Cesium carbonate → HCID 117770781, compound
Reaction equation
FC(F)(F)C(O)=O.[OH:8][C:9]1[N:16]=[CH:15][C:14]([C:17]2[CH:21]=[CH:20][N:19]([CH3:22])[N:18]=2)=[C:13]([O:23][CH3:24])[C:10]=1[C:11]#[N:12].F[C:26]1[N:33]=[CH:32][CH:31]=[CH:30][C:27]=1[C:28]#[N:29].C(=O)([O-])[O-].[Cs+].[Cs+].C(=O)([O-])O.[Na+]>CN(C)C=O>[CH3:24][O:23][C:13]1[C:14]([C:17]2[CH:21]=[CH:20][N:19]([CH3:22])[N:18]=2)=[CH:15][N:16]([C:26]2[C:27]([C:28]#[N:29])=[CH:30][CH:31]=[CH:32][N:33]=2)[C:9](=[O:8])[C:10]=1[C:11]#[N:12]Participants
Procedure
A mixture of 2-hydroxy-4-methoxy-5-(1-methyl-1H-pyrazol-3-yl)nicotinonitrile trifluoroacetate obtained in Step D (0.20 g), 2-fluoronicotinonitrile (0.710 g), cesium carbonate (0.45 g) and N,N-dimethylformamide (30 mL) was stirred at room temperature for 16 hr. The reaction mixture was slowly poured into saturated sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. To the residue was added a mixed solvent (2 mL) of isopropyl ether/ethyl acetate=1/2, and the mixture was stirred for 15 min. The precipitate was collected by filtration to give the title compound (0.12 g).
Workup
- extractionthe mixture was extracted with ethyl acetate
- washThe extract was washed with saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- customthe solvent was evaporated under reduced pressure
- additionTo the residue was added a mixed solvent (2 mL) of isopropyl ether/ethyl acetate=1/2
- stirringthe mixture was stirred for 15 min
- filtrationThe precipitate was collected by filtration
Sources & evidence
- ORD record
- ord-5feaf8fdc66b4d12b15e091e108a02de
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09085578B2
Reaction notes
Loading…