Copper(I) chloride (0.038 g) was added to a mixture of (R)-N-(2-chloro-4-mercaptophenyl)-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide (Example 210) (0.21 g), N-(4-iodobenzenesulphonyl)pyrrolidine (0.258 g) and sodium methoxide (0.042 g) in DMA (5 ml). The mixture was heated at 150° C. with stirring for 4 hours then cooled and the DMA removed by evaporation. Ethyl acetate (20 ml) and water (20 ml) was added and the mixture was filtered. The aqueous layer was extracted with ethyl acetate (3×20 ml) and the organic layers were combined and dried. Volatile material was removed by evaporation and the residue was purified on a silica gel Mega Bond Elut column, eluting with methanol/DCM 0-10% to give the title compound (0.16 g) as a solid. NMR (CDCl3): 1.75 (s, 3H), 1.75-1.85 (m, 4H), 3.2-3.3 (m, 4H), 4.0 (s, 1H), 7.2-7.3 (m, 2H), 7.4-7.45 (m, 1H), 7.6 (s, 1H), 7.7 (d, 2H), 8.45 (d, 1H), 9.15 (s, 1H); MS (ESP−): 507.
