Water → (E)-8-(pyridin-4-yl)-2-(2-(quinolin-2-yl)vinyl)isoquinolin-1(2H)-one

HRID 920934노트

반응식

HRID 920934 반응식
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:8]=[CH:9][CH:10]=[C:11]3[C:16]=2[C:15](=[O:17])[NH:14][CH:13]=[CH:12]3)=[CH:3][CH:2]=1.Br/[CH:19]=[CH:20]/[C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:22]=1.O.CC(=O)OCC>CN(C=O)C>[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:8]=[CH:9][CH:10]=[C:11]3[C:16]=2[C:15](=[O:17])[N:14](/[CH:19]=[CH:20]/[C:21]2[CH:30]=[CH:29][C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[N:22]=2)[CH:13]=[CH:12]3)=[CH:3][CH:2]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 10421517(E)-2-(2-bromovinyl)quinolineHCID 866831488-(Pyridin-4-yl)isoquinolin-1(2H)-one

생성물 1

HCID 86683149(E)-8-(pyridin-4-yl)-2-(2-(quinolin-2-yl)vinyl)isoquinolin-1(2H)-one수율 40%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
115 °C

실험 절차

8-(Pyridin-4-yl)isoquinolin-1(2H)-one (40 mg, 0.180 mmol) and (E)-2-(2-bromovinyl)quinoline (50.6 mg, 0.216 mmol) were dissolved in 2 mL of DMF under argon. The reaction mixture was stirred for 10 h at 115° C. Then, water and EA were added. The organic phase was washed with water and brine, dried (MgSO4) and concentrated. The crude product was purified by chromatography (CombiFlash, normal phase, gradient elution, using 3-5% DCM in methanol) to yield the title compound as yellow solid (27 mg, 40.0%). LCMS: 376.1; Rt=1.497.

후처리

  1. washThe organic phase was washed with water and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customThe crude product was purified by chromatography (CombiFlash, normal phase, gradient elution, using 3-5% DCM in methanol)

출처 및 근거

ORD 기록
ord-19c5bff4ea0d4e87810c584cba59c5a2
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09273068B2

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