Acetate → HCID 178489510, compound

Participants

Reaction Conditions

Reaction Steps

The preparation was carried out analogously to Example 56, using 0.200 g (0.506 mmol) N-(3-bromopyridin-2-yl)-N′-(2-methoxybenzyl)guanidine acetate, 0.106 g (0.759 mmol) (4-fluorophenyl)boric acid, 0.160 g (1.518 mmol) sodium carbonate, and 0.038 g (0.033 mmol) tetrakis-(triphenylphosphine)palladium(0). The mixture was likewise heated in a reaction block for 19 hr at 110° C. under a nitrogen atmosphere. Despite prolonging the reaction time to a total of 6 days and renewed addition of the starting materials sodium carbonate, (4-fluorophenyl)boric acid, and catalyst, the reaction reached an end point at which the starting material/product-ratio of 1:1 had not changed. After termination of the reaction, appropriate workup, and purification via preparative HPLC, 20 mg (0.048 mmol, 9.4%) pure N-[3-(4-fluorophenyl)pyridin-2-yl]-N′-(2-methoxybenzyl)guanidine was obtained in the form of the acetate salt (base/acetate in a ratio of 1:1).

Provenance & Evidence