Sodium Carbonate → {1-[4-(6-Oxo-8-phenyl-1,6-dihydro-9-oxa-1,2-diaza-cyclopenta[a]naphthalen-7-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

To a microwave vial were added 7-iodo-8-phenyl-1H-9-oxa-1,2-diaza-cyclopenta[a]naphthalen-6-one (100 mg, 0.257 mmol), {1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (115 mg, 0.308 mmol), sodium carbonate solution (2 M in water, 1 mL), tetrakis(triphenylphosphine)palladium(0) (44.5 mg, 0.039 mmol) and DME (3 mL). The reaction mixture was purged using nitrogen and heated in a microwave reactor at 125° C. for 1 hour. Further portions of {1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (50 mg, 0.134 mmol) and tetrakis(triphenylphosphine)palladium(0) (20 mg, 0.017 mmol) were added and the mixture was heated in a microwave reactor at 125° C. for a further 1 hour. The reaction mixture was partitioned between EtOAc and water and the resulting biphasic mixture was separated. The aqueous phase was extracted with EtOAc and the combined organic phase was washed with water and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The resultant residue was subjected to flash chromatography (SiO2, gradient 30 to 70% EtOAc in cyclohexane) to afford the title compound (55.1 mg, 42%) as a yellow gum. LCMS (Method H): RT=3.95 min, [M+H]+=508.

Provenance & Evidence