Sodium Carbonate → N-[4-methoxy-3-(4-methyl-1-piperazinyl)phenyl]-5-(4-pyridyl)furan-2-carboxamide

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Reaction Steps

5-bromo-N-[4-methoxy-3-(4-methyl-1-piperazinyl)phenyl]furan-2-carboxamide (0.3 g;0.76 mmol) was stirred with 4-pyridylboronic acid (0.094 g;0.76 mmol), tetrakis(triphenylphosphine)palladium(0) (0.045 g;5 mol %) and anhydrous sodium carbonate (0.089 g;0.84 mmol) in water (14 ml) and DME (14 ml) and the whole heated at reflux under Ar (18 hours). The reaction mixture was poured into 10% Na2CO3 (aq) (30 ml) and extracted into CHCl3. The organic extracts were combined, dried over Na2 SO4, filtered and the filtrate evaporated in vacuo to a brown oil which crystallised on standing. The brown solid was purified by flash silica-gel chromatography and eluted with 3%MeOH/CHCl3 to yield the title compound as a lemon solid (0.22 g;74%), mp=157°-159° C.

Provenance & Evidence