4-Bromobenzoyl chloride → tert-butyl (3R)-3-[(4-bromobenzoyl)(1-methyl-1H-pyrrolo[2,3-c]pyridin-7-yl)amino]piperidine-1-carboxylate

Participants

Reaction Steps

To a solution of Preparation 4 (R)-tert-butyl 3-((1-methyl-1H-pyrrolo[2,3-c]pyridin-7-yl)amino)piperidine-1-carboxylate (45.0 g, 136 mmol) and 4-bromobenzoyl chloride (31.3 g, 143 mmol) in dry THF (250 mL) was added 1 M lithium bis(trimethylsilyl)amide (163 mL, 163 mmol) dropwise at 0° C. The reaction mixture was warmed to room temperature and stirred for 15 h. The reaction was quenched with aqueous NH4Cl and extracted with EtOAc (3×500 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 recrystallization (petroleum ether:EtOAc=2:1) to afford the title compound as an off-white solid (50 g, 72%).

Provenance & Evidence