Cesium carbonate → Methyl 5-fluoromethoxypyridine-2-carboxylate
Reaction equation
C1(C)C=CC(S(O[CH2:11][F:12])(=O)=O)=CC=1.[OH:14][C:15]1[CH:16]=[CH:17][C:18]([C:21]([O:23][CH3:24])=[O:22])=[N:19][CH:20]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[Cl-].[NH4+]>CN(C=O)C.C(OCC)(=O)C>[F:12][CH2:11][O:14][C:15]1[CH:16]=[CH:17][C:18]([C:21]([O:23][CH3:24])=[O:22])=[N:19][CH:20]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 70 °C
Procedure
A solution containing fluoromethyl toluene-4-sulfonate (233 mg) in DMF was added to a solution containing methyl 5-hydroxypyridine-2-carboxylate (100 mg) and cesium carbonate (532 mg) in DMF (5 mL). The reaction solution was stirred at 70° C. for three hours. The reaction solution was cooled to room temperature. Ethyl acetate and saturated aqueous ammonium chloride were added to the reaction solution, and the organic layer was separated. The organic layer was dried over anhydrous magnesium sulfate, and the insoluble matter was separated by filtration. The filtrate was concentrated and the residue was purified by silica gel column chromatography to obtain the title compound (51 mg).
Workup
- additionwas added to a solution
- temperatureThe reaction solution was cooled to room temperature
- customthe organic layer was separated
- dry with materialThe organic layer was dried over anhydrous magnesium sulfate
- customthe insoluble matter was separated by filtration
- concentrationThe filtrate was concentrated
- customthe residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-5f9f1bdd39544ca494e69e69137b3d71
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08158620B2
Reaction notes
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