Aniline → (R)-N-[2-Chloro-4-(N-phenylcarbamoyl)phenyl]-2-hydroxy-2methyl-3,3,3-trifluoropropanamide

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Reaction Conditions

Reaction Steps

A mixture of (R)-N-(2-chloro-4-iodophenyl)-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide (Example 197) (0.35 g), aniline (0.117 ml), tributylamine (0.232 ml) and dichlorobis-(triphenylphosphine)palladium(II) (0.009 g) was heated at 100° C. under an atmosphere of carbon monoxide for 4 hours. Ethyl acetate (10 ml) was added and the mixture was washed with water and brine then was dried. Volatile material was removed by evaporation and the residue was purified by chromatography on a silica gel Mega Bond Elut column eluting with 5-50% ethyl acetate/hexane followed by passing through a Varian Isolute SCX column to give the title compound (0.17 g) as a solid. NMR: 1.6 (s, 3H), 7.1 (t, 1H), 7.35 (t, 2H), 7.75 (d, 2H), 7.92 (s, 1H), 7.98 (dd, 1H), 8.12 (s, 1H), 8.2 (d, 1H), 9.8 (s, 1H), 10.26 (brs, 1H); MS (ESP−): 386.

Provenance & Evidence