Sodium Carbonate → 2-Fluoro-2'-(trifluoromethyl)-3,4'-bipyridine

HRID 473624Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 473624
[F:1][C:2]1[C:7](B(O)O)=[CH:6][CH:5]=[CH:4][N:3]=1.Br[C:12]1[CH:17]=[CH:16][N:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C(O)C.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:1][C:2]1[C:7]([C:12]2[CH:17]=[CH:16][N:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)=[CH:6][CH:5]=[CH:4][N:3]=1

Komponenten

8

Edukt 3

HCID 10340Sodium CarbonateHCID 27832702-Fluoropyridine-3-boronic acidHCID 234369504-Bromo-2-(trifluoromethyl)pyridine

Produkt 1

HCID 593269242-Fluoro-2'-(trifluoromethyl)-3,4'-bipyridine

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel2×HCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

A mixture of 2-fluoropyridin-3-ylboronic acid (0.748 g, 5.3 mmol), 4-bromo-2-(trifluoromethyl)pyridine (1.00 g, 4.4 mmol), Pd(PPh3)2Cl2 (0.155 g, 0.22 mmol) and sodium carbonate (0.797 g, 13.3 mmol) in DME (6.5 mL), ethanol (1.9 mL) and water (0.47 mL) was heated to 95° C. for 2 h. After cooling to room temperature, the mixture was diluted with H2O and extracted with CH2Cl2 (3×). The combined organics were dried over Na2SO4, filtered and concentrated. The residue was purified using column chromatography (EtOAc/Hexanes=0→20%) to give the title compound. MS (ESI, pos. ion) m/z: 243 (M+1).

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with CH2Cl2 (3×)
  3. dry with materialThe combined organics were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified

Quellen und Nachweise

ORD-Eintrag
ord-982a471bee604723b4b7c88e00e160e7
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637500B2

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