The radiolabeled syntheses of JV 485, a herbicide candidate for winter wheat

JV 485 [C-14-Ph] and JV 485 [C-14-Py] were synthesized in seven steps in 35 % and 44% overall yields, respectively, utilizing the same reaction schemes . The key step in each of the syntheses is a one pot Mid-Century Oxidation (I) of an aromatic methyl group to a carboxylic acid. The C-14 radiolabeled syntheses of two isolated metabolites of JV 485 were also completed. Prepa ration of the JV 485 [phenyl-C-14(U)] amide was completed in 62% yield from 2-chloro-5-14-bromo-1-methyl-5-trifluoromethyl)-1H-pyrazol-3-yl]-4-fluorob enzoic acid [ring-C-14(U)], (9) over bar. Preparation of the JV 485 [phenyl -C-14(U)] desmethyl acid <(13)over bar> was accomplished in 18% overall yie ld in four steps from 3-(4-chloro-2-fluoro-5-methylphenyl [ring-14C(U)])-5- (trifluoromethyl)1H-pyrazole, (4) over bar.