Diisopropylethylamine → 5-bromo-2-((1S)-2-hydroxy-1-{3-[(trimethylsilyl)ethynyl]benzyl}ethyl)isoindolin-1-one

Participants

Reaction Steps

A solution of methyl 4-bromo-2-(bromomethyl)benzoate (0.75 g, 2.4 mmol), (2S)-2-amino-3-{3-[(trimethylsilyl)ethynyl]phenyl}propan-1-ol (0.60 g, 2.4 mmol) and N,N-diisopropylethylamine (2.1 mL, 12 mmol) in 1-butanol (2 mL) in a sealed tube was stirred at 140° C. for 2 h. The solvent was removed under vacuum and the residue was eluted with 0-100% EtOAc in hexanes giving 0.78 g (73% yield) of the pure desired product as off white solid. LC/MS found: 442.0 (M+H)+.

Provenance & Evidence