Reaktion #356769

ord-42d232ef5de84170bcdcc8a7f6ebcff4

Reaktionsgleichung

CCOC(=O)c1cncc(Br)c1
ethyl 5-bromonicotinate
OB(O)c1ccccc1-c1ccccc1OCc1ccccc1
{2′-[(phenylmethyl)oxy]-2-biphenylyl}boronic acid
O=C([O-])[O-].[K+].[K+]
potassium carbonate
CCOC(=O)c1cncc(-c2ccccc2-c2ccccc2OCc2ccccc2)c1
colourless gum
Ausbeute 80.6%
CCOC(=O)c1cncc(-c2ccccc2-c2ccccc2OCc2ccccc2)c1
Ethyl 5-{2′-[(phenylmethyl)oxy]-2-biphenylyl}-3-pyridinecarboxylate
Ausbeute 80.6%

Lösungsmittel

Reaktionsbedingungen

Temperatur
90°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    TemperaturAfter cooling the mixture
  2. 2
    Trocknenthe organic phase dried (magnesium sulphate)
  3. 3
    Sonstigeevaporated
  4. 4
    Sonstigechromatographed on silica eluting with ethyl acetate/iso-hexane (1:5)

Vorschrift

A mixture of ethyl 5-bromonicotinate (46 mg, 0.2 mmol), {2′-[(phenylmethyl)oxy]-2-biphenylyl}boronic acid (61 mg, 0.2 mmol), potassium carbonate (221 mg, 1.6 mmol) and tetrakis(triphenylphosphine)palladium(0) (23 mg, 0.02 mmol) was stirred and heated at 90° C. under nitrogen for 2 hours. After cooling the mixture was diluted with ether/water and the organic phase dried (magnesium sulphate), evaporated and chromatographed on silica eluting with ethyl acetate/iso-hexane (1:5) to give 66 mg of colourless gum.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07446222B2uspto-grants-2008_11