254
R. Liu et al.
130.080, 132.889, 133.072, 133.866, 144.706. HRMS: calcd. for C13H9N3O2:
230.0611; found: 230.0609.
ACKNOWLEDGMENT
This work was partially supported by the National Natural Science Foundation
of China (Grants 20472062 and 20672079) and the Natural Science Foun-
dation of Jiangsu Province (No. BK2006048).
REFERENCES
1. Elguero, J. Comprehensive Heterocyclic Chemistry; Katritzky, A. R. and
Rees, C. W., Eds.; Pergamon Press: New York, 1984 Vol. 5, p. 167.
2. (a) Bistochi, G. A.; De Meo, G.; Pedini, M.; Ricci, A.; Brouilhet, H.; Bucherie, S.;
Rabaud, M.; Jacquignon, P. N-substituted ethyl-1H-indazole-3-carboxylate and 1H-
indazole-3-hydroxamic acids. Farmaco Ed. Sci. 1981, 36, 315; (b) Picciola, G.;
Ravenna, F.; Carenini, G.; Gentili, P.; Riva, M. Heterocyclic compounds containing
a 4-aminophenylalkanoic acid moiety which have potential antiinflammatory
activity. IV. 2-Phenyl-2H-indazole derivatives. Farmaco Ed. Sci. 1981, 36, 1037.
3. Keppler, B. K.; Hartmann, M. New tumor-inhibiting metal complexes. Chemistry
and antitumor properties. Met.-Based Drugs 1994, 1 (2–3), 145.
4. (a) Sun, J.-H.; Teleha, C. A.; Yan, J.-S.; Rodgers, J. D.; Nugiel, D. A. Efficient
Synthesis of 5-(Bromomethyl)-and 5-(aminomethyl)-1-THP-indazloe. J. Org.
Chem. 1997, 62, 5627; (b) 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. Potent cyclic urea HIV protease inhibitors
with benzofused heterocycles as P2/P2’ groups. Bio. Med. Chem. Lett. 1996, 6,
2919.
5. Ikeda, Y.; Takano, N.; Matsushita, H.; Shiraki, Y.; Koide, T.; Nagashima, R.;
Fujimura, Y.; Shindo, M.; Suzuki, S.; Iwasaki, T. Pharmacological studies on a
new thymoleptic antidepressant, 1-[3-(dimethylamino)propyl]-5-methyl-3-phenyl-
1H-indazole (FS-32). Arzneim.-Forsch. 1979, 29, 511.
6. Corsi, G.; Palazzo, G.; Germani, C.; Barcellona, P. S.; Silvestrini, B. 1-Halobenzyl-
1H-indazole-3-carboxylic acid. A new class of antispermatogenic agents. J. Med.
Chem. 1976, 19, 778.
7. Song, J. J.; Yee, N. K. Synthesis of 1-aryl-1H-indazoles via the palladium-catalyzed
cyclization of N-aryl-N0-(o-bromobenzyl)hydrazines and [N-aryl-N0-(o-bromo-
benzyl)-hydrazinato-N0]-triphenylphosphonium bromides. Tetrahedron Lett. 2001,
42, 2937–2940.
8. Lebedev, A. Y.; Khartulyari, A. S.; Voskoboynikov, A. Z. Synthesis of 1-Aryl-1H-
indazoles via palladium-catalyzed intramolecular amination of aryl halides. J. Org.
Chem. 2005, 70, 596–602.
9. Klapars, A.; Antilla, J. C.; Huang, X.-H.; Buchwald, S. L. A general and efficient
copper catalyst for the amidation of aryl halides and the N-arylation of nitrogen
heterocycles. J. Am. Chem. Soc. 2001, 123, 7727–7729.