Pyridine → (4-{4-[5-(4-Trifluoromethyl-benzenesulfonylamino)-pyridin-2-yl]-phenyl}-cyclohexyl)-acetic acid methyl ester

Participants

Reaction Steps

To a solution of 0.300 g (0.925 mmol) of {4-[4-(5-Amino-pyridin-2-yl)-phenyl]-cyclohexyl}-acetic acid methyl ester, and 8 mL of dichloromethane was added 0.112 mL (1.39 mmol) of pyridine, 0.271 g (1.11 mmol) of 4-Trifluoromethyl-benzenesulfonyl chloride and 0.004 g (0.0277 mmol) DMAP. The dark orange solution was stirred at r.t. for 4 h. The mixture was extracted with dichloromethane, then washed with water, 1 N HCl, and brine. Dried with Na2SO4. Purified on silica gel (EtOAc/Heptane, 9:1 to 6:4) to afford the title compound. 1H NMR (400 MHz, CHLOROFORM-d6) 0.99-1.10 (m, 2H) 1.34-1.46 (m, 2H) 1.71-1.82 (m, 5H) 2.14 (d, J=6.82 Hz, 2H) 2.39 (tt, J=−12.16, 3.25 Hz, 1H) 3.57 (s, 3H) 7.16 (d, J=8.34 Hz, 2H) 7.54 (dd, J=2.53, 1.77 Hz, 2H) 7.61 (d, J=8.34 Hz, 2H) 7.73 (d, J=8.34 Hz, 2H) 7.78 (d, J=8.08 Hz, 2H) 8.14 (dd, J=2.27, 1.01 Hz, 1′H).

Provenance & Evidence