HCID 59389399, compound → 3-Chloro-2-ethyl-4-hydroxy-pyrazolo[1,5-a]pyridine
Reaction equation
[Cl:1][C:2]1[C:3]([CH2:13][CH3:14])=[N:4][N:5]2[CH:10]=[CH:9][CH:8]=[C:7]([O:11]C)[C:6]=12.[Br-].[Br-].[Br-].B>ClCCl>[Cl:1][C:2]1[C:3]([CH2:13][CH3:14])=[N:4][N:5]2[CH:10]=[CH:9][CH:8]=[C:7]([OH:11])[C:6]=12Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
The compound of Example 65 (3.07 g) was dissolved in dichloromethane (40 mL) in an argon atmosphere. While this solution was kept at 0° C., borane tribromide (17.6 mL, 1.0 mol/mL dichloromethane solution) was added and the mixture was stirred for 26 hours at 0° C. to reflux temperature. Subsequently, the reaction was terminated by adding water and the mixture was extracted three times with ethylacetate. The organic layer was washed with saturated brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure to afford the title compound as a yellow powder (2.91 g).
Workup
- customwas kept at 0° C.
- temperatureto reflux temperature
- customSubsequently, the reaction was terminated
- additionby adding water
- extractionthe mixture was extracted three times with ethylacetate
- washThe organic layer was washed with saturated brine
- dry with materialdried over sodium sulfate
- customThe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-90a9d65f845943babf6210b568f9ad1f
- Source dataset
- uspto-grants-2010_07
- Patent number
- US07763617B2
Reaction notes
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