Tributyltin Chloride → 4-Pyrrol-1-yl-2-tributylstannanyl-pyridine

Participants

Reaction Conditions

Reaction Steps

In a round-bottomed flask, 2-bromo-4-(1H-pyrrol-1-yl)pyridine (0.20 g, 0.90 mmol) was dissolved in THF (6 mL). The light yellow solution was cooled to 0° C. and isopropylmagnesium chloride lithium chloride complex (1.3 M solution in THF, 0.78 mL, 1.0 mmol) was added dropwise. The reaction mixture was stirred at 0° C. for 40 min and at room temperature for 2 h. The reaction mixture was cooled to 0° C. and tributyltin chloride (0.28 mL, 1.03 mmol) was slowly added. After the addition was complete, the ice bath was removed and the reaction mixture was stirred at room temperature for 1.5 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 ˜5 mL brine then dried over sodium sulfate, filtered and concentrated to provide 4-pyrrol-1-yl-2-tributylstannanyl-pyridine as a light brown oil which was used without further purification.

Provenance & Evidence