HCID 58734272, compound → HCID 23114628, compound

HRID 2080508Notes

Reaction equation

HRID 2080508 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]([C:25]2[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=2[F:32])[C:12]2[C:17]([F:18])=[CH:16][N:15]=[C:14](/[CH:19]=[CH:20]/[C:21]([O:23][CH3:24])=[O:22])[CH:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1>C(O)C.O1CCOCC1.ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]([C:25]2[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=2[F:32])[C:12]2[C:17]([F:18])=[CH:16][N:15]=[C:14]([CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])[CH:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 58734272HCID 58734272, compound

Product 1

HCID 23114628HCID 23114628, compoundYield 87%

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 (1 ml) was added to a solution of methyl(E)-3-[4-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]-5-fluoropyridin-2-yl]acrylate (290 mg, 0.602 mmol) in a mixture of ethanol (6 ml) and 1,4-dioxane (4 ml). The resulting mixture was stirred vigorously for 30 minutes under a hydrogen atmosphere of 1 atmospheric pressure. The reaction mixture was filtered, followed by concentration under reduced pressure. The residue thus obtained was dissolved in dichloromethane. The resulting solution was dried over magnesium sulfate and concentrated under reduced pressure. The residue thus obtained was washed with hexane to give the title compound (252 mg, 0.521 mmol, 87%) 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. filtrationThe reaction mixture was filtered
  4. concentrationfollowed by concentration under reduced pressure
  5. customThe residue thus obtained
  6. dry with materialThe resulting solution was dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue thus obtained
  9. washwas washed with hexane

Sources & evidence

ORD record
ord-1d54c6295d5941649846553654d98f2e
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

Loading…