Cesium carbonate → Methyl 2-(6-methoxy-3-pyridinyl)aminonicotinate

Participants

Reaction Conditions

Reaction Steps

5.0 g (29 mmol) of methyl 2-chloronicotinate and 4.3 g (35 mmol) of 6-methoxypyridine-3-amine were dissolved in toluene (80 mL), and 16.1 g (50 mmol) of cesium carbonate, 1.3 g (1.5 mmol) of tris(dibenzylideneacetone)dipalladium(0), and 1.8 g (3.1 mmol) of 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene were added to the solution. The resulting mixture was heated and stirred for 72 hours at 90° C. The solvent was distilled off from the reaction mixture, water and ethyl acetate were added to the residue, and the mixture was filtered. The filtrate was extracted with ethyl acetate, and the organic phase was dried and concentrated. The residue was purified by column chromatography (ethyl acetate:n-hexane=1:4 to 1:1), and thus 6.8 g of the title compound was obtained as a pale yellow viscous product (yield: 96%).

Provenance & Evidence