HCID 18368181, compound → HCID 18368172, compound

HRID 379863Notes

Reaction equation

HRID 379863 reaction equation
[C:1]([C:9]1[NH:10][C:11]2[C:16]([C:17]=1[NH:18][C:19](=[O:31])[CH2:20][CH:21]([O:23]CC1C=CC=CC=1)[CH3:22])=[CH:15][CH:14]=[C:13]([Cl:32])[CH:12]=2)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(OCC)(=O)C.[Pd]>[C:1]([C:9]1[NH:10][C:11]2[C:16]([C:17]=1[NH:18][C:19](=[O:31])[CH2:20][CH:21]([OH:23])[CH3:22])=[CH:15][CH:14]=[C:13]([Cl:32])[CH:12]=2)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 18368181HCID 18368181, compound

Product 1

HCID 18368172HCID 18368172, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-benzoyl-3-(3-benzyloxybutyrylamino)-6-chloroindole (Step 1) (2.3 g, 5.1 mmol) and 10% Pd—C (0.2 g) in ethyl acetate (50 ml) was stirred at room temperature for 24 h under a hydrogen atmosphere. The mixture was filtered through a pad of Celite and the filtrate was concentrated. Purification by flash column chromatography eluting with hexane/ethyl acetate (1/1) gave a yellow amorphous solid. Recrystallization from ethyl acetate/hexane afforded 290 mg (16%) of the titled compound as a pale yellow solid. m.p.: 159-162° C.

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. concentrationthe filtrate was concentrated
  3. customPurification by flash column chromatography
  4. washeluting with hexane/ethyl acetate (1/1)
  5. customgave a yellow amorphous solid
  6. customRecrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-ee6d06ac879f4bfa8fca004472820b80
Source dataset
uspto-grants-2001_10
Patent number
US06300363B1

Reaction notes

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