HCID 21254056, compound → HCID 21254080, compound

HRID 1292387Notes

Reaction equation

HRID 1292387 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([C:18]1[CH:23]=[C:22]([CH3:24])[CH:21]=[C:20]([CH3:25])[CH:19]=1)=[C:12]2[CH2:26][CH2:27][N:28]1[C:36](=[O:37])[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:29]1=[O:38])C1C=CC=CC=1.[H][H]>C(OCC)(=O)C.[Pd]>[CH3:25][C:20]1[CH:19]=[C:18]([C:13]2[NH:14][C:15]3[C:11]([C:12]=2[CH2:26][CH2:27][N:28]2[C:36](=[O:37])[C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[C:29]2=[O:38])=[CH:10][C:9]([OH:8])=[CH:17][CH:16]=3)[CH:23]=[C:22]([CH3:24])[CH:21]=1

Participants

5

Reactant 2

HCID 21254056HCID 21254056, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21254080HCID 21254080, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 2-[2-[5-benzyloxy-2-(3,5-dimethylphenyl)-1H-indol-3-yl]ethyl]isoindole-1,3-dione (510 mg in 20 mL dry ethyl acetate was added 197 mg of 10% palladium on carbon catalyst. The reaction flask was fitted with a hydrogen balloon, evacuated and recharged with hydrogen (3 times) and stirred at room temperature. After 37 hours the reaction was flushed with nitrogen, filtered over diatomaceous earth and concentrated in vacuo to provide the crude title compound (418 mg).

Workup

  1. customevacuated
  2. customAfter 37 hours the reaction was flushed with nitrogen
  3. filtrationfiltered over diatomaceous earth
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-105816a60d854e229a437d458b81769f
Source dataset
uspto-grants-1998_05
Patent number
US05756507

Reaction notes

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