反応式
[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]参加物
実験手順
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. 1 H-NMR (CDCl3) δ: 10.41 (1H, br.s), 9.02 (1H, d, J=9.2 Hz), 8.55-8.52 (1H, m), 8.42-8.38 (1H, m), 7.79-7.65 (2H, m), 7.05 (1H, dd, J=6.6, 4.8 Hz), 7.00 (1H, d, J=9.2 Hz).
後処理
- 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
出典と根拠
- ORDレコード
- ord-d6fbe6a2092e442292e0c8ac58d31ead
- 出典データセット
- uspto-grants-2004_03
- 特許番号
- US06713482B2
関連ノート
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