Potassium Carbonate → 1-(cyclopropylmethyl)-5-methoxy-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one

HRID 1747813Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1747813
Cl[C:2]1[C:7](=[O:8])[C:6]([O:9][CH3:10])=[CH:5][N:4]([CH2:11][CH:12]2[CH2:14][CH2:13]2)[N:3]=1.[C:15]1([N:21]2[C:25](B3OC(C)(C)C(C)(C)O3)=[CH:24][CH:23]=[N:22]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.O.C(=O)([O-])O.[Na+].[Cl-].[Na+].O.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.Cl[Pd]Cl>[CH:12]1([CH2:11][N:4]2[CH:5]=[C:6]([O:9][CH3:10])[C:7](=[O:8])[C:2]([C:25]3[N:21]([C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=4)[N:22]=[CH:23][CH:24]=3)=[N:3]2)[CH2:14][CH2:13]1

Komponenten

9

Edukt 3

HCID 11430Potassium CarbonateHCID 580723671-Phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 895861593-chloro-1-(cyclopropylmethyl)-5-methoxypyridazin-4(1H)-one

Produkt 1

HCID 680148501-(cyclopropylmethyl)-5-methoxy-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-oneAusbeute 59,6 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 11714597Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II)KatalysatorHCID 962WaterLösungsmittel2×HCID 1140TolueneLösungsmittelHCID 516892Sodium BicarbonateLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

3-Chloro-1-(cyclopropylmethyl)-5-methoxypyridazin-4(1H)-one (0.133 g), 1-phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.200 g), potassium carbonate (0.171 g) and bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (0.0219 g) were suspended in toluene (3.09 mL) and water (0.309 mL), and the suspension was heated under reflux for 20 hr under an argon atmosphere. The reaction mixture was cooled to room temperature, diluted with water, saturated aqueous sodium hydrogen carbonate solution and saturated brine, extracted with ethyl acetate, dried over anhydrous sodium sulfate, filtered, concentrated, purified by NH silica gel column chromatography (ethyl acetate/hexane→methanol/ethyl acetate) and recrystallized from ethyl acetate/hexane to give the title compound (0.119 g).

Aufarbeitung

  1. temperatureunder reflux for 20 hr under an argon atmosphere
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by NH silica gel column chromatography (ethyl acetate/hexane→methanol/ethyl acetate)
  7. customrecrystallized from ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-eb3e4e029e5b4b15b88a55422355d6cf
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09150588B2

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