Cesium carbonate → HCID 86726511, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-(2-chloro-4-((tetrahydro-2H-pyran-4-yl)oxy)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-N-methylbenzamide (1 equiv), 1-methyl-1H-pyrazol-5-amine (1 equiv), and cesium carbonate (3 equiv) in 1,4-dioxane (0.1 M) was degassed with N2 for 10 min. Then (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.2 equiv), tris(dibenzylideneacetone)dipalladium(0) (0.1 equiv), were added to this mixture. The mixture was stirred at 140° C. for 1.5 h. After cooling to room temperature the reaction mixture was purified using flash chromatography (0-100% ethyl acetate in hexane then 0-20% MeOH in DCM) to give the title compound (39.4% yield) as an off white solid. MS (ESI) m/z 578.5 [M+1]+.

Provenance & Evidence