Sodium Carbonate → 2-(5-Chloro-2-fluorophenyl)pyridin-4-amine

HRID 1522547Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1522547
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:11])=[C:6](B(O)O)[CH:7]=1.Cl[C:13]1[CH:18]=[C:17]([NH2:19])[CH:16]=[CH:15][N:14]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:11])=[C:6]([C:13]2[CH:18]=[C:17]([NH2:19])[CH:16]=[CH:15][N:14]=2)[CH:7]=1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 844322-Chloropyridin-4-amineHCID 3718925(5-Chloro-2-fluoro-phenyl)boronic acid

Produkt 1

HCID 674696072-(5-Chloro-2-fluorophenyl)pyridin-4-amineAusbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

5-Chloro-2-fluorophenylboronic acid (2.7 g, 15.48 mmol), 2-chloropyridin-4-amine (1.531 g, 11.91 mmol), sodium carbonate (5.96 ml, 11.91 mmol), and bis(triphenylphosphine) palladium chloride (0.836 g, 1.191 mmol) were combined in dioxane (54 mL) and refluxed for 3 hours. The reaction was cooled, the solvent removed in vacuo and the reaction mixture partitioned between brine and EtOAc. The organic layer was separated, dried over MgSO4 filtered and purified using NH silica column chromatography and a gradient of 5-95% EtOAc in hexanes to afford the title compound as a white solid (522 mg; 20%). ESI-MS: m/z 223.1 (M+H).

Aufarbeitung

  1. temperaturerefluxed for 3 hours
  2. temperatureThe reaction was cooled
  3. customthe solvent removed in vacuo
  4. customthe reaction mixture partitioned between brine and EtOAc
  5. customThe organic layer was separated
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. custompurified

Quellen und Nachweise

ORD-Eintrag
ord-a58b868b655f4f409c464457c1063e99
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073918B2

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