Sodium Carbonate → 2-Chloro-2'-fluoro-3,4'-bipyridine

HRID 911103Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 911103
[F:1][C:2]1[CH:7]=[C:6](I)[CH:5]=[CH:4][N:3]=1.[Cl:9][C:10]1[C:15](B(O)O)=[CH:14][CH:13]=[CH:12][N:11]=1.C([O-])([O-])=O.[Na+].[Na+].P(C(C)(C)C)(C(C)(C)C)C(C)(C)C.[H+].[B-](F)(F)(F)F>CCOC(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2].O.O1CCOCC1>[Cl:9][C:10]1[C:15]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([F:1])[CH:7]=2)=[CH:14][CH:13]=[CH:12][N:11]=1

Komponenten

10

Edukt 5

HCID 10340Sodium CarbonateHCID 28118Tetrafluoroboric acidHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 2762704(2-Chloropyridin-3-yl)boronic acidHCID 70235702-Fluoro-4-iodopyridine

Produkt 1

HCID 161089822-Chloro-2'-fluoro-3,4'-bipyridine

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To 2-fluoro-4-iodopyridine (9.45 g, 42.4 mmol), 2-chloropyridine-3-boronic acid (10.0 g, 63.5 mmol), Na2CO3 (13.5 g, 127 mmol), Pd(OAc)2 (480 mg, 2.12 mmol) and P(tBu)3.HBF4 (1.23 g, 4.24 mmol) was added dioxane (125 mL) and water (45 mL). The mixture was heated overnight at 100° C. in a sealed tube. The resulting mixture was diluted with EtOAc and extracted with water and brine. The organic layer was dried over Na2SO4, filtered and concentrated. The resulting solid was triturated with n-Hexanes and dried to yield 2-chloro-2′-fluoro-[3,4′]bipyridinyl. MS m/z=209 [M+1]+. Calc'd for C10H6ClFN2: 208.62.

Aufarbeitung

  1. extractionextracted with water and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting solid was triturated with n-Hexanes
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-58440308c0a3430e8a495feb6035b8a5
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08022221B2

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