Triethylamine → HCID 20636419, compound

HRID 49225Notes

Reaction equation

HRID 49225 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.C(N(CC)CC)C>[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

6

Reactant 2

HCID 8471TriethylamineHCID 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 triethylamine 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) tRet=7.9.

Workup

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

Sources & evidence

ORD record
ord-4cc805ad0b3141739d58882b4f759965
Source dataset
uspto-grants-2004_03
Patent number
US06706731B2

Reaction notes

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