Ethanol → 6-(3-Butyl-5-methyl-isoxazol-4-ylmethoxy)-pyridazine-3-carboxylic acid ethyl ester

HRID 1958075Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1958075
[CH2:1]([C:5]1[C:9]([CH2:10][O:11][C:12]2[N:13]=[N:14][C:15](Cl)=[CH:16][CH:17]=2)=[C:8]([CH3:19])[O:7][N:6]=1)[CH2:2][CH2:3][CH3:4].[C:20](=[O:23])([O-])[O-:21].[Na+].[Na+].[CH2:26](O)[CH3:27]>C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:26]([O:21][C:20]([C:15]1[N:14]=[N:13][C:12]([O:11][CH2:10][C:9]2[C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[N:6][O:7][C:8]=2[CH3:19])=[CH:17][CH:16]=1)=[O:23])[CH3:27]

Komponenten

6

Edukt 3

HCID 702EthanolHCID 10340Sodium CarbonateHCID 86647344HCID 86647344, Verbindung

Produkt 1

HCID 666439586-(3-Butyl-5-methyl-isoxazol-4-ylmethoxy)-pyridazine-3-carboxylic acid ethyl esterAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)Katalysator

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A suspension of 3-(3-butyl-5-methyl-isoxazol-4-ylmethoxy)-6-chloro-pyridazine (1.2 g, 3.6 mmol) and sodium carbonate (379 mg, 3.6 mmol) in ethanol (20 mL) was evacuated and filled with argon five times. 1,1′-Bis(diphenylphosphino)ferrocene (198 mg, 3.6 mmol) and palladium(II) acetate (80 mg, 0.36 mmol) were added then the flask was evacuated again and filled with carbon monoxide. The reaction mixture was then heated to 50° C. After 15 h the reaction mixture was cooled, filtered through decalite and evaporated. The residue was purified by chromatography (silica, 0 to 50% ethyl acetate in heptane) to give the title compound (1.0 g, 88%) as a light yellow oil. MS: m/e=320.2 [M+H]+.

Aufarbeitung

  1. customwas evacuated
  2. additionfilled with argon five times
  3. customthe flask was evacuated again
  4. additionfilled with carbon monoxide
  5. temperatureAfter 15 h the reaction mixture was cooled
  6. filtrationfiltered through decalite
  7. customevaporated
  8. customThe residue was purified by chromatography (silica, 0 to 50% ethyl acetate in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-0b3fdf0604c04c9b856d069e84307171
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08410104B2

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