Adapalene, CD-271, Differin, Differine

合成路线:The bromination of 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthoic acid methyl ester (I) with Br2 in dichloromethane gives the dibromo derivative (II),which is hydrogenated with tritium gas over Pd/C in THF containing TEA to yield the bis tritiated ester (III).Finally,ester (III) is hydrolyzed with NaOH in refluxing methanol to afford the target tritiated naphthoic acid.

参考文献标题:Novel tritium marked cpds.,its preparation and application for finding of retinoid nuclear receptors
文献作者:Shroot,B.; Darmon,M.(Laboratoires Galderma SA)
参考来源:CA 2021550; EP 0409740; FR 2649976; JP 1991063246; US 5073361; US 5149631


合成路线:Friedel-Crafts condensation of 4-bromophenol (I) with 1-adamantanol (II) in the presence of H2SO4 yielded the adamantyl phenol (III).Subsequent alkylation of the sodium phenoxide of (III) with iodomethane produced the methyl ether (IV).The Grignard reagent (V),prepared from aryl bromide (IV),was converted to the organozincate derivative,and then subjected to a nickel-catalyzed cross-coupling with methyl 6-bromo-2-naphthoate (VI) to furnish adduct (VII).The target carboxylic acid was finally obtained by saponification of the methyl ester (VII).
参考文献标题:Synthesis,structure-affinity relationships,and biological activities of ligands binding to retinoic acid receptor subtypes
文献作者:Charpentier,B.; Bernardon,J.M.; Eustache,J.; Millois,C.; Martin,B.; Michel,S.; Shroot,B.
参考来源:J Med Chem 1995,38(26),4993


产品链接: CAS No. 106685-40-9››