Sodium Hydroxide → 5-Cyclopropyl-7-[(2,6-difluorobenzyl)oxy]-2-methylpyrazolo[1,5-a]pyridine-3-carboxylic Acid
Reaction equation
[OH-].[Na+].C([O:5][C:6]([C:8]1[C:9]([CH3:30])=[N:10][N:11]2[C:16]([O:17][CH2:18][C:19]3[C:24]([F:25])=[CH:23][CH:22]=[CH:21][C:20]=3[F:26])=[CH:15][C:14]([CH:27]3[CH2:29][CH2:28]3)=[CH:13][C:12]=12)=[O:7])C.C[Si](C)(C)[O-].[K+]>CO>[CH:27]1([C:14]2[CH:15]=[C:16]([O:17][CH2:18][C:19]3[C:20]([F:26])=[CH:21][CH:22]=[CH:23][C:24]=3[F:25])[N:11]3[N:10]=[C:9]([CH3:30])[C:8]([C:6]([OH:7])=[O:5])=[C:12]3[CH:13]=2)[CH2:28][CH2:29]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
1.8 ml (1.8 mmol) of a 1 M aqueous solution of sodium hydroxide were added to a solution of 180 mg (0.47 mmol) of 5-cyclopropyl-7-(2,6-difluorobenzyloxy)-2-methylpyrazolo[1,5-a]pyridine-3-carboxylic acid ethyl ester (Example 148A) in 18 ml of methanol. The reaction was stirred at reflux for 18 h and concentrated under reduced pressure. The residue was taken up in 4 ml of tetrahydrofuran, and 70 mg (0.55 mmol) of potassium trimethylsilanolate were added. The reaction mixture was stirred at 65° C. for 18 h and concentrated under reduced pressure, which gave the target compound, which was used directly in the next step.
Workup
- temperatureat reflux for 18 h
- concentrationconcentrated under reduced pressure
- stirringThe reaction mixture was stirred at 65° C. for 18 h
- concentrationconcentrated under reduced pressure, which
- customgave the target compound, which
Sources & evidence
- ORD record
- ord-64c5eee6ebef453b88d4943abda2c5d4
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09422285B2
Reaction notes
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