Tributyltin Chloride → 6-Fluoro-3-methylsulfanyl-1-tributylstannanyl-imidazo[1,5-a]pyridine

Participants

Reaction Conditions

Reaction Steps

In a round-bottomed flask, 6-fluoro-1-iodo-3-methylsulfanyl-imidazo[1,5-a]pyridine (109 mg, 0.35 mmol) was dissolved in THF (3 ml). The light brown solution was cooled to −16° C. (NaCl/ice bath) and isopropylmagnesium chloride (2.0 M in THF, 0.21 ml, 0.42 mmol) was added dropwise. The reaction mixture was stirred at −16° C. for 20 min then tributylchlorostannane (0.11 ml, 0.40 mmol) was slowly added. The reaction mixture was allowed to warm to room temperature and stirred for 2 h then quenched with saturated aqueous NH4Cl and extracted with ethyl acetate (2×). The combined organic layers were washed with water and brine then dried over sodium sulfate, filtered and concentrated to give 6-fluoro-3-methylsulfanyl-1-tributylstannanyl-imidazo[1,5-a]pyridine as a brown oil which was used without further purification.

Provenance & Evidence