HCID 18368154, compound → HCID 18367865, compound

HRID 379857Notes

Reaction equation

HRID 379857 reaction equation
[C:1]([NH:4][C:5]1[C:13]2[C:8](=[CH:9][C:10]([N+:14]([O-])=O)=[CH:11][CH:12]=2)[NH:7][C:6]=1[C:17](=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=[O:3])[CH3:2]>[Pd].C(O)C>[C:1]([NH:4][C:5]1[C:13]2[C:8](=[CH:9][C:10]([NH2:14])=[CH:11][CH:12]=2)[NH:7][C:6]=1[C:17](=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 18368154HCID 18368154, compound

Product 1

HCID 18367865HCID 18367865, compoundYield 51.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3-Acetylamino-2-benzoyl-6-nitroindole (Example 152, 180 mg. 0.56 mmol) was hydrogenolyzed in the presence of palladium on activated carbon (5%, 18 mg) in ethanol (30 ml) at atmospheric pressure for 4 h. Catalyst was removed by filtration and the filtrate was concentrated. The residue was purified by flash column chromatography eluting with 0 to 50% ethyl acetate in hexanes and the product recrystallized from a mixture of methanol/ethyl acetate/hexane to give 85 mg of the title compound. m.p.: 219-221° C. 1H-NMR (DMSO-d6) δ: 10.9 (1H, br s), 9.54 (1H, s), 7.44-7.66 (5H, m), 7.38(1H, d, J=9.2 Hz), 6.47-6.45 (2H, m), 5.35 (2H, s), 1.69 (3H, s)

Workup

  1. customCatalyst was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by flash column chromatography
  4. washeluting with 0 to 50% ethyl acetate in hexanes
  5. customthe product recrystallized from a mixture of methanol/ethyl acetate/hexane

Sources & evidence

ORD record
ord-e0eb65e4ac1f4910b21c5dd1f16e75c5
Source dataset
uspto-grants-2001_10
Patent number
US06300363B1

Reaction notes

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