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

HRID 920934ノート

反応式

HRID 920934 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
115 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-19c5bff4ea0d4e87810c584cba59c5a2
出典データセット
uspto-grants-2016_03
特許番号
US09273068B2

反応ノート

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