Potassium Carbonate → (+,-) Trans Propane-2-sulfonic Acid (2-biphenyl-4-yl-cyclopentyl)-amide

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

(+,−) Trans propane-2-sulfonic acid [2-(4-iodo-phenyl)-cyclopentyl]-amide (58 mg, 0.15 mmol, prepared in example 2) and phenylboronic acid (22 mg, 0.18 mmol) were dissolved in 20 mL of n-propanol and 25 mg (0.18 mmol)of potassium carbonate in 5 mL of water added. A catalytic amount of palladium acetate is added (2 mg) and the mixture refluxed at 90° C. for 4 hours. The reaction is filtered, rinsed with ethyl acetate. The filtrate is diluted with ethyl acetate and washed with saturated sodium bicarbonate (3×30 mL) and brine (1×30 mL). The organic phase is dried over sodium sulfate, filtered and concentrated in vacuo to a crude solid which is purified by reverse phase chromatography (Vydac C18 column with a CH3CN gradient of 5→55% over 2 hours with a flow rate of 20 mL/min). The fractions were freeze-dried to give 34 mg (68%) of the title compound. The NMR was consistent with. the assigned structure.

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