Potassium Carbonate → 2-(3-Bromo-2-methyl-phenyl)-6-dimethylamino-2H-isoquinolin-1-one

HRID 2069751

反応式

HRID 2069751 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)[C:23]=1[CH3:29]>CS(C)=O>[Br:21][C:22]1[C:23]([CH3:29])=[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 11430Potassium CarbonateHCID 346812,6-DibromotolueneHCID 574241426-(Dimethylamino)-1,2-dihydroisoquinolin-1-one

生成物 1

HCID 592165052-(3-Bromo-2-methyl-phenyl)-6-dimethylamino-2H-isoquinolin-1-one収率 44.4%

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 (50 mg, 0.27 mmol), cuprous iodide (10 mg, 0.053 mmol), and potassium carbonate (37 mg, 0.27 mmol) were deposited in sealed vessel. 3 mL DMSO and 2,6-dibromotoluene (133 mg, 0.532 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 (30% ethyl acetate/hexanes) to yield 2-(3-Bromo-2-methyl-phenyl)-6-dimethylamino-2H-isoquinolin-1-one (43 mg, 0.12 mmol). MS (ESI) 357 (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 (30% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-6c8ecd7061f348bf8365e466179f082d
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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