1,3-Dibromobenzene → HCID 59216430、化合物

HRID 2069744

反応式

HRID 2069744 の反応式
[CH3:1][N:2]([CH3:14])[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[NH:8][CH:7]=[CH:6]2.C(=O)([O-])[O-].[K+].[K+].[Br:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24](Br)[CH:23]=1>CS(C)=O>[Br:21][C:22]1[CH:23]=[C:24]([N:8]2[CH:7]=[CH:6][C:5]3[C:10](=[CH:11][CH:12]=[C:3]([N:2]([CH3:14])[CH3:1])[CH:4]=3)[C:9]2=[O:13])[CH:25]=[CH:26][CH:27]=1

参加物

5

反応物 3

HCID 79271,3-DibromobenzeneHCID 11430Potassium CarbonateHCID 574241426-(Dimethylamino)-1,2-dihydroisoquinolin-1-one

生成物 1

HCID 59216430HCID 59216430、化合物収率 61.9%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
150 °C

実験手順

6-Dimethylamino-2H-isoquinolin-1-one (39 mg, 0.21 mmol), cuprous iodide (8.0 mg, 0.041 mmol), and potassium carbonate (29 mg, 0.21 mmol) were deposited in sealed vessel. 3 mL DMSO and 1,3-dibromobenzene (98 mg, 0.42 mmol) were added. Argon was bubbled through the mixture for 2 minutes and the lid was tightly closed. This was heated at 150° C. for 5 hours. The resulting mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, concentrated in vacuo, and purified by flash chromatography (25% ethyl acetate/hexanes) to yield 2-(3-Bromo-phenyl)-6-dimethylamino-2H-isoquinolin-1-one (45 mg, 0.13 mmol). MS (ESI) 345.0 (M+H)−.

後処理

  1. customArgon was bubbled through the mixture for 2 minutes
  2. customthe lid was tightly closed
  3. customThe resulting mixture was partitioned between ethyl acetate and water
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. custompurified by flash chromatography (25% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-bd46e15f052346c892daece9c9f2f2ea
出典データセット
uspto-grants-2012_10
特許番号
US08299077B2

関連ノート

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