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

HRID 41908

반응식

HRID 41908 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)[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

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 346812,6-DibromotolueneHCID 574241426-(Dimethylamino)-1,2-dihydroisoquinolin-1-one

생성물 1

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

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
150 °C

실험 절차

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)+.

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 (30% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-0a63f4c45f3a441b9729adefaf9bae1a
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536166B2

연결된 노트

불러오는 중…