4-Bromobenzoyl chloride → (R)-tert-butyl 3-(4-bromo-N-(3-chloropyridin-2-yl)benzamido)piperidine-1-carboxylate

Participants

Reaction Steps

To a solution of Preparation 1 (R)-tert-butyl 3-((3-chloropyridin-2-yl)amino)piperidine-1-carboxylate (100 g, 321 mmol) and 4-bromobenzoyl chloride (73.7 g, 336 mmol) in dry THF (500 mL) was added 1 M lithium bis(trimethylsilyl)amide (362 mL, 362 mmol) dropwise at 0° C. The reaction mixture was warmed and stirred at room temperature overnight. The reaction was quenched with water and extracted with EtOAc (3×1000 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered and the filtrate was concentrated in vacuo. The residue was purified by chromatography on silica gel to give afford the title compound as a yellow solid (100 g, 63%).

Provenance & Evidence