Potassium Carbonate → 2-[4-(5-chloro-3-fluoropyridin-2-yloxy)phenoxy]propionic acid N-cyano-N-methylamide
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([F:16])[C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)=[N:6][CH:7]=1.[C:17]([N:19]([CH3:25])[C:20](=[O:24])[CH:21](Br)[CH3:22])#[N:18].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.[I-].[K+]>[C:17]([N:19]([CH3:25])[C:20](=[O:24])[CH:21]([O:15][C:12]1[CH:11]=[CH:10][C:9]([O:8][C:5]2[C:4]([F:16])=[CH:3][C:2]([Cl:1])=[CH:7][N:6]=2)=[CH:14][CH:13]=1)[CH3:22])#[N:18]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
48.0 g (0.20 mole) of 4-(5-chloro-3-fluoropyridin-2-yloxy)phenol and 38.2 g (0.20 mole) of 2-bromopropionic acid N-cyano-N-methylamide are dissolved in 400 ml of acetonitrile. 35.9 g (0.26 mole) of potassium carbonate and 0.33 g (0.002 mole) of potassium iodide are added to the solution and the reaction mixture is heated for 13 hours at 80° C. The precipitate is removed by filtration, the filtrate is concentrated by evaporation and the residue is taken up in 500 ml of methlyene chloride. The solution is purified by treatment with activated carbon and filtration through silica gel. The filtrate is concentrated by evaporation and the residue is crystallised from a mixture of hexane and ethyl acetate, affording 61 g of 2-[4-(5-chloro-3-fluoropyridin-2-yloxy)phenoxy]propionic acid N-cyano-N-methylamide.
Workup
- customThe precipitate is removed by filtration
- concentrationthe filtrate is concentrated by evaporation
- filtrationThe solution is purified by treatment with activated carbon and filtration through silica gel
- concentrationThe filtrate is concentrated by evaporation
- customthe residue is crystallised from a mixture of hexane and ethyl acetate
Sources & evidence
- ORD record
- ord-fc15e6acc0a44fef85849122ee436e2f
- Source dataset
- uspto-grants-1988_07
- Patent number
- US04759796
Reaction notes
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