Potassium Phosphate, Tribasic → HCID 69671794, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-{5-[4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-1H-imidazol-2-yl}-2-aza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester (0.19 g, 0.41 mmol) in DME (2.0 mL) was added 3-[5-(4-Bromo-phenyl)-1H-imidazol-2-yl]-2-aza-bicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester (0.16 g, 0.41 mmol), Tetrakis(triphenylphosphine)Palladium (0.05 g, 0.04 mmol) and aqueous potassium phosphate (2 M, 0.60 mL, 1.2 mmol). The solution was degassed with argon for 15 min and heated to 80° C. for 18 h with stirring. The solution was cooled diluted with EtOAc and filtered. The filtrate was washed with H2O and brine. The organic layers were dried over Na2SO4 and concentrated. The crude oil was purified by column chromatography (SiO2, 30→100% EtOAc (10% MeOH) in Hexanes to 80% MeOH in EtOAc). The desired fractions were concentrated and combined with the filtered solid to provide 3-(5-{4′-[2-(2-tert-Butoxycarbonyl-2-aza-bicyclo[3.1.0]hex-3-yl)-3H-imidazol-4-yl]-biphenyl-4-yl}-1H-imidazol-2-yl)-2-aza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester (0.17 g, 62%). LCMS-ESI+: calc'd for C39H46N6O4: 662.36 (M+); Found: 663.39 (M+H+).

Provenance & Evidence