Sodium Carbonate → HCID 68805882, compound

Participants

Reaction Steps

(2R,4R)-2-(4-Bromo-2-fluoro-phenylcarbamoyl)-4-(tert-butyl-dimethyl-silanyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester (5.7 g, 10 mmol), 2-(methylthio)benzene boronic acid (2.1 g, 12.6 mmol), and tetrabutylammonium bromide (0.17 g, 0.52 mmol) were combined in 50 mL toluene, added 10 mL of a 2M aqueous Na2CO3 solution followed by tetrakistriphenylphosphine palladium(0) (0.61 g, 0.52 mmol). Heated reaction at reflux for 4 hours, cooled, dissolved in EtOAc (250 mL), washed with water (200 mL), brine, dried with MgSO4, filtered, and concentrated in the presence of 15 g coarse silica. Slurried silica in mobile phase and loaded onto a silica gel column, eluted with 25% EtOAc in hexanes. Combined and concentrated fractions to yield title compound. (4.1 g, 70%) APCI (AP−): 559.3 (M−H)−.

Provenance & Evidence