Potassium Phosphate, Tribasic → [5-(4-Fluoro-phenyl)-2-(3-hexyl-phenyl)-3-methyl-3H-imidazol-4-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone

Participants

Reaction Conditions

Reaction Steps

To a solution of 0.275 g (0.50 mmol) of [2-(3-hexyl-phenyl)-5-iodo-3-methyl-3H-imidazol-4-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone (example 2) and 0.140 g (1.0 mmol) of 4-fluorophenyl boronic acid in 10 ml of DMF was added drop by drop 2.50 ml of tribasic potassium phosphate (2 M in water), followed by 0.029 g (0.025 mmol) of tetrakis-(triphenylphosphine)-palladium. This reaction mixture was stirred at 80° C. for two hours and subsequently cooled down to RT, then poured into crashed ice and extracted three times with CH2Cl2; the organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography (CH2Cl2/MeOH 1:0 to 9:1) to give 0.20 g (76%) of the title compound as light yellow oil. MS: 517.4 (MH+).

Provenance & Evidence