1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → N-(5-((3R)-3-((tert-butyl(dimethyl)silyl)oxy)-1-pyrrolidinyl)-2-pyridinyl)-9-cyclopentyl-8-fluoro-9H-pyrido[4',3':4,5]pyrrolo[2,3-d]pyrimidin-2-amine

Participants

Reaction Conditions

Reaction Steps

A 10 mL reaction vessel was charged with compound 245 (75.0 mg, 276 mmol), (R)-5-(3-(t-butyldimethylsilyloxy)pyrrolidin-1-yl)-2-chloropyridine (86.5 mg, 276 mmol), tris(dibenzylideneacetone)dipalladium (0) (19.0 mg, 20.7 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene (24.0 mg, 41.5 mmol), sodium t-butoxide (53.1 mg, 553 mmol), and dioxane (1.5 mL). The reaction was heated with microwave energy (300 W) for 2 hours at 120° C. in the resulting solution was added to ethyl acetate (40 mL) and washed with water (30 mL) followed by brine (30 mL). The organic phase was dried (MgSO4) and evaporated to give an orange oil. Silica gel chromatography (gradient elution 35% ethyl acetate in hexanes) afforded compound 278 as a yellow solid (59 mg, 39%)

Provenance & Evidence