Ethyl Acetate → HCID 18002680, compound

HRID 478703Notes

Reaction equation

HRID 478703 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8](OS(C(F)(F)F)(=O)=O)=[CH:9][CH:10]=2)[CH:5]=[C:4]([CH3:20])[N:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OCC)(=O)C.[CH3:46][N:47]1CCCC1=O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.[C-]#N.[Zn+2].[C-]#N>[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:46]#[N:47])=[CH:9][CH:10]=2)[CH:5]=[C:4]([CH3:20])[N:3]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11776TriphenylphosphineHCID 13387N-methyl-2-pyrrolidoneHCID 85802609HCID 85802609, compound

Product 1

HCID 18002680HCID 18002680, compound

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 167845palladium(II) acetateCatalyst

Procedure

Palladium acetate (0.28 g) was added to a heated mixture of trifluoro-methanesulfonic acid 1-amino-3-methylisoquinolin-6-yl ester (1.9 g), zinc cyanide (0.74 g) and triphenylphosphine (0.33 g) in 24 mL of N-methyl-pyrrolidone at 190° C. (exothermic!). Stirring was continued at 190° C. for 2 h After cooling to room temperature, ethyl acetate was added and the organic mixture washed with 2N aqueous ammonia, water and brine and dried (magnesium sulfate). Filtration and concentration afforded a brownish oil, which was purified by silica chromatography (dichloromethane/methanol=98/2) to give 0.68 g of the title compound. ESI-MS: 184 (MH+).

Workup

  1. washthe organic mixture washed with 2N aqueous ammonia, water and brine
  2. dry with materialdried (magnesium sulfate)
  3. filtrationFiltration and concentration
  4. customafforded a brownish oil, which
  5. customwas purified by silica chromatography (dichloromethane/methanol=98/2)

Sources & evidence

ORD record
ord-5893de7c9da7449cb15baa95e857e48a
Source dataset
uspto-grants-2003_11
Patent number
US06642253B2

Reaction notes

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