Sodium hydride → Tert-butyl propyl[5-(tributylstannanyl)-1,3-thiazol-2-yl]carbamate

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(N-BOC)-5-(tributylstannyl)thiazole (200 mg, 0.409 mmole) in DMF (2 mL) was added NaH (60% dispersion in mineral oil, 20 mg, 0.500 mmole) at RT. After gas evolution had ceased 1-iodopropane (0.048 mL, 0.490 mmole) was added and the mixture was heated to 60° C. After stirring overnight the mixture was cooled to RT, diluted with H2O, and extracted with EtOAc (3×). The combined organic layers were washed with H2O and brine, dried (MgSO4), filtered, and concentrated. Flash column chromatography (Biotage-SNAP-25 g SiO2, 0-10% EtOAc/hexanes) gave the title compound (155 mg, 71%) as a clear oil. 1H NMR (400 MHz, CDCl3): δ 7.33 (s, 1 H); 4.11-4.03 (m, 2 H); 1.79-1.69 (m, 1 H); 1.62-1.52 (m, 18 H); 1.38-1.28 (m, 7 H); 1.13-1.05 (m, 7 H); 0.95 (m, 3 H); 0.93-0.84 (m, 9 H).

Provenance & Evidence