Potassium Carbonate → 4-{2-[(2S,4S)-1-((S)-2-Methoxycarbonylamino-3-methyl-butyryl)-4-methyl-pyrrolidin-2-yl]-3H-naphth[1,2-d]imidazol-7-yl}-3-trifluoromethoxy-benzoic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

A solution of ((S)-2-methyl-1-{(2S,4S)-4-methyl-2-[7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3H-naphtho[1,2-d]imidazol-2-yl]-pyrrolidine-1-carbonyl}-propyl)-carbamic acid methyl ester (250 mg, 0.48 mmol; Preparation 13), 4-bromo-3-trifluoromethoxy-benzoic acid methyl ester (140 mg, 0.47 mmol), and potassium carbonate (323 mg, 2.34 mmol) in toluene (2 mL) and water (0.5 mL) was purged with nitrogen for 5 min, then Pd(dppf)Cl2 (20.5 mg, 0.029 mmol) was added. The reaction mixture was stirred at 100° C. overnight, diluted with ethyl acetate (50 mL), washed with water (2×5 mL). The organic layer was dried over magnesium sulfate, filtered, concentrated, and purified by silica gel chromatography (EtOAc/hexane 20 to 100%) to give the title intermediate (284 mg, 97% yield). (m/z): [M+H]+ calcd for C32H32F3N4O6 627.24 found 627.3.

Provenance & Evidence