1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → N-(1-(2-Chloropyridin-4-yl)piperidin-4-yl)-8-(3,4-difluorophenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine

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Reaction Steps

A suspension of 1-(2-chloropyridin-4-yl)piperidin-4-amine dihydrochloride (142 mg, 0.50 mmol) in dichloromethane was washed with 2 N NaOH, the aqueous layer extracted with dichloromethane, the combined organic layers dried over sodium sulfate and evaporated. The “free-base” residue was dissolved in dioxane (4 mL), 2-bromo-8-(3,4-difluorophenyl)-[1,2,4]triazolo[1,5-a]pyridine (prepared in analogy to example 66a-d) (170 mg, 0.55 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (23 mg, 8 mol %), tris(dibenzylideneacetone)dipalladium chloroform complex (21 mg, 4 mol %) and sodium phenoxide (87 mg, 0.75 mmol) were added, Ar was bubbled through the reaction mixture for 5 minutes and then irradiated at 130° C. in the microwave for 1 hour. The crude material was purified by flash chromatography (silica-NH2, 20 g, 0 to 100% ethyl acetate in heptane). The title compound was obtained as a yellow solid (103 mg, 47%).

Provenance & Evidence