Water → 5-(3-methoxyphenyl)-2-(3-pyridylmethyl)-1H-isoindole-1,3 (2H)-dione

HRID 1609591Notes

Reaction equation

HRID 1609591 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([Mg]Br)[CH:6]=[CH:7][CH:8]=1.[N:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][N:18]2[C:26](=[O:27])[C:25]3[C:20](=[CH:21][CH:22]=[C:23](OS(C(F)(F)F)(=O)=O)[CH:24]=3)[C:19]2=[O:36])[CH:12]=1.O.C(OCC)(=O)C>O1CCCC1.[Cl-].[Zn+2].[Cl-].C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:23]2[CH:24]=[C:25]3[C:20](=[CH:21][CH:22]=2)[C:19](=[O:36])[N:18]([CH2:17][C:13]2[CH:12]=[N:11][CH:16]=[CH:15][CH:14]=2)[C:26]3=[O:27])[CH:6]=[CH:7][CH:8]=1

Participants

9

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 57242191HCID 57242191, compoundHCID 178490745HCID 178490745, compound

Product 1

HCID 572694995-(3-methoxyphenyl)-2-(3-pyridylmethyl)-1H-isoindole-1,3 (2H)-dione

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 3007855ZincchlorideCatalystHCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of 1.80 g of zinc chloride in 8.8 ml of tetrahydrofuran was added 8.8 ml of tetrahydrofuran solution (1.0M) of 3-methoxyphenylmagnesium bromide, and the resultant mixture was stirred at room temperature for 20 minutes. This solution was added to a mixture of 2.27 g of 2-(3-pyridylmethyl)-5-(trifluoromethanesulfonyloxy)-1H-isoindole-1,3 (2H)-dione, 27 mg of palladium acetate, 131 mg of 1,1'-bis(diphenylphosphino)ferrocene and 18 ml of tetrahydrofuran and stirred at room temperature for 17 hours. After finishing the reaction, the mixture was mixed with water under ice cooling and shaken with ethyl acetate. The organic layer was washed with water and saturated brine in order, dried over anhydrous magnesium sulfate and concentrated in vacuo. The resultant residue was chromatographed on a column of silica gel, eluting with ethyl acetate and hexane (1:3) to (1:1) to give 1.71 g of the titled compound.

Workup

  1. customthe reaction
  2. washThe organic layer was washed with water and saturated brine in order
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe resultant residue was chromatographed on a column of silica gel
  6. washeluting with ethyl acetate and hexane (1:3) to (1:1)

Sources & evidence

ORD record
ord-287d6ec62c274948a4327c70de94552e
Source dataset
uspto-grants-1995_03
Patent number
US05401756

Reaction notes

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