Sodium Carbonate → HCID 21109697, Verbindung

HRID 1159215Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1159215
Br[C:2]1[C:3]([O:9][CH2:10][CH2:11][CH2:12][CH3:13])=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1.[F:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][C:16]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[CH2:10]([O:9][C:3]1[C:2]([C:16]2[CH:17]=[C:18]([C:21]([F:23])([F:24])[F:22])[CH:19]=[CH:20][C:15]=2[F:14])=[CH:7][C:6]([CH3:8])=[CH:5][N:4]=1)[CH2:11][CH2:12][CH3:13]

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 27633012-Fluoro-5-(trifluoromethyl)phenylboronic acidHCID 21109699HCID 21109699, Verbindung

Produkt 1

HCID 21109697HCID 21109697, VerbindungAusbeute 77,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

3-Bromo-2-butoxy-5-methyl-pyridine (0.96 g, 3.9 mmol) was dissolved in toluene (6 mL). To this solution was added [2-fluoro-5-(trifluoromethyl)phenyl]-boronic acid (1.2 g, 5.9 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloro-methane complex (161 mg), and 2 N sodium carbonate solution (5.9 mL). The whole mixture was heated with stirring at 90° C. for 18 h, cooled to room temperature and eluted with ethyl acetate over 10 g ChemElut (Varian). The solvent was evaporated and the residue was purified by column chromatography on silica (n-heptane/ethyl acetate gradient) to yield 0.99 g of the title compound as a yellow oil, MS (ISP) 328.3 (M+H)+.

Aufarbeitung

  1. temperatureThe whole mixture was heated
  2. temperaturecooled to room temperature
  3. washeluted with ethyl acetate over 10 g ChemElut (Varian)
  4. customThe solvent was evaporated
  5. customthe residue was purified by column chromatography on silica (n-heptane/ethyl acetate gradient)

Quellen und Nachweise

ORD-Eintrag
ord-6fdae0e2fa4c4489bae04e2e825656a7
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07812028B2

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