Sodium Hydroxide → 7-[(2,6-Difluorobenzyl)oxy]-2-methylpyrazolo[1,5-a]pyridine-3-carboxylic Acid

HRID 1486296Notes

Reaction equation

HRID 1486296 reaction equation
C([O:3][C:4]([C:6]1[C:7]([CH3:25])=[N:8][N:9]2[C:14]([O:15][CH2:16][C:17]3[C:22]([F:23])=[CH:21][CH:20]=[CH:19][C:18]=3[F:24])=[CH:13][CH:12]=[CH:11][C:10]=12)=[O:5])C.[OH-].[Na+]>O1CCOCC1>[F:24][C:18]1[CH:19]=[CH:20][CH:21]=[C:22]([F:23])[C:17]=1[CH2:16][O:15][C:14]1[N:9]2[N:8]=[C:7]([CH3:25])[C:6]([C:4]([OH:5])=[O:3])=[C:10]2[CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 1178646217-[(2,6-Difluorobenzyl)oxy]-2-methylpyrazolo[1,5-a]pyridine-3-carboxylic Acid ethyl Ester

Product 1

HCID 1178595867-[(2,6-Difluorobenzyl)oxy]-2-methylpyrazolo[1,5-a]pyridine-3-carboxylic Acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 200 mg (0.228 mmol, 43% pure) of 7-[(2,6-difluorobenzyl)oxy]-2-methylpyrazolo[1,5-a]pyridine-3-carboxylic acid ethyl ester from Example 129A in 3 ml of dioxane was admixed with 1 ml of 2 N sodium hydroxide solution. The resulting mixture was stirred at room temperature for 72 h. The solvent was drawn off under reduced pressure and the residue was purified by flash chromatography using a prepacked silica gel cartridge (eluent:dichloromethane-methanol 100:1 to 10:1), which gave 100 mg (77% of theory, 61% pure) of the target compound.

Workup

  1. customthe residue was purified by flash chromatography
  2. customgave 100 mg (77% of theory, 61% pure) of the target compound

Sources & evidence

ORD record
ord-00e5807df01f46898173f4c3d37c6fd7
Source dataset
uspto-grants-2016_08
Patent number
US09422285B2

Reaction notes

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