Efficient Synthesis of 5-(Bromomethyl)-and 5-(Aminomethyl)-1-THP-Indazole

Journal of Organic Chemistry

Volumn 62, Issue 16, 1997, Pages 5627-5629

  Sun, Jung Hui ^a   Teleha, Christopher A ^a   Yan, Jia Sheng ^a   Rodgers, James D ^a   Nugiel, David A ^a  

^a DUPONT COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

5 (AMINOMETHYL) 1 TETRAHYDROPYRANYLINDAZOLE; 5 (BROMOMETHYL) 1 TETRAHYDROPYRANYLINDAZOLE; ANTIVIRUS AGENT; PROTEINASE INHIBITOR; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; MOLECULAR MODEL; ORGANIC CHEMISTRY; PROTEINASE INHIBITION; STRUCTURE ACTIVITY RELATION; VIRUS INHIBITION;

EID: 0030860705     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970375b     Document Type: Article

References (12)

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4. Elguero, J. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon Press: New York, 1984; Vol. 5, p 167. For more recent examples see: Ruchardt, C.; Hassman, V. Liebigs Ann. Chem. 1980, 908. Dell'Erba, C.; Novi, M.; Petrillo, G.; Tavani, C. Tetrahedron 1992, 48, 325.
5. Elguero, J. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon Press: New York, 1984; Vol. 5, p 167. For more recent examples see: Ruchardt, C.; Hassman, V. Liebigs Ann. Chem. 1980, 908. Dell'Erba, C.; Novi, M.; Petrillo, G.; Tavani, C. Tetrahedron 1992, 48, 325.
6. Rodgers, J. D.; Johnson, B. L.; Wang, H.; Greenberg, R. A.; Erickson-Viitanen, S.; Klabe, R. M.; Cordova, B. C.; Rayner, M. M.; Lam, G. N.; Chang, C.-H. BioMed. Chem. Lett. 1996, 6, 2919.
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9. Bartsch, R. A.; Yang, I.-W. J. Heterocycl. Chem. 1984, 21, 1063. Phase-transfer-promoted indazole formation was also observed as a byproduct in the synthesis of biarenes. See: Beadle, J. R.; Korzeniowski, S. H.; Rosenberg, D. E.; Garcia-Slanga, B. J.; Gokel, G. W. J. Org. Chem. 1984, 49, 1594.
10. Bartsch, R. A.; Yang, I.-W. J. Heterocycl. Chem. 1984, 21, 1063. Phase-transfer-promoted indazole formation was also observed as a byproduct in the synthesis of biarenes. See: Beadle, J. R.; Korzeniowski, S. H.; Rosenberg, D. E.; Garcia-Slanga, B. J.; Gokel, G. W. J. Org. Chem. 1984, 49, 1594.
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12. 3/MeOH and treating the subsequent 5-(hydroxymethyl)-1H-indazole with 48% HBr in 42% overall yield.