Sodium Carbonate → HCID 68807013, compound

Participants

Reaction Steps

2-(4-Bromo-2-chloro-phenylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (1 g, 2.5 mmol), 2-(methylthio)benzene boronic acid (0.5 g, 3 mmol), and tetrabutylammonium bromide (40 mg, 0.12 mmol) were combined in 10 mL toluene, added 2 mL of a 2M aqueous Na2CO3 solution followed by tetrakistriphenylphosphine palladium(0) (0.14 g, 0.12 mmol). Heated reaction at reflux for 5 hours, cooled, dissolved in EtOAc (150 mL), washed with water (3×50 mL), brine (50 mL), dried with MgSO4, filtered, and concentrated. Purified on a silica gel column eluted using an automated system with gradient of 0-50% EtOAc in hexanes over 40 minutes. Combined and concentrated pure fractions to yield title compound as a white foam. (1.01 g, 91%) APCI (AP−): 445.1, 447.1 (M−H)−.

Provenance & Evidence