Tri-o-tolylphosphine → N-((5-ethoxy-2-fluoro-3-isopropoxyphenyl)(4-(3-(methylsulfonyl)phenyl)-1-trityl-1H-imidazol-2-yl)methyl)-4-(5-methyl-1,2,4-oxadiazol-3-yl)benzenamine

Participants

Reaction Conditions

Reaction Steps

To a degassed mixture of Intermediate 66.3 (48 mg, 0.063 mmol), 3-(methylsulfonyl)phenylboronic acid (16 mg, 0.0755 mmol), tri-ortho-tolylphosphine (3.8 mg, 0.0.13 mmol) and NaHCO3 (21.7 mg, 0.258 mmol) in 2 mL DME/H2O (3:1), was added Pd(OAc)2 (1.4 mg, 0.0063 mmol). The mixture was stirred at 80° C. for 1.5 h, then was diluted with EtOAc, washed with H2O and brine, dried (Na2SO4), and concentrated. The crude mixture was purified by flash chromatography (0 to 100% EtOAc/hexanes gradient) to afford 8 mg of Intermediate 66.4 as a colorless solid.

Provenance & Evidence