Triethylamine → Fluxapyroxad

Participants

Reaction Conditions

Reaction Steps

In an autoclave, 2-(3,4,5-trifluorophenyl)aniline (5.29 g, 23.7 mmol), triethylamine (1.20 g, 11.8 mmol), palladium chloride (86 mg, 0.47 mmol), anhydrous potassium carbonate (6.55 g, 47.4 mmol) and 2,2-dimethyl-1,3-bis(diphenylphosphino)propane (313 mg, 0.71 mmol) were added to a solution of 4-bromo-3-difluoromethyl-1-methylpyrazole (5.00 g, 23.7 mmol) in acetonitrile (100 ml). The autoclave was flushed three times with 9 bar of nitrogen and then 3 times with 10 bar of carbon monoxide. The reaction mixture was stirred under a carbon monoxide pressure of 9 mbar at an external temperature of 130° C. for 20 h. The red-brown suspension obtained after cooling and venting was filtered, and the filtrate was freed from volatile components under reduced pressure. The residue was taken up in a mixture of tetrahydrofuran (60 ml) and methyl tert-butyl ether (MTBE, 60 ml), washed twice with hydrochloric acid (5% strength, in each case 40 ml) and once with water (30 ml), dried over sodium sulfate and filtered, and the solvent was removed under reduced pressure. The residue was triturated with diisopropyl ether (20 ml), and the solid was filtered off and dried under reduced pressure. 5.20 g (yield 54%) of N-(2-(3,4,5-trifluorophenyl)phenyl)-3-difluoromethyl-1-methylpyrazole-4-carboxamide were isolated in a purity of 93%, according to HPLC analysis (Merck Chromolith SpeedROD RP-18e column, 50×4.6 mm; gradient: acetonitrile/water with 0.1% trifluoroacetic acid, 7 min from 10% to 95% acetonitrile).

Provenance & Evidence