Hydrochloric Acid → 4-(5-Chloro-2-hydroxyphenyl)pyridine-2-carbonitrile

HRID 46330

Reaktionsgleichung

Reaktionsgleichung von HRID 46330
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6](B(O)O)[CH:7]=1.Cl[C:13]1[CH:18]=[CH:17][N:16]=[C:15]([C:19]#[N:20])[CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+].Cl>O1CCOCC1.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([C:13]2[CH:18]=[CH:17][N:16]=[C:15]([C:19]#[N:20])[CH:14]=2)[CH:7]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 6933424-Chloro-2-pyridinecarbonitrileHCID 23005362(5-Chloro-2-hydroxyphenyl)boronic Acid (contains varying amounts of Anhydride)

Produkt 1

HCID 1360636254-(5-Chloro-2-hydroxyphenyl)pyridine-2-carbonitrileAusbeute 8,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

(5-Chloro-2-hydroxyphenyl)boronic acid (2.0 g, 0.012 mol), 4-chloropyridine-2-carbonitrile (1.61 g, 0.012 mol), (1,1′-bis(diphenylphosphino)ferrocene)dichloropalladium(II) (0.424 g, 0.00058 mol) and sodium carbonate (3.7 g, 0.035 mol) in 1,4-dioxane (20.0 mL) and deionised water (1.0 mL) were degassed with nitrogen (×3) before heating at 100° C. for 18 hours under nitrogen. The reaction was cooled and hydrochloric acid (2.0 M aqueous solution, 30.0 mL) added. Reaction was filtered, washing with ethyl acetate (50.0 mL). The organic layer was concentrated in vacuo and purified by flash column chromatography on the ISCO™ (40 g SiO2) eluting with ethyl acetate:heptane (gradient 0:1 to 7:3, by volume) to afford the title compound as a yellow solid, 0.23 g, 8.6% yield.

Aufarbeitung

  1. temperatureThe reaction was cooled
  2. customReaction
  3. filtrationwas filtered
  4. washwashing with ethyl acetate (50.0 mL)
  5. concentrationThe organic layer was concentrated in vacuo
  6. custompurified by flash column chromatography on the ISCO™ (40 g SiO2)
  7. washeluting with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-6274da3e6fdd4badbbf2fa3c0e80ad14
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541588B2

Verknüpfte Notizen

Wird geladen…