2-Bromopyridine → HCID 89572771, compound

Participants

Reaction Steps

To a solution of 2-bromopyridine (449 mg, 2.84 mmol) in THF (10 mL) was added dropwise n-butyl lithium (1.6 N, 1.77 mL, 2.84 mmol) at −78° C. After stirring at the same temperature for 30 minutes, a solution of Example 275B (400 mg, 1.89 mmol) in THF (2 mL) was added. The mixture was stirred at −78° C. for additional 30 minutes and then quenched with aqueous H2SO4 solution (1 N, 5 mL) slowly. The reaction mixture was warmed up to room temperature and partitioned. The aqueous phase was separated and extracted with EtOAc (3×10 mL). The combined organic phases were washed with water (30 mL) and brine (30 mL), dried over Na2SO4, filtered, and concentrated to give the title compound (430 mg, 0.50 mmol, 26.4% yield) as a yellow solid. MS: MS (M+H)+.

Provenance & Evidence