HCID 69208222, compound → HCID 20636419, compound

HRID 2252844Notes

Reaction equation

HRID 2252844 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([CH:9]=[CH:10][CH2:11][NH:12][C:13](=[O:21])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2I)=[CH:5][CH:4]=1>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C.C([O-])(=O)C.C([O-])(=O)C.[Pd+2]>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([CH2:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13](=[O:21])[NH:12][CH:11]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 1

HCID 69208222HCID 69208222, compound

Product 1

HCID 20636419HCID 20636419, compound

Reagents, catalysts & solvents 3

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

Under a N2 atmosphere, 2.04 g (5.17 mmol) of an (E/Z) mixture of 2-iodo-benzoic acid-[3-(6-methoxy-pyridin-3-yl)-allylamide], 1.53 g (5.17 mmol) of tetra-butylammonium chloride and 22 mg (0.1 mmol) of palladium diacetate are dissolved in 80 ml of DMF, then 1.8 ml (12.9 mmol) of trethylamine are added and stirring effected for 2 days at 110° C. Filtration is carried out, and the DMF is partially evaporated on a RE. The residue is dissolved with EtOAc and diluted Na2CO3 solution, the water phase separated and extraction effected twice more with EtOAc. The organic phases are washed twice with water and brine, dried (Na2SO4) and concentrated by evaporation. Column chromatography (SiO2, methylene chloride/acetone 3:1), concentration by evaporation and stirring in petroleum ether yield 4-[(6-methoxy-pyridin-3-yl)-methyl]-2H-isoquinolin-1-one; m.p. 191° C.; HPLC(gradient20-100) tRef=13.0.

Workup

  1. addition1.8 ml (12.9 mmol) of trethylamine are added
  2. filtrationFiltration
  3. customthe DMF is partially evaporated on a RE
  4. dissolutionThe residue is dissolved with EtOAc and diluted Na2CO3 solution
  5. customthe water phase separated
  6. extractionextraction
  7. washThe organic phases are washed twice with water and brine
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated by evaporation
  10. concentrationColumn chromatography (SiO2, methylene chloride/acetone 3:1), concentration
  11. customby evaporation
  12. stirringstirring in petroleum ether

Sources & evidence

ORD record
ord-7243c64ca26f4dc8b0d5bed5135d284f
Source dataset
uspto-grants-2008_01
Patent number
US07323474B2

Reaction notes

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