Methyl Acrylate → Methyl 3-(2-(methoxycarbonyl)vinyl)-4,7-dimethylindole-2-carboxylate

HRID 361625Notes

Reaction equation

HRID 361625 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]2[C:3]=1[CH:4]=[C:5]([C:12]([O:14][CH3:15])=[O:13])[NH:6]2.[C:16]([O:20][CH3:21])(=[O:19])[CH:17]=[CH2:18]>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:21][O:20][C:16]([CH:17]=[CH:18][C:4]1[C:3]2[C:7](=[C:8]([CH3:11])[CH:9]=[CH:10][C:2]=2[CH3:1])[NH:6][C:5]=1[C:12]([O:14][CH3:15])=[O:13])=[O:19]

Participants

5

Reactant 2

HCID 7294Methyl AcrylateHCID 4714976methyl 4,7-dimethyl-1H-indole-2-carboxylate

Product 1

HCID 54299854Methyl 3-(2-(methoxycarbonyl)vinyl)-4,7-dimethylindole-2-carboxylateYield 48%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent2×

Conditions

Temperature
0 °C

Procedure

In 23 ml of anhydrous acetonitrile were dissolved 1.5 g (7.4 mmol) of methyl 4,7-dimethylindole-2-carboxylate and 7.6 ml of methyl acrylate. The air in the reaction system was substituted with nitrogen. After cooling the reaction mixture to 0° C., 1.66 g (7.4 mmol) of palladium acetate was added and the reaction mixture was stirred for 30 minutes. Stirring was further continued at room temperature for 19 hours. After addition of 60 ml of acetonitrile, the reaction mixture was subjected to Celite filtration. The filtrate was concentrated under reduced pressure and the solids thus obtained were purified by silica gel column chromatography to provide 680 mg of yellow crystals. Yield: 48%

Workup

  1. stirringStirring
  2. waitwas further continued at room temperature for 19 hours
  3. filtrationthe reaction mixture was subjected to Celite filtration
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe solids thus obtained
  6. customwere purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4cbc9c815bee405e9040df728c41b8a5
Source dataset
uspto-grants-1999_02
Patent number
US05866594

Reaction notes

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