HCID 18368135, compound → HCID 18368034, compound

HRID 379750Notes

Reaction equation

HRID 379750 reaction equation
[C:1]([NH:4][C:5]1[C:13]2[C:8](=[CH:9][C:10]([Cl:14])=[CH:11][CH:12]=2)[NH:7][C:6]=1[C:15](=[O:30])[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22]CC2C=CC=CC=2)[CH:17]=1)(=[O:3])[CH3:2]>[Pd].C(OCC)(=O)C.C(O)C>[C:1]([NH:4][C:5]1[C:13]2[C:8](=[CH:9][C:10]([Cl:14])=[CH:11][CH:12]=2)[NH:7][C:6]=1[C:15](=[O:30])[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([OH:22])[CH:17]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 1

HCID 18368135HCID 18368135, compound

Product 1

HCID 18368034HCID 18368034, compoundYield 40%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Acetylamino-2-(3-benzyloxybenzoyl)-6-chloroindole (Example 44, 0.42 g, 1.0 mmol) was hydrogenolyzed in the presence of palladium on activated carbon (10%, 0.10 g) in a mixture of ethyl acetate (10 ml) and ethanol (1.0 ml) at atmospheric pressure overnight. The mixture was filtered and the filtrate was concentrated in vacuo. The residual solid was recrystallization from ethyl acetate/hexane to afford 0.13 g (40%) of the title compound as a pale yellow solid. m.p.: 130-145° C. 1H-NMR (CDCl3) δ: 11.73 (1H, brs), 9.80-9.65 (2H, m), 7.62 (1H, d, J=8.4 Hz), 7.50-6.98 (5H, m), 1.76 (3H, s) The signal due to H of OH was not observed.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customrecrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-699c203e867f4d39a95f87750bf91979
Source dataset
uspto-grants-2001_10
Patent number
US06300363B1

Reaction notes

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