Sodium Carbonate → {5-[2-Chloro-4-(ethylsulfonyl)phenoxy]biphenyl-3-yl}acetic acid

HRID 1686467Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1686467
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.[C:25]1(B(O)O)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.Cl.[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:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:7]=1

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 57791934{3-Bromo-5-[2-chloro-4-(ethylsulfonyl)phenoxy]phenyl}acetic acid

Produkt 1

HCID 57791961{5-[2-Chloro-4-(ethylsulfonyl)phenoxy]biphenyl-3-yl}acetic acidAusbeute 51,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178506420bis(diphenylphosphino)ferrocene palladium(II)KatalysatorHCID 313Hydrochloric AcidLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

The product from example 55 step (vi) (0.45 g), phenyl boronic acid (0.190 g), sodium carbonate (0.44 g) and bisdiphenylphosphinoferrocene palladium (II) (0.04 g) in dry dioxane (20 ml) were heated to 80° C. for 20 h. Mixture diluted with 2M HCl, extracted with ethyl acetate, dried (MgSO4) and evaporated under reduced pressure to an oil, which was purified by RPHPLC to give a cream solid (0.23 g).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  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-4262f872e4b94e8fa0d6b1204d141ddf
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08148572B2

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