Controlled derivatization of polyhalogenated quinolines utilizing selective cross-coupling reactions

Tetrahedron Letters

Volumn 49, Issue 19, 2008, Pages 3137-3141

  Brad Nolt, M ^a   Zhao, Zhijian ^a   Wolkenberg, Scott E ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 BROMO 7 CHLORO 6 IODOQUINOLINE; 6 BROMO 4 CHLORO 3 IODOQUINOLINE DERIVATIVE; 6 BROMO 4 HYDROXYQUINOLINE DERIVATIVE; PALLADIUM; POLYHALO DERIVATIVE; QUINOLINE DERIVATIVE; QUINOLINOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CROSS COUPLING REACTION; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; HALOGENATION;

EID: 41649088596     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.03.040     Document Type: Article

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20. Not surprisingly, double arylation of 15a was also possible by heating at 160 °C for 10 min with an excess of arylboronic acid.
21. Deprotection (TFA) of the Boc-protected piperidine nitrogen was required in parallel, and was technically non-demanding.
22. +) 379.9603, found 379.9604.
23. +) 394.9712, found 394.9716.
24. 3 system.
25. 2Pd(dppf) was added to the reaction mixture.
26. 3 in a 2-5 mL Biotage microwave reaction vial containing a magnetic stir bar. The vial was capped and heated in a Biotage Optimizer reactor cavity for 15 min at 90 °C, after which the vessel was rapidly cooled to 40 °C by the unit. The organic phase was separated, evaporated under reduced pressure, and purified by flash chromatography (4-10% EtOAc/hexanes) to provide 23 (77 mg, 77%).
27. Manuscript in preparation.