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

Participants

Reaction Conditions

Reaction Steps

A suspension 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), 0.086 g (1.0 mmol) of cyclopropyl boronic acid and 0.573 g (2.7 mmol) of tribasic potassium phosphate in 10 ml of toluene was treated with 0.30 ml of water, followed by 0.031 g (0.11 mmol) of tricyclohexylphosphine and 0.012 g (0.055 mmol) of palladium(II)acetate. This reaction mixture was heated up to 100° C., stirred for 18 hours at this temperature and subsequently cooled down to RT. The reaction mixture was then poured into crashed ice and extracted twice with EtOAc; 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 4:1) to give 0.077 g (33%) of the title compound as light yellow oil. MS: 463.4 (MH+).

Provenance & Evidence