Ethanol → 3-chloro-N-[4-(3'-cyano-biphenyl-4-yl)-1-cyclopropylmethyl-piperidin-4-ylmethyl]-4-fluoro-benzenesulfonamide

To a flask containing 3-chloro-N-[1-cyclopropylmethyl-4-(4-iodo-phenyl)-piperidin-4-ylmethyl]-4-fluorobenzenesulfonamide (0.047 g, 0.04 mmol) was added Pd(PPh3)4 (0.005 g, 0.004 mmol, 10 mol %), 3-cyanophenylboronic acid (0.01 g, 0.06 mmol, 1.5 eq.) and Na2CO3 (0.106 g, 1 mmol). The mixture was suspended in toluene (1.5 mL), EtOH (0.75 mL) and H2O (0.5 mL) and heated to 80° C. for 18 h. The reaction mixture was cooled to room temperature and partitioned between ethyl acetate (5 mL) and saturated Na2CO3 (5 mL). The organic layer was washed with saturated Na2CO3 (3×5 mL), saturated brine (2×5 mL), dried over anhydrous sodium sulfate, filtered and concentrated to give a brown solid which was purified by HPLC to give 3-chloro-N-[4-(3′-cyano-biphenyl-4-yl)-1-cyclopropylmethyl-piperidin-4-ylmethyl]-4-fluoro-benzenesulfonamide (0.097 g, 45%). MS (ESI): 538.2/540.2.

1. custompartitioned between ethyl acetate (5 mL) and saturated Na2CO3 (5 mL)
2. washThe organic layer was washed with saturated Na2CO3 (3×5 mL), saturated brine (2×5 mL)
3. dry with materialdried over anhydrous sodium sulfate
4. filtrationfiltered
5. concentrationconcentrated
6. customto give a brown solid which
7. customwas purified by HPLC

ORDレコード

ord-91067b2ceb104f6bafff75c6040098eb

出典データセット

uspto-grants-2005_05

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06887889B2