Sodium hydride → 2-[(3-Cyclobutyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)oxy]benzonitrile
反応式
[CH:1]1([N:5]2[CH2:11][CH2:10][C:9]3[CH:12]=[C:13]([OH:16])[CH:14]=[CH:15][C:8]=3[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.[H-].[Na+].I[C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[C:22]#[N:23]>N1C=CC=CC=1.[Cu]Br>[CH:1]1([N:5]2[CH2:6][CH2:7][C:8]3[CH:15]=[CH:14][C:13]([O:16][C:20]4[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=4[C:22]#[N:23])=[CH:12][C:9]=3[CH2:10][CH2:11]2)[CH2:4][CH2:3][CH2:2]1参加物
実験手順
3-Cyclobutyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ol (E3) (300 mg, 1.38 mmol) was dissolved in pyridine (10 ml), cooled in an ice bath and treated with sodium hydride (60% in mineral oil) (66 mg, 1.66 mmol) under argon. The resulting mixture was stirred for 5 minutes, treated with copper (I) bromide (277 mg, 1.93 mmol) and allowed to warm to room temperature over 30 minutes. A solution of 2-iodobenzonitrile (948 mg, 4.14 mmol) in pyridine (2 ml) was added and the mixture heated under reflux for 2.5 hours. The mixture was allowed to cool to room temperature and the solvent removed in vacuo. The resulting residue was purified by column chromatography eluting with a mixture of ammonia:methanol:dichloromethane (0.2:1.8:98) to afford the title compound (180 mg); MS (ES+) m/e 319 [M+H]+.
後処理
- temperaturecooled in an ice bath
- temperaturethe mixture heated
- temperatureunder reflux for 2.5 hours
- temperatureto cool to room temperature
- customthe solvent removed in vacuo
- customThe resulting residue was purified by column chromatography
- washeluting with a mixture of ammonia:methanol:dichloromethane (0.2:1.8:98)
出典と根拠
- ORDレコード
- ord-ae8e048f745342b395f5576ab7386999
- 出典データセット
- uspto-grants-2012_06
- 特許番号
- US08207331B2
反応ノート
読み込み中…