Sodium Carbonate → HCID 178489501, compound

Participants

Reaction Conditions

Reaction Steps

0.102 g (0.251 mmol) N-(5-iodopyridin-2-yl)-N′-(2-methoxybenzyl)guanidine, 0.041 g (0.337 mmol) phenylboric acid, 0.075 g (0.708 mmol) sodium carbonate, and 0.015 g (0.013 mmol) tetrakis-(triphenylphosphine) palladium(0) were combined and added to 7.0 mL of a solvent mixture of 1,2-dimethoxyethane/water/ethanol (7:3:2). The mixture was degassed under a strong nitrogen stream and heated for 110 min at 120° C. in a CEM microwave (150 watts) and reacted. After filtration through a Millipore filter (Ø=25 mm, 0.45 μm) the solvent was removed under vacuum and the crude mixture was purified via preparative HPLC (Merck Chromolith RP-18 100×25 mm, eluent: water/acetonitrile/0.1 M acetic acid), with a flow rate of 20 mL/min and with gradients of 10% to 30% of the acetonitrile fraction in 10 min. Following freeze drying with a lyophilizing agent, 23 mg of the desired product N-(2-methoxybenzyl)-N′-(5-phenylpyridin-2-yl)guanidine was isolated.

Provenance & Evidence