反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH:6]=[C:5]2[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:20][CH3:21])[CH:14]=1.F[B-](F)(F)F.[CH3:27][O+](C)C.[OH-].[Na+]>ClC(Cl)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([O:12][CH3:27])[CH:6]=[C:5]2[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:20][CH3:21])[CH:14]=1参加物
5
実験手順
To a suspension of 6-bromo-4-(3-ethoxy-phenyl)-1H-quinolin-2-one (7.4 g, 21.5 mmol) in 60 ml dichloroethane was added trimethyloxonium tetrafluoroborate (BF4OMe3, 3.66 g, 24.7 mmol). The resulting mixture was stirred at ambient temperature overnight. After cooling to 0° C., was added 60 ml of 10% aqueous NaOH dropwise. The reaction mixture was stirred for another six hours at ambient temperature. It was then partitioned between dichloromethane and water. The organic layer was washed brine, dried over MgSO4, filtered and concentrated under vacuum to give an off-white solid. The solid was chromatographed on flash silica gel eluting with dichoromethane to yield the titled compound of 23A as a white solid (4.48 g, 58% yield).
後処理
- temperatureAfter cooling to 0° C.
- stirringThe reaction mixture was stirred for another six hours at ambient temperature
- customIt was then partitioned between dichloromethane and water
- washThe organic layer was washed brine
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated under vacuum
- customto give an off-white solid
- customThe solid was chromatographed on flash silica gel eluting with dichoromethane
出典と根拠
- ORDレコード
- ord-8cb0a23cb9cb4214a6753163d2276bc8
- 出典データセット
- uspto-grants-2004_03
- 特許番号
- US06710209B2
関連ノート
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