Cesium carbonate → HCID 178428287, compound

Participants

Reaction Conditions

Reaction Steps

cis-6-(5-(4-Hydroxycyclohexylamino)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino)-1,4-dimethylindoline-2,3-dione. A mixture of 6-bromo-1,4-dimethylindoline-2,3-dione (0.34 g, 1.338 mmol), cis-4-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-5-ylamino)cyclohexanol (0.446 g, 1.804 mmol), cesium carbonate (1.308 g, 4.01 mmol), tris(dibenzylideneacetone) dipalladium(0) (0.245 g, 0.268 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.310 g, 0.535 mmol) in 1,4-dioxane (6 mL) was degassed for 2 min and then stirred at 90° C. for 17 h. The cooled reaction solution was filtered through Celite and the filter cake was washed with dichloromethane and methanol. The solvent was removed under reduced pressure. Purification by column chromatography (eluting with 0-10% methanol in dichloromethane) provided the title compound as a yellow solid (0.22 g, 39.1% yield). MS (ESI) m/z 421.5 [M+H]+.

Provenance & Evidence