Tributyltin Chloride → HCID 57516639, compound

Participants

Reaction Conditions

Reaction Steps

In a round-bottomed flask, 2-bromo-4-(1H-pyrazol-1-yl)pyridine (0.15 g, 0.67 mmol) was dissolved in THF (4.4 mL). The light yellow solution was cooled to 0° C. and isopropylmagnesium chloride lithium chloride complex (1.3 M solution in THF, 0.57 mL, 0.74 mmol) was added dropwise. The reaction mixture was stirred at 0° C. for 25 min and at room temperature for 1.5 h. Additional isopropylmagnesium chloride lithium chloride complex (1.3 M solution in THF, 0.29 mL, 0.38 mmol) was added and the reaction mixture was stirred at room temperature for 30 min. The reaction mixture was cooled to 0° C. and tributyltin chloride (0.21 mL, 0.77 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 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-pyrazol-1-yl-2-tributylstannanyl-pyridine as a light brown oil which was used without further purification.

Provenance & Evidence