Tributyltin Chloride → 1,5,5-trimethyl-3-tributylstannanyl-4,5,6,7-tetrahydro-1H-indazole

Participants

Reaction Conditions

Reaction Steps

In a round-bottomed flask, 3-iodo-1,5,5-trimethyl-4,5,6,7-tetrahydro-1H-indazole (140 mg, 0.48 mmol) was dissolved in THF (3 ml). The colorless solution was cooled to −16° C. (NaCl/ice bath) and isopropylmagnesium chloride (2.0M in THF, 0.27 ml, 0.54 mmol) was added dropwise. The reaction mixture was stirred at −16° C. for 20 min then tributylchlorostannane (0.15 ml, 0.55 mmol) was slowly added. The reaction mixture was allowed to warm to room temperature over 1.5 h then quenched with saturated NH4Cl, diluted with water and extracted with EtOAc (2×). The combined organic layers were washed with water and brine then dried over sodium sulfate, filtered and concentrated to afford 1,5,5-trimethyl-3-tributylstannanyl-4,5,6,7-tetrahydro-1H-indazole as a colorless oil which was used without further purification.

Provenance & Evidence