HCID 54028665, compound → HCID 22627191, compound

HRID 1108713Notes

Reaction equation

HRID 1108713 reaction equation
[CH3:1][O:2][C:3]([CH:5]=[CH:6][C:7]1[C:15]2[C:10](=[CH:11][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:13][CH:14]=2)[NH:9][CH:8]=1)=[O:4]>O1CCOCC1.CO.[Pd]>[CH3:1][O:2][C:3]([CH2:5][CH2:6][C:7]1[C:15]2[C:10](=[CH:11][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:13][CH:14]=2)[NH:9][CH:8]=1)=[O:4]

Participants

5

Reactant 1

HCID 54028665HCID 54028665, compound

Product 1

HCID 22627191HCID 22627191, compoundYield 82.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of methyl 3-(2-methoxycarbonylethenyl)indole-6-carboxylate (213 mg) in a mixture of 1,4-dioxane (2 ml) and methanol (3 ml) was added 10% palladium on carbon (40 mg) and the mixture was stirred under hydrogen at 20° C. for 6.5 hours. The resulting mixture was filtered through celite and the filtrate was evaporated in vacuo. The residue was triturated with diisopropyl ether to give methyl 3-(2-methoxycarbonylethyl)indole-6-carboxylate (177 mg).

Workup

  1. filtrationThe resulting mixture was filtered through celite
  2. customthe filtrate was evaporated in vacuo
  3. customThe residue was triturated with diisopropyl ether

Sources & evidence

ORD record
ord-9b36d7afef574179a2b08f1579ac1291
Source dataset
uspto-grants-2000_05
Patent number
US06069156

Reaction notes

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