2,5-Dibromopyridine → HCID 86713197, compound

Participants

Reaction Steps

A solution of 2,5-dibromopyridine (5 g, 21 mmol), in dry toluene (200 mL, 0.1 M) is cooled to −75° C. under a blanket of nitrogen. 2.5 M n-BuLi in hexanes (16 mL, 25 mmol, 1.2 eq) is added drop-wise maintaining a temp less than −73° C. and the reaction mixture is stirred at −73° C. to −78° C. for 2 hours. The mixture is then added to a solution of tert-butyl (3-oxopropyl)carbamate (3.66 g, 21 mmol) in toluene (50 mL) at −78° C. The reaction mixture is stirred at −78° C. for 1 hour, before being allowed to warm slowly to room temperature and stirred overnight. The reaction mixture is quenched with saturated ammonium chloride solution (100 ml) and the toluene phase is separated and concentrated. The crude material is purified by chromatography (0-45% ethyl acetate in heptane) to give the title compound (3.1 g). MS (ESI+) m/z 331.0 [M+H].

Provenance & Evidence