Dimethylformamide → HCID 69347256, compound

Participants

Reaction Conditions

Reaction Steps

880 mg (2.93 mmol) of trifluoro-methanesulfonic acid 4-tert-butyl-2-fluoro-phenyl ester and 1.13 g (5.86 mmol) of 2-(3-trifluoromethyl-phenyl) ethyl amine were dissolved in 15 ml DMF. Under argon at rt 19.7 mg (0.0.88 mmol) of palladium acetate and 36.2 mg (0.088 mmol) of dppp were added. The reaction mixture was evacuated and charged with carbon monoxide gas three times. The reaction mixture was heated to 80° C. under a carbon monoxide atmosphere for 1 h. Water was added and the reaction mixture was extracted twice with EtOAc. The combined organic layers were washed with 1N aqueous HCl solution, once with saturated aqueous NaCl solution, dried over sodium sulfate, filtered and the solvent was evaporated. The residue was purified by column chromatography (60 g silica gel; heptane/EtOAc 7:3) to yield 676 mg (63%) of 4-tert-butyl-2-fluoro-N-[2-(3-trifluoromethyl-phenyl)-ethyl]-benzamide as a yellow viscous oil. 1H NMR (DMSO-d6, 300 MHz): δ 8.28 (t, 1H), 7.60-7.55 (m, 4H), 7.47 (t, 1H), 7.28-7.22 (m, 2H), 3.51 (q, 2H), 2.94 (t, 2H), 1.27 (s, 9H).

Provenance & Evidence