Water → 3-(4-Chloro-phenyl)-6-[4-(4-pyrrolidin-1-ylmethyl-phenyl)-but-1-ynyl]-pyridazin

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Reaktionsgleichung

C(N(CC)CC)C.Cl[C:9]1[N:10]=[N:11][C:12]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)=[CH:13][CH:14]=1.[CH2:22]([C:26]1[CH:37]=[CH:36][C:29]([CH2:30][N:31]2[CH2:35][CH2:34][CH2:33][CH2:32]2)=[CH:28][CH:27]=1)[CH2:23][C:24]#[CH:25].O>CN(C=O)C.[Cu]I>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([C:12]2[N:11]=[N:10][C:9]([C:25]#[C:24][CH2:23][CH2:22][C:26]3[CH:37]=[CH:36][C:29]([CH2:30][N:31]4[CH2:35][CH2:34][CH2:33][CH2:32]4)=[CH:28][CH:27]=3)=[CH:14][CH:13]=2)=[CH:16][CH:17]=1

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

Under an argon atmosphere 0.1 mL (0.72 mmol) triethylamine, 3 mg (0.02 mmol) CuI and 8 mg (0.01 mmol) bis-triphenylphosphane-palladium(II)-chloride are added to a solution of 77 mg (0.34 mmol) 3-chloro-6-(4-chloro-phenyl)-pyridazine and 73 mg (0.34 mmol) 1-(4-but-3-ynyl-benzyl)-pyrrolidine (Example 2e) in 4 mL DMF and the reaction mixture is stirred for 20 min at 100° C. and at 300 W in the microwave. The reaction mixture is combined with 10 mL water, extracted with 10 mL EtOAc and the organic phase is washed with water and dried over Na2SO4. After the desiccant and solvent have been eliminated the residue is purified by chromatography (silica gel, EtOAc/MeOH/NH3 90:10:1).

Aufarbeitung

extractionextracted with 10 mL EtOAc
washthe organic phase is washed with water
dry with materialdried over Na2SO4
customis purified by chromatography (silica gel, EtOAc/MeOH/NH3 90:10:1)

Quellen und Nachweise

ORD-Eintrag: ord-05ee01884f09455dbae81d294c7d2f37
Quelldatensatz: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08618132B2

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