Hexane → HCID 23114787, compound

HRID 2080446Notes

Reaction equation

HRID 2080446 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]([C:26]2[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:27]=2[F:33])[C:12]2[CH:17]=[CH:16][CH:15]=[C:14](/[CH:18]=[CH:19]/[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=3)[N:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.CCCCCC.C(OCC)(=O)C>C(O)C.O1CCOCC1.[Ni]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]([C:26]2[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:27]=2[F:33])[C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=3)[N:13]=2)(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 23114544HCID 23114544, compound

Product 1

HCID 23114787HCID 23114787, compoundYield 61%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To a mixed solution of (E)-2-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]-6-(2-pyridin-2-ylvinyl)pyridine (180 mg, 0.373 mmol) in ethanol (5 ml) and 1,4-dioxane (2 ml) was added an ethanol suspension (1 ml) of Raney nickel. Under a hydrogen atmosphere of 1 atmospheric pressure, the resulting mixture was vigorously stirred for 1.5 hours. After filtration of the reaction mixture, 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=3:2 eluate was concentrated under reduced pressure, followed by recrystallization from hexane:ethyl acetate to give the title compound (110 mg, 0.227 mmol, 61%) as a white powder.

Workup

  1. filtrationAfter filtration of the reaction mixture
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue thus obtained
  4. concentrationethyl acetate=3:2 eluate was concentrated under reduced pressure
  5. customfollowed by recrystallization from hexane

Sources & evidence

ORD record
ord-46b4aa6e2b9242e6b796f85471fbacff
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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