Cesium carbonate → 2,5-Dichloro-4-(2,2,2-trifluoroethoxy)pyridine
Reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([OH:8])[C:5]([Cl:9])=[CH:4][N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].FC(F)(F)S(O[CH2:22][C:23]([F:26])([F:25])[F:24])(=O)=O>CN(C=O)C.C(OC(=O)C)C>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH2:22][C:23]([F:26])([F:25])[F:24])[C:5]([Cl:9])=[CH:4][N:3]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 90 °C
Procedure
To a solution of 2,5-dichloropyridin-4-ol (CAN 847664-65-7, 1.5 g, 9.15 mmol) in DMF (15 ml) in a microwave vial were added cesium carbonate (4.47 g, 13.7 mmol) and 2,2,2-trifluoroethyl trifluoromethanesulfonate (3.18 g, 13.7 mmol). The vial was sealed and heated at 90° C. overnight. The reaction mixture was diluted with ethylacetate and extracted with water. The organic phase was collected and the aqueous phase was back-extracted with ethylacetate. Organic phases were combined, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by flash chromatography eluting with a heptane/ethylacetate gradient on silica to yield the titled compound as a colorless oil (1.33 g, 59%). MS (ESI, m/z): 246.2 (M+H+).
Workup
- customThe vial was sealed
- extractionextracted with water
- customThe organic phase was collected
- extractionthe aqueous phase was back-extracted with ethylacetate
- dry with materialdried over magnesium sulfate
- concentrationconcentrated in vacuo
- customThe residue was purified by flash chromatography
- washeluting with a heptane/ethylacetate gradient on silica
Sources & evidence
- ORD record
- ord-cc66c43985224823a86e3bd9dd848f5a
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09409866B2
Reaction notes
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