Cesium carbonate → HCID 86682404, compound

Participants

Reaction Steps

To a solution of 5-[(6-methoxypyridin-3-yl)methyl]-1,2-dihydro-3H-benzo[e]isoindol-3-one (0.050 g, 0.16 mmol) in 1 mL of dioxane under an atmosphere of nitrogen was added 2-bromo-3-(trifluoromethyl)pyridine (0.037 g, 0.16 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.014 g, 0.025 mmol), cesium carbonate (0.075 g, 0.23 mmol), and tris[dibenzylideneacetone]dipalladium (0) (7.5 mg, 0.0082 mmol). The mixture was irradiated in a microwave reactor at 140° C. for 1.5 hr, cooled to ambient temperature, and diluted with ethyl acetate. The organic solution was washed with water, dried with sodium sulfate, filtered, and concentrated in vacuo. The residue was purified via preparative reverse phase HPLC to provide the title compound that gave a proton NMR spectra consistent with theory and a mass ion (ES+) of 450.1423 for [M+H]+ [calc'd for C25H19F3N3O2, [M+H]+=450.1424]: 1H NMR (400 MHz, CDCl3) δ 8.79-8.77 (m, 1H), 8.20-8.12 (m, 3H), 7.95-7.91 (m, 1H), 7.76 (s, 1H), 7.69-7.62 (m, 2H), 7.52-7.44 (m, 2H), 6.71 (d, J=8.6 Hz, 1H), 5.34 (s, 2H), 4.46 (s, 2H), 3.94 (s, 3H) ppm.

Provenance & Evidence