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Volumn 37, Issue 11, 2007, Pages 1887-1897

Practical synthesis of 4-fluoro-2-(methylthio)benzylamine and the corresponding sulfone and sulfonamide

Author keywords

Lithiation; Nucleophilic aromatic substitution; Sulfonamide; Sulfone; Thiol

Indexed keywords

2 AMINOMETHYL 5 FLUORO N,N DIMETHYLBENZENESULFONAMIDE; 4 FLUORO 2 METHYLSULFONYLBENZYLAMINE; 4 FLUORO 2 METHYLTHIOBENZYLAMINE; AROMATIC COMPOUND; BENZENESULFONIC ACID DERIVATIVE; BENZONITRILE; BENZYLAMINE; BROMOBENZOIC ACID DERIVATIVE; DIMETHYL DISULFIDE; INTEGRASE INHIBITOR; MESYLIC ACID DERIVATIVE; METHANETHIOL; SOLVENT; SULFONAMIDE; SULFONE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 34250303828     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910701319221     Document Type: Article
Times cited : (6)

References (9)
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    • 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.; Young, S. D. A naphthyridine carboxamide provides evidence for discordant resistance between mechanistically identical inhibitors of HIV-1 integrase. Proc. Natl. Acad. Sci. USA 2004, 101, 11233-11238;
    • (a) 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.; Young, S. D. A naphthyridine carboxamide provides evidence for discordant resistance between mechanistically identical inhibitors of HIV-1 integrase. Proc. Natl. Acad. Sci. USA 2004, 101, 11233-11238;
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    • o-Benzoylbenzoic acids by the reaction of lithium 2-lithiobenzoates with acid chlorides: A contribution to the chemistry of alizarin and podophyllotoxin
    • (a) Parham, W. E.; Bradsher, C. K.; Edgar, K. J. 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. 1981, 46, 1057-1061;
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    • Parham, W.E.1    Bradsher, C.K.2    Edgar, K.J.3
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    • Aromatic organolithium reagents bearing electrophilic groups: Preparation by halogen lithium exchange
    • (b) Parham, W. E.; Bradsher, C. K. Aromatic organolithium reagents bearing electrophilic groups: Preparation by halogen lithium exchange. Acc. Chem. Res. 1982, 15, 300-305;
    • (1982) Acc. Chem. Res , vol.15 , pp. 300-305
    • Parham, W.E.1    Bradsher, C.K.2
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    • Directed lithiation of aromatic tertiary amides: An evolving synthetic methodology for polysubstituted aromatics
    • (c) Beak, P.; Sniekus, V. Directed lithiation of aromatic tertiary amides: An evolving synthetic methodology for polysubstituted aromatics. Acc. Chem Res. 1982, 15, 306-312.
    • (1982) Acc. Chem Res , vol.15 , pp. 306-312
    • Beak, P.1    Sniekus, V.2
  • 6
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    • 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; (a) 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.; Vassallo, L. M. Non-peptide fibrinogen receptor antagonists, 3: Design and discovery of a centrally constrained inhibitor. Bioorg. Med. Chem. Lett. 1994, 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; (a) 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.; Vassallo, L. M. Non-peptide fibrinogen receptor antagonists, 3: Design and discovery of a centrally constrained inhibitor. Bioorg. Med. Chem. Lett. 1994, 4, 1835-1840;
  • 9
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    • Sato, T, 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
    • Sato, T.; 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.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.