Tributyltin Chloride → HCID 178448228, compound

Participants

Reaction Steps

In a round-bottomed flask, 7-(tert-butyl-dimethyl-silanyloxymethyl)-3-iodo-1H-indazole (200 mg, 0.52 mmol) was dissolved in THF (2.8 ml) and sodium hydride (60% in mineral oil, 25 mg, 0.63 mmol) was added. The reaction mixture was stirred at room temperature for 10 min then cooled to −16° C. (NaCl/ice bath) and isopropylmagnesium chloride (2.0 M in THF, 0.36 ml, 0.72 mmol) was added dropwise. The reaction mixture was stirred at −16° C. for 30 min then tributylchlorostannane (0.16 ml, 0.59 mmol) was slowly added. The reaction mixture was allowed to warm to room temperature and stirred for 2.5 h then quenched with saturated aqueous NH4Cl and extracted with EtOAc (2×). The organic layers were washed with water and brine then dried over sodium sulfate, filtered and concentrated to give 7-(tert-butyl-dimethyl-silanyloxymethyl)-3-tributylstannanyl-1H-indazole as a yellow oil which was used without further purification.

Provenance & Evidence