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The radiolabeled syntheses of JV 485, a herbicide candidate for winter wheat
Author(s) -
Maxwell Brad D.
Publication year - 2000
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/1099-1344(200006)43:7<645::aid-jlcr349>3.0.co;2-6
Subject(s) - chemistry , yield (engineering) , trifluoromethyl , amide , ring (chemistry) , desmethyl , medicinal chemistry , stereochemistry , pyrazole , organic chemistry , metabolite , biochemistry , alkyl , materials science , metallurgy
JV 485 [ 14 C‐Ph] and JV 485 [ 14 C‐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 (1) of an aromatic methyl group to a carboxylic acid. The 14 C radiolabeled syntheses of two isolated metabolites of JV 485 were also completed. Preparation of the JV 485 [phenyl‐ 14 C(U)] amide was completed in 62% yield from 2‐chloro‐5‐[4‐bromo‐1‐methyl‐5‐trifluoromethyl)‐1H‐pyrazol‐3‐yl]‐4‐fluorobenzoic acid [ring‐ 14 C(U)], 9 . Preparation of the JV 485 [phenyl‐ 14 C(U)] desmethyl acid 13 was accomplished in 18% overall yield in four steps from 3‐(4‐chloro‐2‐fluoro‐5‐methylphenyl [ring‐ 14 C(U)])‐5‐(trifluoromethyl)‐1H‐pyrazole, 4 . Copyright © 2000 John Wiley & Sons, Ltd.