2,5-Dibromopyridine → 5-Bromo-3'-fluoro-2,4'-bipyridine

HRID 42022

Reaktionsgleichung

Reaktionsgleichung von HRID 42022
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[F:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][C:15]=1[Sn](CCCC)(CCCC)CCCC>CN(C=O)C.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.[Cu]I>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([C:15]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2[F:9])=[N:3][CH:4]=1

Komponenten

6

Edukt 2

HCID 693532,5-DibromopyridineHCID 222736013-Fluoro-4-(tributylstannyl)pyridine

Produkt 1

HCID 584158125-Bromo-3'-fluoro-2,4'-bipyridineAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

In a schlenck tube, a mixture of 2,5-dibromopyridine (2.11 mmol, 0.500 g), 3-fluoro-4-(tributylstannyl)pyridine (2.32 mmol, 0.896 g), PdCl2(PPh3)2 (0.21 mmol, 0.148 g), CuI (0.43 mmol, 0.080 g) in DMF (5 ml) was heated at 130° C. for 12 hours, under argon atmosphere. The solvent was evaporated and the crude mixture was extracted between water and ethyl acetate. The solid residue was purified by chromatography over SiO2 eluting with DCM/methanol mixtures affording 0.330 g (yield 62%) of the expected product.

Aufarbeitung

  1. customThe solvent was evaporated
  2. extractionthe crude mixture was extracted between water and ethyl acetate
  3. customThe solid residue was purified by chromatography over SiO2 eluting with DCM/methanol

Quellen und Nachweise

ORD-Eintrag
ord-a11cea2e8f2340d298289a02033d0720
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536165B2

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