Tributyltin Chloride → tert-butyl N-(5-(tributylstannyl)-1,3-thiazol-2-yl)carbamate

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A solution of tert-butyl thiazol-2-ylcarbamate (15.0 g, 75 mmol), in THF (200 mL) was stirred at −78° C. and then n-butyl lithium (63 mL, 157 mmol) was added dropwise over 15 minutes. The resulting solution was stirred at −78° C. for 30 minutes, and then tributyltin chloride (22 mL, 82 mmol) was then added dropwise. The resulting pale yellow mixture was stirred for 30 minutes at −78° C. The bath was then removed, and the mixture was allowed to warm to room temperature. The reaction was then stirred for 2.5 hours. The reaction mixture was quenched with a saturated NH4Cl solution (300 mL). The layers were separated, and the aqueous layer was extracted with ether (3×100 mL). The organic layers were combined, washed with brine (300 mL), dried over MgSO4, filtered, and concentrated. The crude product was adsorbed onto a plug of silica gel and chromatographed through a Redi-Sep pre-packed silica gel column (330 g), eluting with a gradient of 10% to 20% EtOAc in hexanes, to provide the title compound (30 g, 81%) LCMS (M+H+) 490.1 calc. for C20H38N2O2SSn 490.1; 1H NMR (400 MHz, CDCl3) δ ppm 7.31 (s, 1H), 1.59 (s, 9H), 1.30 (tt, 6H), 1.54 (t, 6H), 1.10 (qt, 6H), 0.80 (t, 9H).

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