HCID 67101589, compound → HCID 23114666, compound

HRID 748834Notes

Reaction equation

HRID 748834 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]([C:24]2[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=2[F:31])[C:12]2[N:17]=[CH:16][C:15]([CH:18]=[CH:19][C:20]([O:22][CH3:23])=[O:21])=[CH:14][CH:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[H][H]>C(O)C.[Pd]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]([C:24]2[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=2[F:31])[C:12]2[N:17]=[CH:16][C:15]([CH2:18][CH2:19][C:20]([O:22][CH3:23])=[O:21])=[CH:14][CH:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 67101589HCID 67101589, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 23114666HCID 23114666, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Methyl 3-[6-[(4-chlorophenylsulfonyl)-(2,5-difluorophenyl)methyl]pyridin-3-yl]acrylate (160 mg, 0.34 mmol) was dissolved in ethanol (15 ml). Palladium on carbon (30 mg) was added and the resulting mixture was vigorously stirred under 1 atm hydrogen atmosphere for 24 hours. The reaction mixture was filtered and then, concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane:ethyl acetate=5:1), whereby the title compound (94 mg, 58%) was obtained as needle crystals.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by silica gel chromatography (hexane:ethyl acetate=5:1), whereby the title compound (94 mg, 58%)
  4. customwas obtained as needle crystals

Sources & evidence

ORD record
ord-375b711730ab4de9ab25966b2e1c2aa2
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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