Tributyltin Chloride → 7-Chloro-2-(tributylstannyl)thieno[3,2-b]pyridine

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Reaction Steps

In a round bottom flask, 7-chloro-2-iodothieno[3,2-b]pyridine (200 mg, 0.68 mmol) was suspended in THF (6 mL). The reaction mixture was cooled with a NaCl-ice bath (−12 to −8° C. internal temp) and isopropylmagnesium chloride (2.0 M in THF, 0.406 mL, 0.812 mmol) was added dropwise. The reaction mixture was stirred for 1 h at the same temperature, and then tributyltin chloride (0.29 mL, 1.08 mmol) was slowly added. The reaction mixture was allowed to warm to room temperature over ˜1 h then quenched with an aqueous solution of NH4Cl (20 mL) and extracted with EtOAc (30 mL). The organic layer was dried over Na2SO4 and evaporated to dryness. The crude residue was purified by column chromatography (SiO2-11 g-Et3N 2%, hexanes 100% 5 min, to hexanes:EtOAc, 9:1 in 15 min) to isolate 162 mg (52%) of 7-chloro-2-tributylstannanyl-thieno[3,2-b]pyridine as a colorless oil.

Provenance & Evidence