Cesium carbonate → 5-Bromo-6-methyl-1-(2,2,2-trifluoroethyl)pyridin-2(1H)-one
Reaction equation
[Br:1][C:2]1[C:3]([CH3:9])=[N:4][C:5]([OH:8])=[CH:6][CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O([CH2:24][C:25]([F:28])([F:27])[F:26])S(C(F)(F)F)(=O)=O>O1CCOCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5](=[O:8])[N:4]([CH2:24][C:25]([F:28])([F:27])[F:26])[C:3]=1[CH3:9]Participants
5
Conditions
- Temperature
- 50 °C
Procedure
To a stirred mixture of 3-bromo-6-hydroxy-2-methylpyridine (25.0 g, 133 mmol) and cesium carbonate (52.0 g, 160 mmol) in 1,4-dioxane (600 mL) was added 2,2,2-trifluoroethyl triflate (40.1 g, 173 mmol) and the resulting mixture was heated at 50° C. for 4 h and then allowed to cool to ambient temperature. The resulting mixture was filtered and the filtrate was concentrated to dryness in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of CH2Cl2:EtOAc—100:0 to 60:40, to give the title compound. MS: m/z=269.9 (M+1).
Workup
- temperatureto cool to ambient temperature
- filtrationThe resulting mixture was filtered
- concentrationthe filtrate was concentrated to dryness in vacuo
- customThe crude product was purified by silica gel chromatography
- washeluting with a gradient of CH2Cl2
Sources & evidence
- ORD record
- ord-26cc63318bbf4203a78bfb4d28936ffd
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08481556B2
Reaction notes
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