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

HRID 920934Notes

Reaction equation

HRID 920934 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
115 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-19c5bff4ea0d4e87810c584cba59c5a2
Source dataset
uspto-grants-2016_03
Patent number
US09273068B2

Reaction notes

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