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

HRID 222753노트

반응식

HRID 222753 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 24593copper(I) bromide촉매HCID 1049Pyridine용매2회

실험 절차

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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-ae8e048f745342b395f5576ab7386999
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207331B2

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