Acetate → HCID 178491350, compound

Participants

Reaction Steps

The preparation was carried out analogously to Example 67, using 0.200 g (0.548 mmol) N-(6-bromopyridin-2-yl)-N′-(2,6-dimethoxybenzyl)guanidine and 2.74 mL (1.369 mmol) of the benzyl zinc bromide solution (0.5 M in tetrahydrofuran) under Pd catalysis with 20 mg (0.055 mmol) [1,1′-bis-(diphenylphosphino)ferrocene]palladium(II) chloride-methylene chloride. The mixture was likewise heated under reflux under a nitrogen atmosphere, first for 4 hr, and then after repeated additions of 2.43 mL (1.213 mmol) of the 0.5 M benzyl zinc bromide solution and 20 mg (0.055 mmol) Pd catalyst for an additional 8 hr, i.e., for a total of 12 hr of heating. After appropriate workup and purification via preparative HPLC (Merck Chromolith RP-18 100×25 mm, eluent: water/acetonitrile/0.1 M acetic acid), 95 mg (0.216 mmol, 40%) pure N-(6-benzylpyridin-2-yl)-N′-(2,6-dimethoxybenzyl)guanidine was obtained in the form of the acetate salt (base/acetate in a ratio of 1:1).

Provenance & Evidence