Sodium Carbonate → HCID 178476654, compound

Participants

Reaction Conditions

Reaction Steps

0.251 g (0.609 mmol) N-(2,6-dimethoxybenzyl)-N′-(5-iodopyridin-2-yl)guanidine, 0.100 g (0.792 mmol) phenylboric acid, 0.194 g (1.829 mmol) sodium carbonate, and 0.035 g (0.030 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 reacted by heating for 60 min at 120° C. in a CEM microwave (230 watts). To prevent precipitation of product, the reaction mixture was first diluted with dichloromethane and then shaken out with water. After separation of the phases the aqueous phase was repeatedly extracted with dichloromethane, and the combined organic phases were neutralized with 150 mL 2 N sodium hydroxide solution and then washed again with water (2×100 mL). After drying over magnesium sulfate and evaporation of the solvent, purification was performed 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 40% of the acetonitrile fraction in 15 min. Following freeze drying with a lyophilizing agent, 16 mg of the desired product N-(2,6-dimethoxybenzyl)-N′-(5-phenylpyridin-2-yl)guanidine was isolated in the form of the acetate salt (base/acetate in a ratio of 1:1).

Provenance & Evidence