Cesium carbonate → HCID 178513661, compound

Participants

Reaction Conditions

Reaction Steps

tert-Butyl cis-4-(2-(4-cyanophenylamino)-[1,2,4]triazolo[1,5-a]pyridin-5-ylamino)cyclohexylcarbamate. To an orange solution of 4-(5-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino)benzonitrile (0.200 g, 0.637 mmol) in dioxane (10 mL) was added tert-butyl cis-4-aminocyclohexylcarbamate (0.273 g, 1.273 mmol), cesium carbonate (0.415 g, 1.273 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.074 g, 0.127 mmol) and tris(dibezylideneacetone)palladium (0.061 g, 0.0669 mmol) at room temperature under nitrogen. The reaction mixture was heated at 100° C. for 1 h under nitrogen. Upon completion of the reaction, as indicated by LCMS, the reaction mixture was poured into brine, and extracted with ethyl acetate several times. The combined organic layers were dried over anhydrous magnesium sulfate and concentrated. The crude mixture was purified by column chromatography (eluting with 0-80% ethyl acetate in hexanes) to give the title compound as a tan solid (0.082 g, 29% yield). 1H NMR (400 MHz, DMSO-d6) δ (ppm) 10.22 (s, 1H), 7.89 (d, 2H, J=8 Hz), 7.73 (d, 2H, J=8 Hz), 7.46 (t, 1H, J=8 Hz), 6.81 (d, 1H, J=8 Hz), 6.25 (d, 1H, J=8 Hz), 6.02 (d, 1H, J=8 Hz), 3.71-3.64 (m, 1H), 3.56-3.34 (m, 1H), 1.90-1.73 (m, 4H), 1.66-1.61 (m, 4H), 1.40 (s, 9H); MS (ESI) m/z 448.53 [M+1]+.

Provenance & Evidence