Sodium Carbonate → 2-(2-Fluoro-5-methylphenyl)pyridin-4-amine

Participants

Reaction Steps

Bis(triphenylphosphine)palladium chloride (0.406 g, 0.578 mmol), tert-butyl 2-bromopyridin-4-ylcarbamate (250 mg, 0.915 mmol), and 2-fluoro-5-methylphenylboronic acid (1.157 g, 7.51 mmol) and sodium carbonate (0.458 ml, 0.915 mmol) were combined in dioxane (10 mL) and heated to reflux for 5 hours. The reaction mixture was cooled, evaporated to remove most of the solvent, and partitioned between brine and EtOAc. The organic layer was separated and dried over Na2SO4, filtered, and concentrate under vacuum to give a residue which was purified by NH silica column chromatography eluting with Hex/EtOAc 1:1 to give a residue which was further purified by repeating the silica column chromatography using the same conditions to give the title compound (986 mg) as clear oil which solidified on standing. ESI-MS: m/z 203.1 (M+H).

Provenance & Evidence