Application of the palladium-catalyzed N-arylation of hydrazones to deactivated heteroaryl halides in the synthesis of pyrazoles

Tetrahedron Letters

Volumn 45, Issue 30, 2004, Pages 5935-5937

  Haddad, Nizar ^a   Salvagno, Annette ^a   Busacca, Carl ^a  

^a BOEHRINGER INGELHEIM PHARMACEUTICALS INC   (United States)

Author keywords

Inactivated heteroaryl halides; Synthesis of heteroaryl pyrazoles

Indexed keywords

ACID; HALIDE; HYDRAZONE DERIVATIVE; PALLADIUM; PYRAZOLE;

ARTICLE; ARYLATION; CATALYSIS; CHEMICAL REACTION; CYCLIZATION; SYNTHESIS;

EID: 3242773632     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.05.038     Document Type: Article

References (10)

1. Regan J., Breitfelder S., Cirillo P., Gilmore T., Graham A.G., Hickey E., Klaus B., Madwed J., Moriak M., Moss N., Pargellis C., Pav S., Proto A., Swinamer A., Tong L., Torcellini C. J. Med. Chem. 45:2002;299
2. Regan J., Capolino A., Cirillo P.F., Gilmore T., Graham A.G., Hickey E., Kroe R.R., Madwed J., Moriak M., Nelson R., Pargellis C.A., Swinamer A., Torcellini C., Tsang M., Moss N. J. Med. Chem. 46:2003;4676
3. Sawyer J.S., Anderson B.D., Beight D.W., Campbell R.M., Jones M.L., Herron D.K., Lampe J.W., McCowan J.R., McMillen W.T., Mort N., Parsons S., Smith E.C.R., Vieth M., Weir L.C., Yan L., Zhang F., Yingling J.M. J. Med. Chem. 46:2003;3953
4. Haddad N., Baron J. Tetrahedron Lett. 43:2002;2171
5. Wolfe J.P., Tomori H., Sadighi J.P., Yin J., Buchwald S.L. J. Org. Chem. 65:2000;1158
6. For palladium catalyzed coupling of hydrazones see Wagaw S., Yang H.B., Buchwald S.L. J. Am. Chem. Soc. 120:1998;6621
7. Hartwig J.F. Angew. Chem., Int. Ed. 37:1998;2090
8. Arterburn J.B., Rao K.V., Ramdas R., Dible B.R. Org. Lett. 3:2001;1351
9. All new compounds were characterized by full spectroscopic data. Yields refer to chromatographed materials with purity of >95%
10. 4, concentrated under reduced pressure, the crude product was then purified by column chromatography.