HCID 15485021, compound → HCID 15485025, compound

HRID 1936205Notes

Reaction equation

HRID 1936205 reaction equation
Br[C:2]1[C:7]([F:8])=[C:6]([F:9])[C:5]([F:10])=[C:4]([S:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)(=[O:13])=[O:12])[C:3]=1[F:23]>CO.[Pd].C>[F:10][C:5]1[C:6]([F:9])=[C:7]([F:8])[CH:2]=[C:3]([F:23])[C:4]=1[S:11]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)(=[O:12])=[O:13]

Participants

4

Reactant 1

HCID 15485021HCID 15485021, compound

Product 1

HCID 15485025HCID 15485025, compoundYield 40.8%

Reagents, catalysts & solvents 2

HCID 14818447PalladiumcarbonCatalystHCID 887MethanolSolvent

Procedure

1-Bromo-2,4,5,6-tetrafluoro-3-[(4-methoxyphenyl)aminosulfonyl]benzene (250 mg, 0.6 mmol) (Example 5) was dissolved in methanol (25 ml) and placed in a closed vessel. A catalytic amount of 10% Pd/charcoal (25 mg) was added and the mixture was hydrogenated at 60 psi H2 for 4 h. The mixture was filtered through celite, the solvent was evaporated and the residue was purified by chromatography (silica; EtOAc/Hexane, 1:4) to yield 82 mg of the title compound. 1H-NMR (CDCl3): δ 7.10 (2H, dd, J=9.0 and 2.0 Hz), 6.94 (1H, br s), 6.85 (1H, m), 6.79 (2H, dd, J=9.0 and 2.0 Hz), 3.75 (3H, s). MS(EI): 335 (20, M+), 122 (100). Anal. Calcd. for C13H9F4NO3S: C, 46.57; H, 2.71; N, 4.18; S, 9.56. Found: C, 46.46; H, 2.67; N, 4.17; S, 9.52.

Workup

  1. customplaced in a closed vessel
  2. filtrationThe 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-9f891e6026374a61bb265883cb23a065
Source dataset
uspto-grants-2002_05
Patent number
US06388131B2

Reaction notes

Loading…