HCID 16739334, compound → HCID 21099424, compound

HRID 1351664Notes

Reaction equation

HRID 1351664 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1/[CH:9]=[CH:10]/[C:11]1[CH:16]=[CH:15][C:14]([S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)(=[O:19])=[O:18])=[CH:13][CH:12]=1>C(OCC)(=O)C.[Pd]>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([S:17]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)(=[O:19])=[O:18])=[CH:13][CH:12]=1

Participants

4

Reactant 1

HCID 16739334HCID 16739334, compound

Product 1

HCID 21099424HCID 21099424, compoundYield 40.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2,4-Difluoro-1-{(E)-2-[4-(phenylsulfonyl)phenyl]vinyl}benzene (Example 51, 57 mg, 0.16 mmol) and palladium (10% wt. on activated carbon, 20 mg) were combined in ethyl acetate (20 mL) and shaken in a Parr apparatus for 2 hours. The catalyst was removed by filtration and the filtrate evaporated in vacuo. The residue was purified by HPLC to yield the title compound as a white solid (23 mg, 40%). δH (400 MHz, CDCl3): 7.93–7.91 (2H, m), 7.84–7.82 (2H, m), 7.56–7.46 (3H, m), 7.27–7.24 (2H, m), 7.00–6.94 (1H, m), 6.76–6.70 (2H, m), 2.92–2.84 (4H, m).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate evaporated in vacuo
  3. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-12526fda66fd4399b9f4f3e4b9e8888d
Source dataset
uspto-grants-2007_05
Patent number
US07217740B2

Reaction notes

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