Ethanol → Methyl 3-[6-(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl-5-fluoropyridin-3-yl]propionate

HRID 2080433Notes

Reaction equation

HRID 2080433 reaction equation
C(O)C.[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([C:14]2[N:19]=[C:18]([CH2:20][C:21]3[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=3[F:28])[C:17]([CH:29]=[CH:30][C:31]([O:33][CH3:34])=[O:32])=[CH:16][C:15]=2[F:35])(=[O:13])=[O:12])=[CH:7][CH:6]=1>ClCCl>[Cl:4][C:5]1[CH:6]=[CH:7][C:8]([S:11]([C:14]2[N:19]=[C:18]([CH2:20][C:21]3[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=3[F:28])[C:17]([CH2:29][CH2:30][C:31]([O:33][CH3:34])=[O:32])=[CH:16][C:15]=2[F:35])(=[O:12])=[O:13])=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 67101326HCID 67101326, compound

Product 1

HCID 23114759Methyl 3-[6-(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl-5-fluoropyridin-3-yl]propionateYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A Raney nickel suspension (“R-100”, product of Nikko Rica Corporation) (1 ml) was washed sequentially with water and ethanol to give an ethanol (10 ml) suspension. The resulting suspension was added to an ethanol (40 ml) solution of methyl 3-[6-(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl-5-fluoropyridin-3-yl]acrylate (1.38 g, 2.86 mmol). Under a hydrogen atmosphere, the resulting mixture was stirred at room temperature for 1 hour. The reaction mixture was filtered through Celite and the filtrate was concentrated under reduced pressure. The residue thus obtained was dissolved in dichloromethane. The resulting solution was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to give the title compound 1.37 g, 2.83 mmol, 99%) as a white solid.

Workup

  1. washA Raney nickel suspension (“R-100”, product of Nikko Rica Corporation) (1 ml) was washed sequentially with water and ethanol
  2. customto give an ethanol (10 ml) suspension
  3. filtrationThe reaction mixture was filtered through Celite
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue thus obtained
  6. dry with materialThe resulting solution was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9acd0113027c4f55a8ba8e11a538fa16
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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