Ethanol → [6-[(4-Chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-3-yl]methylamine

HRID 748844Notes

Reaction equation

HRID 748844 reaction equation
[N:1]([CH2:4][C:5]1[CH:6]=[CH:7][C:8]([CH:11]([S:20]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)(=[O:22])=[O:21])[C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=2[F:19])=[N:9][CH:10]=1)=[N+]=[N-].C(OCC)(=O)C.C(O)C.[H][H]>[Pd].CO.ClCCl>[Cl:29][C:26]1[CH:27]=[CH:28][C:23]([S:20]([CH:11]([C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=2[F:19])[C:8]2[N:9]=[CH:10][C:5]([CH2:4][NH2:1])=[CH:6][CH:7]=2)(=[O:22])=[O:21])=[CH:24][CH:25]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 8857Ethyl AcetateHCID 23114635HCID 23114635, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 23114559[6-[(4-Chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-3-yl]methylamineYield 39%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Under argon atmosphere, 5-azidomethyl-2-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridine (77 mg, 0.177 mmol), palladium on carbon (14 mg), and ethyl acetate (2 ml) were added to ethanol (10 ml). The resulting mixture was stirred for 50 minutes under 1 atom hydrogen atmosphere. After filtration, the filtrate was concentrated under reduced pressure. The residue thus obtained was subjected to chromatography on a silica gel column. A fraction obtained from the elution portion with dichloromethane:methanol=10:1 was concentrated under reduced pressure, whereby the title compound (28 mg, 0.0685 mmol, 39%) was obtained as a white powder.

Workup

  1. filtrationAfter filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue thus obtained

Sources & evidence

ORD record
ord-5475a9e0e5484779b00a33ce4614f1d0
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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