Sodium Carbonate → HCID 59627653, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 4-(6-carbamoyl-3,5-dimethylpyrazin-2-yl)phenylboronic acid (175 mg, 0.65 mmol) and methyl 2-(3,5-difluoro-4-(trifluoromethylsulfonyloxy)phenyl)propanoate (Intermediate 21-2; 200 mg, 0.57 mmol) and Sodium carbonate (0.467 mL, 0.93 mmol), tetrakis(triphenylphosphine)palladium(0) (41.1 mg, 0.04 mmol) and lithium chloride (42.6 mg, 1.01 mmol) in DME (14.300 mL) was degassed and then stirred at 85° C. for 17 hours. The reaction mixture was partitioned between EtOAc (10 mL) and saturated brine (15 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 50% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford methyl 2-(4′-(6-carbamoyl-3,5-dimethylpyrazin-2-yl)-2,6-difluorobiphenyl-4-yl)propanoate (164 mg, 67.1%) as a white solid.

Provenance & Evidence