Potassium Acetate → Tert-butyl 4-(3-(5-(6-methoxy-1-oxoisoindolin-2-yl)furan-2-carboxamido)pyridin-4-yl)piperazine-1-carboxylate

Participants

Reaction Steps

A mixture of tert-butyl 4-(3-(5-bromofuran-2-carboxamido)pyridin-4-yl)piperazine-1-carboxylate (1.3, 100 mg, 0.20 mmol), the 6-methoxy-2,3-dihydro-isoindol-1-one,(1.4, 1.2 equivalent), Tris(dibenzylideneacetone) dipalladium(0) (20 mg, 0.02 mmol), Xantphos (26 mg, 0.04 mmol), Potassium acetate (139 mg, 0.66 mmol) in 5 ml of Dioxane was heated to 85° C. for 16 hours. Resulting suspension was diluted with ethyl acetate and passed through a celite filter to remove insoluble solid. Organic layer was concentrated in vacuo. The crude compound was purified by Prep-LC to yield compound, tert-butyl 4-(3-(5-(6-methoxy-1-oxoisoindolin-2-yl)furan-2-carboxamido)pyridin-4-yl)piperazine-1-carboxylate (1.5). HPLC-MS tR=3.84 min (UV254 nm); Mass calculated for formula C28H31N5O6, 533.23; observed LCMS m/z 534.20(M+H).

Provenance & Evidence