Water → 5-Azidomethyl-2-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridine

HRID 748843Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 748843
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]([C:20]2[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=2[F:27])[C:12]2[CH:17]=[CH:16][C:15]([CH2:18]O)=[CH:14][N:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[N-:28]=[N+:29]=[N-:30].[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C(Cl)(Cl)(Cl)Cl.CN(C)C=O.C(OCC)(=O)C.CCCCCC>[N:28]([CH2:18][C:15]1[CH:16]=[CH:17][C:12]([CH:11]([S:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)(=[O:10])=[O:9])[C:20]2[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=2[F:27])=[N:13][CH:14]=1)=[N+:29]=[N-:30]

Komponenten

9

Edukt 4

HCID 962WaterHCID 11776TriphenylphosphineHCID 33557Sodium AzideHCID 230285882-[(4-Chlorophenylsulfonyl)-(2,5-difluorophenyl)methyl]-5-(hydroxymethyl)pyridine

Produkt 1

HCID 231146355-Azidomethyl-2-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridineAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 5943Carbon TetrachlorideLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8058HexaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

In a mixture of carbon tetrachloride (4 ml) and N,N-dimethylformamide (16 ml) was dissolved the 2-[(4-chlorophenylsulfonyl) (2,5-difluorophenyl)methyl]-5-(hydroxymethyl)pyridine (471 mg, 1.15 mmol) obtained in Example 331. Sodium azide (112 mg, 1.72 mmol) and triphenylphosphine (451 mg, 1.72 mmol) were added and the mixture was stirred at 90° C. for 3 hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was then washed successively with water and brine, dried over sodium sulfate and 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 hexane:ethyl acetate=3:1 was concentrated under reduced pressure, whereby the title compound (244 mg, 0.561 mmol, 49%) was obtained as a colorless amorphous substance.

Aufarbeitung

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was then washed successively with water and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue thus obtained

Quellen und Nachweise

ORD-Eintrag
ord-6836e3ba3df342e8bea4f002f9d7ddd4
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07399775B2

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