Water → HCID 24958100, compound

HRID 2196597Notes

Reaction equation

HRID 2196597 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([C:6]([NH:8][CH2:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=3)[N:13]=[CH:12][CH:11]=2)=[O:7])=[C:4]([CH:26]=[CH2:27])[CH:3]=1.C([O-])(=O)C.[Na+].O>CS(C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:24][CH:25]=1)[C:6](=[O:7])[N:8]([CH2:9][C:10]1[C:19]3[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=3)[N:13]=[CH:12][CH:11]=1)[CH:27]=[CH:26]2

Participants

6

Reactant 3

HCID 962WaterHCID 517045Sodium AcetateHCID 68993440HCID 68993440, compound

Product 1

HCID 24958100HCID 24958100, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

4-Chloro-N-((6,7-dimethoxyquinolin-4-yl)methyl)-2-vinylbenzamide (0.084 g, 0.22 mmol), sodium acetate (0.036 g, 0.44 mmol), and palladium acetate (0.002 g, 0.011 mmol) were combined in DMSO (5 ml). The reaction mixture was stirred under an oxygen balloon at 100° C. overnight. The mixture was poured into water and extracted with ethyl acetate three times. The combined organic layers were washed with water and brine, dried over sodium sulfate, filtered and concentrated. The crude material was purified by prep-TLC plate with ethyl acetate to give 6-chloro-2-((6,7-dimethoxyquinolin-4-yl)methyl)isoquinolin-1(2H)-one. MS (ESI, pos. ion) m/z: 381 (M+1). 1H NMR (CDCl3): 4.03 (6H, s), 4.80 (1H, d), 5.95 (1H, d), 5.40 (2H, s), 7.05 (1H, d), 7.40 (1H, s), 7.56 (2H, m), 7.70 (1H, s), 7.87 (1H, d), 8.64 (1H, d).

Workup

  1. extractionextracted with ethyl acetate three times
  2. washThe combined organic layers were washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified by prep-TLC plate with ethyl acetate

Sources & evidence

ORD record
ord-673520d7b3c8453eb196d39b6553d597
Source dataset
uspto-grants-2012_12
Patent number
US08338455B2

Reaction notes

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