1,3-Dibromobenzene → HCID 59216430, 화합물

HRID 2069744

반응식

HRID 2069744 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 59216430HCID 59216430, 화합물수율 61.9%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
150 °C

실험 절차

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)−.

후처리

  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)

출처 및 근거

ORD 기록
ord-bd46e15f052346c892daece9c9f2f2ea
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08299077B2

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