Acetic Acid → HCID 23284756, compound

HRID 369212Notes

Reaction equation

HRID 369212 reaction equation
[N:1]([C:4]1[C:13]([Br:14])=[C:12]2[C:7]([C:8](=[O:36])[C:9]([C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:10][N:11]2[C:15]2[CH:20]=[C:19]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:18]([F:29])=[CH:17][C:16]=2[F:30])=[CH:6][C:5]=1[F:37])=[N+]=[N-].C(O)(=O)C.[H][H]>CO.[OH-].[Pd+2].[OH-]>[NH2:1][C:4]1[C:13]([Br:14])=[C:12]2[C:7]([C:8](=[O:36])[C:9]([C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:10][N:11]2[C:15]2[CH:20]=[C:19]([NH:21][C:22]([O:24][C:25]([CH3:27])([CH3:26])[CH3:28])=[O:23])[C:18]([F:29])=[CH:17][C:16]=2[F:30])=[CH:6][C:5]=1[F:37]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 23284655HCID 23284655, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 23284756HCID 23284756, compoundYield 68.1%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

Ethyl 7-azido-8-bromo-1-(5-tert-butoxycarbonylamino-2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate (650 mg) was dissolved in methanol (20 ml). An acetic acid suspension (3 ml) of 20% palladium hydroxide (100 mg) was added to this solution, and the mixture was stirred at room temperature for 3 hours in a hydrogen atmosphere. After palladium hydroxide was removed by filtration, the solvent was distilled off under reduced pressure. The residue was subjected to column chromatography on silica gel (eluent; chloroform) to obtain the title compound (423 mg) as a liver-colored amorphous substance.

Workup

  1. customAfter palladium hydroxide was removed by filtration
  2. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-536935d03ca04f75a76445acd7866d55
Source dataset
uspto-grants-2000_10
Patent number
US06136823

Reaction notes

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