Cesium carbonate → 5-(5-Chloropyridin-2-yl)-2,3-difluoropyridine

HRID 219277Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 219277
Br[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[F:15][C:16]1[C:21]([F:22])=[CH:20][C:19](B2OC(C)(C)C(C)(C)O2)=[CH:18][N:17]=1>O1CCOCC1.O>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([C:19]2[CH:20]=[C:21]([F:22])[C:16]([F:15])=[N:17][CH:18]=2)=[N:3][CH:4]=1

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 8170982-Bromo-5-chloropyridineHCID 533983942,3-Difluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Produkt 1

HCID 580155045-(5-Chloropyridin-2-yl)-2,3-difluoropyridineAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a pressure vessel was added 2-bromo-5-chloropyridine (3.0 g, 16 mmol), cesium carbonate (15 g, 47 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium(ii) dichloride dichloromethane complex (2.5 g, 3.1 mmol), and 2,3-difluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (4.5 g, 19 mmol) in 1,4-dioxane (120 mL) and water (22 mL). The mixture was flushed with argon, sealed and stirred at 90° C. for three hours. The mixture was concentrated, diluted with dichloromethane and washed with water. Organic extracts were concentrated and purified by MPLC (eluted with 0-10% methanol in dichloromethane) to yield 5-(5-chloropyridin-2-yl)-2,3-difluoropyridine as a yellow solid (2.4 g, 68%). MS m/z=227.2 [M+1]+. Calc'd for C10H5ClF2N2: 226.6.

Aufarbeitung

  1. customThe mixture was flushed with argon
  2. customsealed
  3. concentrationThe mixture was concentrated
  4. additiondiluted with dichloromethane
  5. washwashed with water
  6. concentrationOrganic extracts were concentrated
  7. custompurified by MPLC (eluted with 0-10% methanol in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-c476fa2be4e1426985ea097a6e796db4
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08198448B2

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