Tributyltin Chloride → 6-tert-butyl-1-methyl-3-tributylstannanyl-1H-indazole
Reaktionsgleichung
[C:1]([C:5]1[CH:13]=[C:12]2[C:8]([C:9](I)=[N:10][N:11]2[CH3:14])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C([Mg]Cl)(C)C.[CH2:21]([Sn:25]([CH2:31][CH2:32][CH2:33][CH3:34])([CH2:27][CH2:28][CH2:29][CH3:30])Cl)[CH2:22][CH2:23][CH3:24]>C1COCC1>[C:1]([C:5]1[CH:13]=[C:12]2[C:8]([C:9]([Sn:25]([CH2:27][CH2:28][CH2:29][CH3:30])([CH2:31][CH2:32][CH2:33][CH3:34])[CH2:21][CH2:22][CH2:23][CH3:24])=[N:10][N:11]2[CH3:14])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
To a solution of 6-tert-butyl-3-iodo-1-methyl-1H-indazole (150 mg, 0.45 mmol) in THF (3 mL) at 0° C. was slowly added isopropylmagnesium chloride (2.0 M in THF, 0.27 mL, 0.54 mmol). The bright yellow heterogeneous reaction mixture was stirred at 0° C. for 1 h then tributylchlorostannane (0.15 mL, 0.54 mmol) was added dropwise. Stirring was continued at 0° C. for 20 min then at room temperature for 3 h. The reaction mixture was quenched with water and extracted with EtOAc (2×). The combined organics were washed with brine then dried over MgSO4 and concentrated to afford 6-tert-butyl-1-methyl-3-tributylstannanyl-1H-indazole as a viscous yellow oil which was used in the next step without further purification.
Aufarbeitung
- customat 0° C.
- stirringStirring
- waitwas continued at 0° C. for 20 min
- waitat room temperature for 3 h
- customThe reaction mixture was quenched with water
- extractionextracted with EtOAc (2×)
- washThe combined organics were washed with brine
- dry with materialthen dried over MgSO4
- concentrationconcentrated
Quellen und Nachweise
- ORD-Eintrag
- ord-1c673ba749194d31b97dcc6cd2cd285d
- Quelldatensatz
- uspto-grants-2014_02
- Patentnummer
- US08658646B2
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