Acetate → HCID 178491348, compound

Participants

Reaction Steps

The preparation was carried out analogously to Example 67, using 0.200 g (0.485 mmol) N-(2,6-dimethoxybenzyl)-N′-(5-iodopyridin-2-yl)guanidine and 2.43 mL (1.213 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 a nitrogen atmosphere, first under reflux for 6 hr, and then after repeated additions of 2×2.43 mL (1.213 mmol) of the 0.5 M benzyl zinc bromide solution and the same quantity of Pd catalyst for an additional 6 hr and 4 hr, respectively, for a total of 16 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), 48 mg (0.109 mmol, 23%) pure N-(5-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