N-bromobutanimide → tert-Butyl (S)-(1-(5-amino-3,6-dibromopyridin-2-yl)-2-(3,5-difluorophenyl)ethyl)carbamate

Participants

Reaction Steps

A solution of (S)-tert-butyl (1-(5-amino-3-bromopyridin-2-yl)-2-(3,5-difluorophenyl)ethyl)carbamate (46A, 960 mg, 2.24 mmol) in 20 mL of acetonitrile was cooled to 0° C. and treated with N-bromosuccinimide (399 mg, 2.24 mmol) as a solution in 20 mL of acetonitrile. After 5 min, the reaction mixture was partitioned with EtOAc and saturated aqueous NaHCO3. The organic layer was separated and washed with brine, then dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with EtOAc/hexanes to afford the title product. MS (m/z): 507.52 [M+H]+.

Provenance & Evidence