HCID 58734236, compound → HCID 23114758, compound

HRID 2080513Notes

Reaction equation

HRID 2080513 reaction equation
[Cl:1][C:2]1[C:3]([CH:14]([S:23]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=2)(=[O:25])=[O:24])[C:15]2[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=2[F:22])=[CH:4][C:5](/[CH:8]=[CH:9]/[C:10]([O:12][CH3:13])=[O:11])=[N:6][CH:7]=1>C(O)C.O1CCOCC1.ClCCl>[Cl:1][C:2]1[C:3]([CH:14]([S:23]([C:26]2[CH:27]=[CH:28][C:29]([Cl:32])=[CH:30][CH:31]=2)(=[O:25])=[O:24])[C:15]2[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=2[F:22])=[CH:4][C:5]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[N:6][CH:7]=1

Participants

5

Reactant 1

HCID 58734236HCID 58734236, compound

Product 1

HCID 23114758HCID 23114758, compoundYield 93%

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent2×HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A Raney nickel suspension (“R-100”, product of Nikko Rika Corporation) was washed sequentially with water and ethanol to give a corresponding ethanol suspension. The resulting ethanol suspension (2 ml) was added to a solution of methyl(E)-3-[5-chloro-4-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-2-yl]acrylate (770 mg, 1.55 mmol) in a mixture of ethanol (10 ml) and 1,4-dioxane (5 ml). Under a hydrogen atmosphere of 1 atmospheric pressure, the resulting mixture was stirred vigorously for 30 minutes. After the reaction mixture was filtered, the filtrate was concentrated under reduced pressure. The residue thus obtained was dissolved in dichloromethane (15 ml). The resulting solution was dried over magnesium sulfate, and concentrated under reduced pressure to give the title compound (720 mg, 1.44 mmol, 93%) as a white powder.

Workup

  1. washA Raney nickel suspension (“R-100”, product of Nikko Rika Corporation) was washed sequentially with water and ethanol
  2. customto give a corresponding ethanol suspension
  3. filtrationAfter the reaction mixture was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue thus obtained
  6. dry with materialThe resulting solution was dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bd2d153dc8a44ff4bcfca563cc1be88e
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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