Sodium Carbonate → HCID 178491364, compound

Participants

Reaction Conditions

Reaction Steps

The preparation was carried out analogously to Example 56, using 0.200 g (0.470 mmol) N-(3-bromopyridin-2-yl)-N′-(2,6-dimethoxybenzyl)guanidine acetate, 0.086 g (0.705 mmol) phenylboric acid, 0.149 g (1.411 mmol) sodium carbonate, and 0.038 g (0.033 mmol) tetrakis-(triphenylphosphine)palladium(0). The mixture was likewise heated in a reaction block for 20 hr at 110° C. under a nitrogen atmosphere. However, after this reaction time the starting material/product ratio was still 1:1. Therefore, further heating was performed for 16 hr, and then for an additional 25 hr. After a total reaction time of 61 hr the reaction was terminated due to increasing formation of by-products. After appropriate workup and purification via preparative HPLC, 41 mg pure N-(2,6-dimethoxybenzyl)-N′-(3-phenylpyridin-2-yl)guanidine was obtained in the form of the acetate salt (base/acetate in a ratio of 1:1.2).

Provenance & Evidence