Tributyltin Chloride → HCID 57516633, compound

Participants

Reaction Conditions

Reaction Steps

In a round-bottomed flask, 2-iodo-4-thiophen-2-yl-pyridine (150 mg, 0.52 mmol) was dissolved in THF (3.2 mL). The light yellow solution was cooled to −16° C. (NaCl/ice bath) and isopropylmagnesium chloride (2.0M solution in THF, 0.30 mL, 0.60 mmol) was added dropwise. The reaction mixture was stirred at −16° C. for 20 min then tributylchlorostannane (0.17 mL, 0.63 mmol) was slowly added. After the addition, the reaction mixture was allowed to warm to room temperature and stirred for 1 h. The reaction mixture was quenched with saturated NH4Cl solution and then extracted with 50 mL EtOAc (2×). The combined organic layers were washed with 5 mL water and once with 5 mL brine then dried over sodium sulfate, filtered and concentrated to afford 4-thiophen-2-yl-2-(tributylstannanyl)pyridine a light brown oil which was used without further purification.

Provenance & Evidence