Tributyltin Chloride → 6-chloro-3-(tributylstannyl)-1H-indazole
Reaktionsgleichung
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](I)=[N:7][NH:8]2)=[CH:4][CH:3]=1.[H-].[Na+].C([Mg]Cl)(C)C.[CH2:19]([Sn:23](Cl)([CH2:28][CH2:29][CH2:30][CH3:31])[CH2:24][CH2:25][CH2:26][CH3:27])[CH2:20][CH2:21][CH3:22]>C1COCC1.O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([Sn:23]([CH2:24][CH2:25][CH2:26][CH3:27])([CH2:28][CH2:29][CH2:30][CH3:31])[CH2:19][CH2:20][CH2:21][CH3:22])=[N:7][NH:8]2)=[CH:4][CH:3]=1Komponenten
8
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 3
Reaktionsbedingungen
- Temperatur
- -16 °C
Versuchsvorschrift
To a stirred solution of 6-chloro-3-iodo-1H-indazole (1.11 g, 4.0 mmol) in THF (25 mL) was added sodium hydride (192 mg, 4.8 mmol). After 15 min the mixture was cooled to −16° C. Isopropylmagnesium chloride (3.00 mL, 6.00 mmol) was added dropwise and the mixture stirred at −16° C. for 2 h. Tributyltin chloride (1.56 g, 1.3 mL, 4.8 mmol) was then added and the reaction mixture warmed to room temperature. After 15 h the mixture was diluted with water and ethyl acetate. The organic layer was washed with brine, dried (sodium sulfate) filtered and concentrated in vacuo. The crude brown oil was used directly in the next step without further purification.
Aufarbeitung
- temperaturethe reaction mixture warmed to room temperature
- washThe organic layer was washed with brine
- dry with materialdried (sodium sulfate)
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe crude brown oil was used directly in the next step without further purification
Quellen und Nachweise
- ORD-Eintrag
- ord-1828d87cc56c406c8806356a62a323a7
- Quelldatensatz
- uspto-grants-2014_02
- Patentnummer
- US08658646B2
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