3H- and 14C-labelling of the aromatase inhibitor ZK 138723

Gay, Jamie C.; Strehlke, P.

doi:10.1002/(sici)1099-1344(199604)38:4<349::aid-jlcr849>3.0.co;2-i

Cited by 1 publication

(2 citation statements)

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“…In general, electron rich aromatics can give slightly depressed yields, and certain heterocycles including imidazoles, pyrrazoles, and thiophenes [38,48] have been reported to give low yields with either method.…”

Section: [ 14 C]methyl Iodidementioning

confidence: 99%

“…Conversion to the furan was accomplished in three steps by conversion to the acid chloride then treatment with freshly prepared diazomethane to give the diazoketone (47). Acid catalyzed intramolecular cyclization gave 4-bromo-[3-14 C]benzofuran-3-one (48) in 60% overall yield [69]. The synthesis of [ 14 C]GR-151004 (50) was completed by olefination to give the benzofuran (49), then in three completed in three steps utilizing a palladium catalyzed cross-coupling reaction to construct the biphenyl bond.…”

Section: Diazoketones In Labelled Synthesismentioning

confidence: 99%

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Recent Advances in the Design and Synthesis of Carbon-14 Labelled Pharmaceuticals from Small Molecule Precursors

McCarthy

2000

CPD

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Over the past decade, the increased chemical complexity of new drug candidates has resulted in a parallel need to develop innovative syntheses of carbon-14 labelled pharmaceuticals. Faced with short time-lines and a limited number of labelled precursors, radiochemists have addressed this challenge by developing new reagents and adapting existing technology to labelled syntheses. Selected examples from the recent radiochemical literature illustrate some of the creative strategies used to rapidly solve these synthetic challenges. Examples describing the handling and use of common small molecule reagents, such as carbon-14 labelled carbon dioxide, methyl iodide, cyanide, acetic acids, sulfur and phosphorous stabilized ylides for the synthesis of labelled steroids, prostanoids, nucleosides, pyridines, quinolines, benzazepines and other heterocycles are presented. Several general strategies for radiolabelling are also discussed including the degradation strategy for accessing necessary intermediates and precursors, the radiolabelling of aromatic substrates, transition metal mediated cross-couplings, and the use of chiral auxiliaries for the enantioselective syntheses of radiolabelled pharmaceuticals.

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Section: [ 14 C]methyl Iodidementioning

confidence: 99%

Section: Diazoketones In Labelled Synthesismentioning

confidence: 99%