Sodium hydride → 2-[(3-Cyclobutyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)oxy]benzonitrile

HRID 645888ノート

反応式

HRID 645888 の反応式
[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

6

反応物 3

HCID 24758Sodium hydrideHCID 27593582-IodobenzonitrileHCID 100820813-Cyclobutyl-2,3,4,5-tetrahydro-1H-benzo[D]azepin-7-OL

生成物 1

HCID 103585162-[(3-Cyclobutyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)oxy]benzonitrile収率 41%

試薬・触媒・溶媒 2

HCID 24593copper(I) bromide触媒HCID 1049Pyridine溶媒2 回

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

  1. temperaturecooled in an ice bath
  2. temperaturethe mixture heated
  3. temperatureunder reflux for 2.5 hours
  4. temperatureto cool to room temperature
  5. customthe solvent removed in vacuo
  6. customThe resulting residue was purified by column chromatography
  7. washeluting with a mixture of ammonia:methanol:dichloromethane (0.2:1.8:98)

出典と根拠

ORDレコード
ord-5dbb7058c3e3452ba5ffe73d199d4d6c
出典データセット
uspto-grants-2010_04
特許番号
US07704994B2

反応ノート

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