Tributyltin Chloride → 5-(tert-butyldimethylsilyloxy)-1-methyl-3-(tributylstannyl)-1H-indazole

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

In a round-bottomed flask, 5-(tert-butyl-dimethyl-silanyloxy)-3-iodo-1-methyl-1H-indazole (140 mg, 0.36 mmol) was dissolved in THF (2 ml). The solution was cooled to −16° C. (NaCl/ice bath) and isopropylmagnesium chloride (2.0 M in THF, 0.22 ml, 0.44 mmol) was added dropwise. The reaction mixture was stirred at −16° C. for 20 min then tributylchlorostannane (0.11 ml, 0.41 mmol) was slowly added. The reaction mixture was allowed to warm to room temperature over 1.5 h then quenched with saturated aqueous NH4Cl and extracted with EtOAc (2×). The combined organic layers were washed with water and brine then dried over sodium sulfate, filtered and concentrated to provide 5-(tert-butyl-dimethyl-silanyloxy)-1-methyl-3-tributylstannanyl-1H-indazole as a light yellow oil which was used without further purification.

Herkunft & Nachweise