Reaktionsgleichung
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][N:2]=1.[Br:7][C:8]1[CH:13]=[CH:12][C:11]([C@H:14]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[CH3:28])[CH2:15][C:16](N(OC)C)=[O:17])=[CH:10][CH:9]=1.CC(N=P(N=P(N(C)C)(N(C)C)N(C)C)(N=P(N(C)C)(N(C)C)N(C)C)N=P(N(C)C)(N(C)C)N(C)C)(C)C>C1COCC1.[I-].[Zn+2].[I-]>[Br:7][C:8]1[CH:9]=[CH:10][C:11]([C@H:14]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[CH3:28])[CH2:15][C:16]([C:5]2[CH:4]=[CH:3][N:2]=[N:1][CH:6]=2)=[O:17])=[CH:12][CH:13]=1Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
To a solution of pyridazine (250 mg, 3.12 mmol) and (R)-3-(4-bromophenyl)-N-methoxy-N-methyl-3-o-tolylpropanamide (1.81 g, 4.99 mmol) in THF (10 mL) was added zinc iodide (996 mg, 3.12 mmol). The suspension was stirred for 10 min. at ambient temperature. The reaction mixture was cooled to −78° C., then N′″-(1,1-dimethylethyl)-N,N′,N″-tris[tris(dimethyl-amino)phosphoranylidene]-phosphorimidic triamide solution (“Schwesinger P4 base”; 1 M in hexane 4.68 mL, 4.68 mmol) was added. The reaction mixture was allowed to reach room temperature over 16 h, then partitioned between sat, aq. ammonium chloride solution and dichloromethane. The organic layer was dried over magnesium sulfate, filtered, and evaporated. Chromatography (SiO2; heptane-ethyl acetate gradient) produced the title compound 30 mg, 3%), while the most of the starting material was recovered (1.51 g, 83%). Light yellow gum, MS: 381.1 [M+H]+.
Aufarbeitung
- temperatureThe reaction mixture was cooled to −78° C.
- waitto reach room temperature over 16 h
- custompartitioned
- dry with materialThe organic layer was dried over magnesium sulfate
- filtrationfiltered
- customevaporated
Quellen und Nachweise
- ORD-Eintrag
- ord-70e44b26244040a998e197a5250a6a87
- Quelldatensatz
- uspto-grants-2015_07
- Patentnummer
- US09090565B2
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