Cesium carbonate → 4-Bromo-1-(oxetan-3-YL)-1H-pyrazole
Reaction equation
[Br:1][C:2]1[CH:3]=[N:4][NH:5][CH:6]=1.Br[CH:8]1[CH2:11][O:10][CH2:9]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[Br:1][C:2]1[CH:3]=[N:4][N:5]([CH:8]2[CH2:11][O:10][CH2:9]2)[CH:6]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 130 °C
Procedure
4-Bromo-1H-pyrazole (1.53 g, 10.7 mmol) is dissolved in anhydrous dimethylformamide (15 mL). 3-Bromooxetane (2.0 g, 14.6 mmol) and caesium carbonate (4.7 g, 14 mmol) are successively added thereto. The reaction mixture is heated for 8 hours at 130° C. in a sealed flask. At the end of the reaction, the solvent is evaporated off in vacuo and the residue is purified by chromatography over silica gel using dichloromethane containing diethylamine and methanol as eluants to yield the expected compound.
Workup
- customAt the end of the reaction
- customthe solvent is evaporated off in vacuo
- customthe residue is purified by chromatography over silica gel
- additioncontaining diethylamine and methanol as eluants
Sources & evidence
- ORD record
- ord-fc3f1cb3d3e44a0babd9c31d566c8cf5
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09108983B2
Reaction notes
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