 mL)
  6. filtrationThe precipitate was filtered
  7. customdried
  8. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-9ba2a1d370cb4c7aaf54abc6e7c021cb
Source dataset
uspto-grants-2009_03
Patent number
US07501438B2

Reaction notes

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