1,2-Dimethoxyethane → 2-(5-{6-[4-(2-{1-[2-Methoxycarbonylamino-2-(tetrahydro-pyran-4-yl)-acetyl]-pyrrolidin-2-yl}-3H-imidazol-4-yl)-phenyl]-naphthalen-2-yl}-1H-imidazol-2-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-[5-(6-Bromo-naphthalen-2-yl)-1H-imidazol-2-yl]-pyrrolidine-1-carboxylic acid tert-butyl ester (2.26 g, 5.11 mmol) and 2-{5-[4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-1H-imidazol-2-yl}-pyrrolidine-1-carboxylic acid benzyl ester (3.00 g, 6.34 mmol) in DME (25 mL) was added Tetrakis(triphenylphosphine)Palladium (0.30 g, 0.26 mmol) and aqueous potassium phosphate (2M, 7.6 mL, 15.2 mmol). The solution was degassed with argon for 15 min and heated to 80° C. for 18 h with stirring. The solution was cooled, filtered and diluted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated. The crude oil was purified by column chromatography (SiO2, 30→100% EtOAc (10% MeOH) in Hexanes) to provide 2-(5-{6-[4-(2-{1-[2-Methoxycarbonylamino-2-(tetrahydro-pyran-4-yl)-acetyl]-pyrrolidin-2-yl}-3H-imidazol-4-yl)-phenyl]-naphthalen-2-yl}-1H-imidazol-2-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester (4.31 g, 84%). LCMS-ESI+: calc'd for C43H44N6O4: 708.34 (M+); Found: 709.58 (M+H+).

Provenance & Evidence