Dichloromethane → HCID 58127393, Verbindung

HRID 1963821Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1963821
FC(F)(F)S(O[C:7]1[C:12]([F:13])=[CH:11][CH:10]=[C:9]([F:14])[N:8]=1)(=O)=O.[Cl:17][C:18]1[C:19](B(O)O)=[CH:20][C:21]([F:24])=[N:22][CH:23]=1.C(=O)([O-])[O-].[Na+].[Na+].C(Cl)Cl>C1COCC1.CCOC(C)=O.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:17][C:18]1[C:19]([C:7]2[C:12]([F:13])=[CH:11][CH:10]=[C:9]([F:14])[N:8]=2)=[CH:20][C:21]([F:24])=[N:22][CH:23]=1

Komponenten

9

Edukt 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 44754822(5-Chloro-2-fluoropyridin-4-yl)boronic acidHCID 86650604Methanesulfonic acid, 1,1,1-trifluoro-, 3,6-difluoro-2-pyridinyl ester

Produkt 1

HCID 58127393HCID 58127393, VerbindungAusbeute 85,5 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 3,6-difluoropyridin-2-yl trifluoromethanesulfonate (3.50 g, 13.30 mmol) and 5-chloro-2-fluoropyridine-4-boronic acid (3.27 g, 18.62 mmol) in THF (27 ml) was degassed by bubbling Argon gas for 10 min. Aqueous sodium carbonate (13.30 ml, 26.6 mmol) and PdCl2(dppf).CH2Cl2 adduct (0.652 g, 0.798 mmol)were added, and the mixture was degassed for an additional 5 min. The resulting reaction mixture was stirred at about 100° C. for 2 hr in a sealed vessel. The reaction mixture was cooled to ambient temperature, diluted with EtOAc and water. The separated organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. The resulting residue was purified by column chromatography over silica gel (heptanes/ethyl acetate gradient) to yield 2.78 g (85% yield) of 5′-chloro-2′,3,6-trifluoro-2,4′-bipyridine as a crystalline solid. LCMS (m/z): 244.9 [M+H]+; retention time=0.86 min.

Aufarbeitung

  1. customwas degassed
  2. customby bubbling Argon gas for 10 min
  3. customthe mixture was degassed for an additional 5 min
  4. customThe resulting reaction mixture
  5. temperatureThe reaction mixture was cooled to ambient temperature
  6. dry with materialThe separated organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe resulting residue was purified by column chromatography over silica gel (heptanes/ethyl acetate gradient)

Quellen und Nachweise

ORD-Eintrag
ord-342df9738c304193900732f9dee68a54
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08415381B2

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