Tributyltin Chloride → N-methyl-2-tributylstannanyl-isonicotinamide

Participants

Reaction Steps

In a round-bottomed flask, 2-iodo-N-methylisonicotinamide (0.18 g, 0.69 mmol) was dissolved in THF (3.9 mL) and sodium hydride (60% dispersion in mineral oil, 33 mg, 0.83 mmol) was added. The reaction mixture was stirred at room temperature for 10 min then cooled to −16° C. (NaCl/ice bath) and isopropylmagnesium chloride (2.0M solution in THF, 0.39 mL, 0.780 mmol) was added dropwise. The reaction mixture was stirred at −16° C. for 40 min then tributylchlorostannane (0.22 mL, 0.81 mmol) was slowly added. The reaction mixture was allowed to warm to room temperature and stirred for 2 h then 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. The residue was chromatographed over 12 g silica gel with EtOAc/Hexanes (contains 1% Triethylamine) (gradient: 0-30% EtOAc). All fractions containing product were combined and concentrated to afford 89 mg (31%) of N-methyl-2-tributylstannanyl-isonicotinamide as a colorless oil.

Provenance & Evidence