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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 37, 2007 - Issue 11
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Original Articles

Practical Synthesis of 4‐Fluoro‐2‐(methylthio)benzylamine and the Corresponding Sulfone and Sulfonamide

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Pages 1887-1897 | Received 19 Oct 2006, Published online: 30 Jun 2007

References

  • Hazuda , D. J. , Anthony , N. J. , Gomez , R. P. , Jolly , S. M. , Wai , J. S. , Zhuang , L. , Fisher , T. E. , Embrey , M. W. , Guare , J. P. Jr. , Egbertson , M. S. , Vacca , J. P. , Huff , J. R. , Felock , P. J. , Witmer , M. V. , Stillmock , K. A. , Danovich , R. , Grobler , J. , Miller , M. D. , Espeseth , A. S. , Jin , L. , Chen , I.‐W. , Lin , J. , Kassahun , K. , Ellis , J. D. , Wong , B. K. , Xu , W. , Pearson , P. G. , Schleif , W. A. , Cortese , R. , Emini , E. , Summa , V. , Holloway , M. K. and Young , S. D. 2004 . A naphthyridine carboxamide provides evidence for discordant resistance between mechanistically identical inhibitors of HIV‐1 integrase . Proc. Natl. Acad. Sci. USA , 101 : 11233 – 11238 .
  • Hazuda , D. J. , Young , S. D. , Guare , J. P. , Anthony , N. J. , Gomez , R. P. , Wai , J. S. , Vacca , J. P. , Handt , L. , Motzel , S. L. , Klein , H. J. , Dornadula , G. , Danovich , R. M. , Witmer , M. V. , Wilson , K. A. A. , Tussey , L. , Schleif , W. A. , Gabryelski , L. S. , Jin , L. , Miller , M. D. , Casimiro , D. R. , Emini , E. A. and Shiver , J. W. 2004 . Integrase inhibitors and cellular immunity suppress retroviral replication in rhesus macaques . Science , 305 : 528 – 532 .
  • Parham , W. E. , Bradsher , C. K. and Edgar , K. J. 1981 . o‐Benzoylbenzoic acids by the reaction of lithium 2‐lithiobenzoates with acid chlorides: A contribution to the chemistry of alizarin and podophyllotoxin . J. Org. Chem. , 46 : 1057 – 1061 .
  • Parham , W. E. and Bradsher , C. K. 1982 . Aromatic organolithium reagents bearing electrophilic groups: Preparation by halogen lithium exchange . Acc. Chem. Res. , 15 : 300 – 305 .
  • Beak , P. and Sniekus , V. 1982 . Directed lithiation of aromatic tertiary amides: An evolving synthetic methodology for polysubstituted aromatics . Acc. Chem Res. , 15 : 306 – 312 .
  • Egbertson , M. S. , Naylor , A. M. , Hartman , G. D. , Cook , J. J. , Gould , R. J. , Holahan , M. A. , Lynch , J. J. Jr. , Lynch , R. J. , Stranieri , M. T. and Vassallo , L. M. 1994 . Non‐peptide fibrinogen receptor antagonists, 3: Design and discovery of a centrally constrained inhibitor . Bioorg. Med. Chem. Lett. , 4 : 1835 – 1840 . For 2‐bromobenzoic acids, which could be deprotonated and ortho‐lithiated with alkyl lithium at comparable rates, we reasoned that complete formation of magnesium benzoate prior to lithiation would suppress the quenching of the ortho‐anion by residual carboxylic acid. This is analogous to the conditions employed in
  • Egbertson , M. S. , Hartman , G. D. , Gould , R. J. , Bednar , R. A. , Cook , J. J. , Gaul , S. L. , Holahan , M. A. , Libby , L. A. , Lynch , J. J. Jr. , Lynch , R. J. , Sitko , G. R. , Stranieri , M. T. and Vassallo , L. M. 1996 . Nonpetide GPIIB/IIIA inhibitors, 10: Centrally constrained alpha‐sulfonamides are potent inhibitors of platelet aggregation . Bioorg. Med. Chem. Lett. , 6 : 2519 – 2524 .
  • March , J. 1992 . Advanced Organic Chemistry: Reactions, Mechanisms, and Structure , 4th edn. 1222 New York : John Wiley and Sons .
  • Sato , T. and Nakamura , A. A mixture of 2‐fluoro‐4‐methoxybenzonitrile (56%) and 4‐fluoro‐2‐methoxybenzonitrile (38%) was obtained from the treatment of 2,4‐difluorobenzonitrile with sodium methoxide in methanol, a polar, protic solvent . Patent JP 09143139 . 1997 .

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