Toluene → 4-(5-Chloro-2-methoxyphenyl)pyridazine

HRID 1619625

Reaktionsgleichung

Reaktionsgleichung von HRID 1619625
C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+].Br.Br[C:16]1[CH:21]=[CH:20][N:19]=[N:18][CH:17]=1.[Cl:22][C:23]1[CH:24]=[CH:25][C:26]([O:32][CH3:33])=[C:27](B(O)O)[CH:28]=1>[Pd].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.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.C(O)C>[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([O:32][CH3:33])=[C:25]([C:16]2[CH:21]=[CH:20][N:19]=[N:18][CH:17]=2)[CH:24]=1

Komponenten

7

Edukt 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 27357515-Chloro-2-methoxyphenylboronic acidHCID 534079064-Bromopyridazine hydrobromide

Produkt 1

HCID 580422674-(5-Chloro-2-methoxyphenyl)pyridazineAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To an argon purged flask containing toluene (187 mL), ethanol (20.6 mL) and a 2M aqueous solution of sodium carbonate (132.3 mL) was added 4-bromopyridazine hydrobromide (Preparation 5, 15 g, 64 mmol), 5-chloro-2-methoxybenzeneboronic acid (13.4 g, 72 mmol) and tetrakis(triphenylphosphine) palladium (0) (3.2 g, 2.8 mmol). The flask was purged with argon again, then the reaction mixture heated to 110° C. for 4 hours. The mixture was filtered through Celite™ and the filtrate concentrated in vacuo. The residue was partitioned between ethyl acetate and water. The organic layer was washed with water and brine, then dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The crude residue was dissolved in ethyl acetate and extracted with a 2M aqueous solution of hydrogen chloride (×3). The aqueous layer was basified with sodium hydrogen carbonate and extracted with ethyl acetate. The organic layer was then washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to afford the title compound (8 g, 58%).

Aufarbeitung

  1. customThe flask was purged with argon again
  2. filtrationThe mixture was filtered through Celite™
  3. concentrationthe filtrate concentrated in vacuo
  4. customThe residue was partitioned between ethyl acetate and water
  5. washThe organic layer was washed with water and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. dissolutionThe crude residue was dissolved in ethyl acetate
  10. extractionextracted with a 2M aqueous solution of hydrogen chloride (×3)
  11. extractionextracted with ethyl acetate
  12. washThe organic layer was then washed with water and brine
  13. dry with materialdried over anhydrous sodium sulfate
  14. filtrationfiltered
  15. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b5fd5bf0c9cb498c85a9ce89b94337ca
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772293B2

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