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

HRID 2080401Notes

Reaction equation

HRID 2080401 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]>[C].[Pd].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

7

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 2

HCID 178418390HCID 178418390, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

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

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customThe residue thus obtained
  4. concentrationmethanol=10:1 eluate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-735ac8b49aa0423bb8e61706655135fb
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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