Cesium carbonate → HCID 59276196, compound

Participants

Reaction Conditions

Reaction Steps

4-(5-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino)benzonitrile. To an orange solution of 5-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-amine (2.00 g, 9.39 mmol) in dioxane (100 mL) was added 4-iodobenzonitrile (4.30 g, 18.78 mmol), cesium carbonate (6.12 g, 18.78 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (1.086 g, 1.878 mmol) and tris(dibezylideneacetone)palladium (0.903 g, 0.986 mmol) at room temperature under nitrogen. The reaction mixture was heated at 100° C. for 18 h under nitrogen. Upon completion of the reaction, as indicated by LCMS, the reaction mixture was poured into water/brine, and extracted with ethyl acetate several times. The combined organic layers were dried over anhydrous magnesium sulfate and concentrated. The crude mixture was triturated with ethyl acetate to give the title compound as a brownish yellow solid (0.565 g, 20% yield). 1H NMR (400 MHz, DMSO-d6) δ (ppm) 10.55 (s, 1H), 7.89-7.87 (m, 2H), 7.77-7.75 (m, 2H), 7.71-7.69 (m, 1H), 7.58-7.54 (m, 1H), 7.49-7.46 (m, 1H); MS (ESI) m/z 315.14 [M+1]+

Provenance & Evidence