Cesium carbonate → 4'-tert-Butoxycarbonylamino-2'-methyl-biphenyl-3-carboxylic acid

HRID 1678457Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1678457
[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[CH:12][C:11](Br)=[C:10]([CH3:15])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[C:17]([C:20]1[CH:21]=[C:22](B(O)O)[CH:23]=[CH:24][CH:25]=1)([OH:19])=[O:18].C(=O)([O-])[O-].[Cs+].[Cs+]>COCCOC>[C:1]([O:5][C:6]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:24]2[CH:23]=[CH:22][CH:21]=[C:20]([C:17]([OH:19])=[O:18])[CH:25]=2)=[C:10]([CH3:15])[CH:9]=1)=[O:16])([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 27339573-Carboxyphenylboronic acidHCID 59822380N-BOC-4-bromo-3-methylaniline

Produkt 1

HCID 598223634'-tert-Butoxycarbonylamino-2'-methyl-biphenyl-3-carboxylic acidAusbeute 89,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

A mixture of (4-bromo-3-methyl-phenyl)-carbamic acid tert-butyl ester (765 mg), 3-carboxyphenyl boronic acid (446 mg), cesium carbonate (875 mg) and tetrakis(triphenylphosphine)palladium0 (catalytic quantity), in 1:2 aqueous DME (30 ml) was heated to reflux for 18 h. The mixture was then allowed to cool and was then partitioned between 1M HCl and dichloromethane. The dried extracts were then evaporated giving the title compound as a pale brown foam (785 mg).

Aufarbeitung

  1. temperatureto reflux for 18 h
  2. temperatureto cool
  3. customwas then partitioned between 1M HCl and dichloromethane
  4. customThe dried extracts were then evaporated

Quellen und Nachweise

ORD-Eintrag
ord-57bcc5bc08944f70bf4583b13aa6c929
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08008303B2

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