Reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[CH:9][C:7]=1[NH2:8])([O-:5])=[O:4].F[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1>CC(N(C)C)=O>[N+:3]([C:6]1[CH:12]=[C:11]([C:13]([F:14])([F:15])[F:16])[CH:10]=[CH:9][C:7]=1[NH:8][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)([O-:5])=[O:4]Participants
Procedure
To a stirred suspension of sodium hydride (2.40 g, 60 mmol) in dimethylacetamide (60 ml) at room temperature under a nitrogen atmosphere was added a solution of 2-nitro-4-trifluoromethylaniline (10.31 g, 50 mmol) in dimethylacetamide (20 ml) during 30 min. After stirring the mixture at room temperature for 15 min., a solution of 2-fluoropyridine (5.83 g, 60 mmol) in dimethylacetamide (20 ml) was added during 5 min. The resulting mixture was heated to reflux for about 8 h. Volatiles were removed by evaporation under reduced pressure. The residue was dissolved into ethyl acetate (200 ml) and washed with water (3×100 ml). The organic layer was dried (magnesium sulfate) and concentrated to dryness. Column chromatography (silica gel, 250 g; n-hexane/ethyl acetate (17/3)) yielded 3.38 g (23%) of the titled compound as yellow solids.
Workup
- temperatureThe resulting mixture was heated
- temperatureto reflux for about 8 h
- customVolatiles were removed by evaporation under reduced pressure
- dissolutionThe residue was dissolved into ethyl acetate (200 ml)
- washwashed with water (3×100 ml)
- dry with materialThe organic layer was dried (magnesium sulfate)
- concentrationconcentrated to dryness
Sources & evidence
- ORD record
- ord-15ac6d17175a4c66a1c9ddce6e6c5ca2
- Source dataset
- uspto-grants-2001_10
- Patent number
- US06310079B1
Linked notes
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