Sodium ethanethiolate → (R)-N-[2-Chloro-4-(ethylsulphanyl)phenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide

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Reaction Conditions

Reaction Steps

Copper (I) chloride (0.5 g) and sodium ethanethiolate (0.54 g) were added sequentially to a deoxygenated solution of (R)-N-(2-chloro-4-iodophenyl)-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide (Example 197) (2.0 g) in quinoline (6 ml) and pyridine (1.5 ml). The mixture was heated to 200° C. under argon for 18 hours, cooled dissolved in ethyl acetate (200 ml), washed with dilute aqueous hydrochloric acid (2×100 ml) and brine (2×50 ml) and then dried. Volatile material was removed by evaporation and the residue was purified by chromatography on silica gel eluting with 10-40% ethyl acetate/iso-hexane to give the title compound as a gum (1.4 g). NMR (CDCl3): 1.29 (t, 3H), 1.57 (s, 3H), 2.91 (q, 2H), 3.69 (s, 1H), 7.24 (d, 1H), 7.35 (s, 1H), 8.24 (d, 1H), 8.77 (s, 1H); MS (ESP−): 326.

Provenance & Evidence