Hexane → HCID 23114641, compound

HRID 2080515Notes

Reaction equation

HRID 2080515 reaction equation
[Cl:1][C:2]1[C:3]([CH:14]([C:28]2[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:29]=2[F:35])[S:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=2)(=[O:17])=[O:16])=[CH:4][C:5](/[CH:8]=[CH:9]/[C:10]([O:12][CH3:13])=[O:11])=[N:6][CH:7]=1.CCCCCC>C(OCC)(=O)C.CO.[C].[Pd]>[Cl:1][C:2]1[C:3]([CH:14]([C:28]2[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:29]=2[F:35])[S:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:25])([F:27])[F:26])=[CH:20][CH:19]=2)(=[O:17])=[O:16])=[CH:4][C:5]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[N:6][CH:7]=1

Participants

6

Reactant 2

HCID 8058HexaneHCID 58734257HCID 58734257, compound

Product 1

HCID 23114641HCID 23114641, compoundYield 85.7%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a mixed solvent of ethyl acetate (3 ml) and methanol (3 ml) was dissolved methyl(E)-3-[5-chloro-4-[(2,5-difluorophenyl)(4-trifluoromethylphenylsulfonyl)methyl]pyridin-2-yl]acrylate (110 mg, 0.21 mmol). To the resulting solution was added 10% palladium-carbon catalyst (60 mg). Under a hydrogen atmosphere, the resulting mixture was stirred at room temperature for 2 hours. After the catalyst was removed by Celite filtration, the filtrate was concentrated under reduced pressure. The residue thus obtained was subjected to flash silica gel column chromatography. The fraction obtained from the hexane:ethyl acetate=4:1 eluate was concentrated under reduced pressure to give the title compound (94 mg, 0.18 mmol, 85%) as a white solid.

Workup

  1. customAfter the catalyst was removed by Celite filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue thus obtained
  4. concentrationethyl acetate=4:1 eluate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9e6fb38d5cca457fab1a0b08435eb2e3
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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