2-Trifluoromethyl-4-(1-hydroxyethyl)-7-methoxy-pyrazolo[1,5-a]pyridine → 4-Acetyl-2-trifluoromethyl-7-methoxy-pyrazolo[1,5-a]pyridine
Reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:16]=[C:6]2[C:7]([CH:13]([OH:15])[CH3:14])=[CH:8][CH:9]=[C:10]([O:11][CH3:12])[N:5]2[N:4]=1>ClCCl.[O-2].[O-2].[Mn+4]>[C:13]([C:7]1[C:6]2[N:5]([N:4]=[C:3]([C:2]([F:1])([F:18])[F:17])[CH:16]=2)[C:10]([O:11][CH3:12])=[CH:9][CH:8]=1)(=[O:15])[CH3:14]Participants
Procedure
The compound of Example 134 (1.64 g) was dissolved in dichloromethane (30.0 mL). To this solution, activated manganese dioxide (5.48 g) was added and the mixture was stirred at room temperature for 16 hours. Subsequently, a second portion of activated manganese dioxide (5.48 g) was added and the mixture was stirred at room temperature for 10 hours. A third portion of activated manganese dioxide (5.48 g) was then added and the mixture was stirred at room temperature for 10.5 hours. Finally, a fourth portion of activated manganese dioxide (2.74 g) was added and the mixture was stirred for 13.5 hours. Subsequently, the reaction mixture was filtered through Celite and the filtrate was evaporated to afford the title compound as a pale yellow powder (1.08 g).
Workup
- additionwas added
- stirringthe mixture was stirred at room temperature for 10 hours
- stirringthe mixture was stirred at room temperature for 10.5 hours
- stirringthe mixture was stirred for 13.5 hours
- filtrationSubsequently, the reaction mixture was filtered through Celite
- customthe filtrate was evaporated
Sources & evidence
- ORD record
- ord-b3886fbdbb674471b20ea1513c25a78b
- Source dataset
- uspto-grants-2010_07
- Patent number
- US07763617B2
Reaction notes
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