Cesium carbonate → Methyl cis(+/-)-5-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)thiophene-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

A suspension of ethyl 5-bromothiophene-2-carboxylate obtained in Example (244a) (100 mg, 0.45 mmol), benzyl cis(±)-(3-methoxypiperidin-4-yl)-carbamate obtained in Example (40b) (143 mg, 0.54 mmol), palladium acetate (10 mg, 0.05 mmol), BINAP (28 mg, 0.05 mmol) and cesium carbonate (206 mg, 0.63 mmol) in toluene was stirred at 110° C. for 39 hours. The reaction solution was diluted with ethyl acetate, washed with water and brine, and then dried over anhydrous magnesium sulfate. Following filtration, the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=2/1) to obtain 110 mg of the title compound as a yellow oily substance (60%).

Provenance & Evidence