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

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Reaction Steps

5-bromo-N-[4-methoxy-3-(4-methyl-1-piperazinyl)phenyl]thiophene-2-carboxamide (0.31 g;0.76 mmol) was stirred with 4-pyridylboronic acid (0.093 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 gum. The gum was purified by flash silica-gel chromatography and eluted with 4%MeOH/CHCl3 to yield a yellow, semi-solid residue which was triturated with acetone/Et2O. The solid that formed was collected by filtration and dried in vacuo to yield the tide compound as a yellow solid (0.2 g;65%), mp=191-194° C.

Provenance & Evidence