{3-Bromo-5-[2-chloro-4-(ethylsulfonyl)phenoxy]phenyl}acetic acid → {3-[2-Chloro-4-(ethylsulfonyl)phenoxy]-5-pyridin-2-ylphenyl}acetic acid

HRID 1686468Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1686468
Br[C:2]1[CH:3]=[C:4]([CH2:21][C:22]([OH:24])=[O:23])[CH:5]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH2:18][CH3:19])(=[O:17])=[O:16])=[CH:11][C:10]=2[Cl:20])[CH:7]=1.[Br-].[N:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[Zn+]>O1CCOCC1.O.[Pd+2].C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[Cl:20][C:10]1[CH:11]=[C:12]([S:15]([CH2:18][CH3:19])(=[O:17])=[O:16])[CH:13]=[CH:14][C:9]=1[O:8][C:6]1[CH:5]=[C:4]([CH2:21][C:22]([OH:24])=[O:23])[CH:3]=[C:2]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][N:26]=2)[CH:7]=1

Komponenten

6

Edukt 2

HCID 57791934{3-Bromo-5-[2-chloro-4-(ethylsulfonyl)phenoxy]phenyl}acetic acidHCID 178418723HCID 178418723, Verbindung

Produkt 1

HCID 16123987{3-[2-Chloro-4-(ethylsulfonyl)phenoxy]-5-pyridin-2-ylphenyl}acetic acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178506420bis(diphenylphosphino)ferrocene palladium(II)KatalysatorHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

The product from example 55 step (vi) (0.45 g), 2-pyridyl zinc bromide (0.89 ml) and bisdiphenylphosphinoferrocene palladium (II) (0.04 g) in dry dioxane (20 ml) were heated to 90° C. for 20 h. Mixture diluted with water, extracted with DCM, dried (MgSO4) and evaporated under reduced pressure to an oil, which was purified by RPHPLC to give a white solid (3 mg).

Aufarbeitung

  1. extractionextracted with DCM
  2. dry with materialdried (MgSO4)
  3. customevaporated under reduced pressure to an oil, which
  4. customwas purified by RPHPLC

Quellen und Nachweise

ORD-Eintrag
ord-d32e2f03e6a04392b263bcea98b6adad
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08148572B2

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