Sodium Carbonate → 1-(4'-Fluoro-biphenyl-4-ylmethyl)-3-[3-(4-fluoro-phenoxy)-propyl]-1,3-dihydro-benzoimidazol-2-ylideneamine

Participants

Reaction Conditions

Reaction Steps

Nitrogen was bubbled through a mixture of 1-(4-bromo-benzyl)-3-[3-(4-fluoro-phenoxy)-propyl]-1,3-dihydro-benzoimidazol-2-ylideneamine (80 mg, 0.18 mmol) and 4-fluorophenyl boronic acid (37 mg, 0.26 mmol) in 3:1 MeOH/1,4-dioxane (3 ml) at rt for 10 min before a solution of 2M Na2CO3 (0.17 ml, 0.35 mmol) was introduced. The suspension was degassed for a further 2 min and then PdCl2(dppf) (14 mg, 0.02 mmol) was added. The reaction mixture was sealed and heated to 100° C. where it was maintained for 16 h. After this time, the suspension was cooled to rt and filtered through Celite®. The filtrate was concentrated under reduced pressure and the crude product that remained was purified by preparative HPLC to provide 1-(4′-fluoro-biphenyl-4-ylmethyl)-3-[3-(4-fluoro-phenoxy)-propyl]-1,3-dihydro-benzoimidazol-2-ylideneamine (30 mg, 36%). HPLC-MS 470 [M+1]+.

Provenance & Evidence