HCID 15550636, compound → HCID 12016878, compound

HRID 2228434Notes

Reaction equation

HRID 2228434 reaction equation
Br[C:2]1[C:7]([F:8])=[C:6]([F:9])[C:5]([F:10])=[C:4]([F:11])[C:3]=1[S:12]([NH:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([OH:24])[CH:17]=1)(=[O:14])=[O:13]>CO.[Pd].C>[F:11][C:4]1[C:5]([F:10])=[C:6]([F:9])[C:7]([F:8])=[CH:2][C:3]=1[S:12]([NH:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([OH:24])[CH:17]=1)(=[O:14])=[O:13]

Participants

4

Reactant 1

HCID 15550636HCID 15550636, compound

Product 1

HCID 12016878HCID 12016878, compound

Reagents, catalysts & solvents 2

HCID 14818447PalladiumcarbonCatalystHCID 887MethanolSolvent

Procedure

The title compound was prepared via catalytic hydrogenation of the compound prepared in Example F above. Briefly, the starting material was in methanol and placed in a closed vessel. A catalytic amount of 10% Pd/charcoal was added and the mixture was hydrogenated at 60 psi H2 for 4 h. The resulting mixture was filtered through celite, the solvent was evaporated and the residue was purified by chromatography (silica; EtOAc/Hexane, 1:4) to yield the title compound. 1H-NMR (CDCl3): δ 7.43 (1H, m), 6.80 (1H, br s), 6.73-6.60 (3H, m), 5.67 (1H, s), 3.84 (3H, s). MS(EI): 351 (20, M+), 138 (100). Anal. Calcd. for C13H9F4NO4S: C, 44.45; H, 2.58; N, 3.99; S, 9.13. Found: C, 44.39; H, 2.59; N, 3.94; S, 9.24.

Workup

  1. customplaced in a closed vessel
  2. filtrationThe resulting mixture was filtered through celite
  3. customthe solvent was evaporated
  4. customthe residue was purified by chromatography (silica; EtOAc/Hexane, 1:4)

Sources & evidence

ORD record
ord-76ce787084e14b48bd7d4625a101c560
Source dataset
uspto-grants-2002_07
Patent number
US06417176B2

Reaction notes

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