Acetate → HCID 178489505, compound

Participants

Reaction Steps

The preparation was carried out analogously to Example 67, using 0.200 g (0.597 mmol) N-(6-bromopyridin-2-yl)-N′-(2-methoxybenzyl)guanidine and 2.98 mL (1.491 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 9 hr, and then after repeated additions of 2.98 mL (1.491 mmol) of the 0.5 M benzyl zinc bromide solution and 20 mg (0.055 mmol) Pd catalyst the mixture was heated for an additional 8 hr and stirred for an additional 8 hr. After appropriate workup and purification via two preparative HPLC procedures (1× via Waters, XTerra RP-18 and Merck, 1× Chromolith RP-18 100×25 mm, each eluent: water/acetonitrile/0.1 M acetic acid), 18 mg (0.044 mmol, 7%) N-(6-benzylpyridin-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