反应详情

温度

90 °C

(+,−) 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.

1. filtrationThe reaction is filtered
2. washrinsed with ethyl acetate
3. additionThe filtrate is diluted with ethyl acetate
4. washwashed with saturated sodium bicarbonate (3×30 mL) and brine (1×30 mL)
5. dry with materialThe organic phase is dried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated in vacuo to a crude solid which
8. customis 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)
9. customThe fractions were freeze-dried