Sodium hydride → HCID 57527167, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 6-amino-5-bromonicotinate (0.780 g, 3.18 mmol) and isopropyl isothiocyanate (0.34 mL, 3.19 mmol) in DMF (8 mL) was added sodium hydride (60% oil dispersion) at 0° C. in one portion. The mixture was heated at 65° C. for 20 hr, and then at 75° C. for 40 hr. After it cooled to rt, the reaction was quenched with 1N HCl (5 mL). The mixture was poured into saturated NaHCO3 solution and extracted with AcOEt (3×40 mL). The combined extract was washed with 10% lithium chloride solution (2×30 mL) and dried over anhydrous MgSO4. The title compound (0.291 g, 34% yield) was isolated as a white solid by flash chromatography (60% AcOEt/hexane).

Provenance & Evidence