Sodium Carbonate → HCID 68721785, compound

Participants

Reaction Conditions

Reaction Steps

N-(6-Chloro-5-methylpyridin-2-yl)-1-(4-methoxyphenyl)cyclopropane carboxamide (63 mg, 0.20 mmol) was dissolved in 1,2-dimethoxyethane (2.0 mL) in a reaction tube. 2-Methoxypyridin-4-ylboronic acid (46 mg, 0.30 mmol), aqueous 2 M sodium carbonate (0.20 mL), and (Ph3P)4Pd (12 mg, 0.010 mmol) were added and the reaction mixture was heated at 80° C. under N2 atmosphere for 18 hours. Since the reaction was incomplete, it was re-treated with same amount of boronic acid, base and Pd catalyst and heated at 80° C. for 18 hours. The resulting material was cooled to room temperature, filtered, and evaporated under reduced pressure. The crude product was dissolved in DMSO (2 mL), filtered, and purified by reverse phase preparative HPLC to yield N-(2′-methoxy-3-methyl-2,4′-bipyridin-6-yl)-1-(4-methoxyphenyl)cyclopropane carboxamide. ESI-MS m/z calc. 389.2. found 390.5 (M+1)+. Retention time 1.84 minutes.

Provenance & Evidence