Regioselective rapid analogue syntheses of 1-methyl-3,5-diarylpyrazoles via palladium-catalysed coupling to 3(5)-pyrazolyl nonaflates

Synlett

Volumn , Issue 5, 2004, Pages 795-798

  Bourrain, Sylvie ^a   Ridgill, Mark ^a   Collins, Ian ^a,b  

^a NEUROSCIENCE RESEARCH CENTRE   (United Kingdom)

^b INSTITUTE OF CANCER RESEARCH   (United Kingdom)

Author keywords

Chemoselectivity; Cross coupling; Heterocycles; Palladium; Regioselectivity

Indexed keywords

3(5) PYRAZOLYLNONAFLATE; BROMIDE; PALLADIUM; PYRAZOLE DERIVATIVE; REAGENT; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ARTICLE; CATALYSIS; CHEMICAL PROCEDURES; CHEMICAL STRUCTURE; HYDROLYSIS; SUZUKI REACTION; SYNTHESIS;

EID: 1942521608     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-820020     Document Type: Article

References (28)

1. For reviews of the synthesis and biological activity of N-alkyl pyrazoles see: (a) Elguero, J. Comprehensive Heterocyclic Chemistry, Vol. 5; Potts, K. T., Ed.; Pergamon: Oxford, 1984, 167. (b) Elguero, J. Comprehensive Heterocyclic Chemistry II, Vol. 3; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.; Pergamon: Oxford, 1996, 1.
2. For reviews of the synthesis and biological activity of N-alkyl pyrazoles see: (a) Elguero, J. Comprehensive Heterocyclic Chemistry, Vol. 5; Potts, K. T., Ed.; Pergamon: Oxford, 1984, 167. (b) Elguero, J. Comprehensive Heterocyclic Chemistry II, Vol. 3; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.; Pergamon: Oxford, 1996, 1.
3. For examples of Pd-catalysed cross-coupling to N-alkyl-or N-benzyl-3(5)-halopyrazoles see: (a) Tretyakov, E. V.; Knight, D. W.; Vasilevsky, S. F. J. Chem. Soc., Perkin Trans. 1 1999, 3713. (b) Paulson, A. S.; Eskildsen, J.; Vedso, P.; Begtrup, M. J. Org. Chem. 2002, 67, 3904. (c) Cottineau, B.; Chenault, J. Synlett 2002, 769. (d) Balle, T.; Andersen, K.; Vedso, P. Synthesis 2002, 1509. (e) Eskildsen, J.; Ostergaard, N.; Vedso, P.; Begtrup, M. Tetrahedron 2002, 58, 7635.
4. For examples of Pd-catalysed cross-coupling to N-alkyl-or N-benzyl-3(5)-halopyrazoles see: (a) Tretyakov, E. V.; Knight, D. W.; Vasilevsky, S. F. J. Chem. Soc., Perkin Trans. 1 1999, 3713. (b) Paulson, A. S.; Eskildsen, J.; Vedso, P.; Begtrup, M. J. Org. Chem. 2002, 67, 3904. (c) Cottineau, B.; Chenault, J. Synlett 2002, 769. (d) Balle, T.; Andersen, K.; Vedso, P. Synthesis 2002, 1509. (e) Eskildsen, J.; Ostergaard, N.; Vedso, P.; Begtrup, M. Tetrahedron 2002, 58, 7635.
5. For examples of Pd-catalysed cross-coupling to N-alkyl-or N-benzyl-3(5)-halopyrazoles see: (a) Tretyakov, E. V.; Knight, D. W.; Vasilevsky, S. F. J. Chem. Soc., Perkin Trans. 1 1999, 3713. (b) Paulson, A. S.; Eskildsen, J.; Vedso, P.; Begtrup, M. J. Org. Chem. 2002, 67, 3904. (c) Cottineau, B.; Chenault, J. Synlett 2002, 769. (d) Balle, T.; Andersen, K.; Vedso, P. Synthesis 2002, 1509. (e) Eskildsen, J.; Ostergaard, N.; Vedso, P.; Begtrup, M. Tetrahedron 2002, 58, 7635.
6. For examples of Pd-catalysed cross-coupling to N-alkyl-or N-benzyl-3(5)-halopyrazoles see: (a) Tretyakov, E. V.; Knight, D. W.; Vasilevsky, S. F. J. Chem. Soc., Perkin Trans. 1 1999, 3713. (b) Paulson, A. S.; Eskildsen, J.; Vedso, P.; Begtrup, M. J. Org. Chem. 2002, 67, 3904. (c) Cottineau, B.; Chenault, J. Synlett 2002, 769. (d) Balle, T.; Andersen, K.; Vedso, P. Synthesis 2002, 1509. (e) Eskildsen, J.; Ostergaard, N.; Vedso, P.; Begtrup, M. Tetrahedron 2002, 58, 7635.
7. For examples of Pd-catalysed cross-coupling to N-alkyl-or N-benzyl-3(5)-halopyrazoles see: (a) Tretyakov, E. V.; Knight, D. W.; Vasilevsky, S. F. J. Chem. Soc., Perkin Trans. 1 1999, 3713. (b) Paulson, A. S.; Eskildsen, J.; Vedso, P.; Begtrup, M. J. Org. Chem. 2002, 67, 3904. (c) Cottineau, B.; Chenault, J. Synlett 2002, 769. (d) Balle, T.; Andersen, K.; Vedso, P. Synthesis 2002, 1509. (e) Eskildsen, J.; Ostergaard, N.; Vedso, P.; Begtrup, M. Tetrahedron 2002, 58, 7635.
8. For examples of Pd-catalysed cross-coupling to N-aryl-3(5)-halopyrazoles see: (a) Wang, X.-J.; Tan, J.; Grozinger, K. Tetrahedron Lett. 2000, 41, 4713. (b) Organ, M. G.; Mayer, S. J. Comb. Chem. 2003, 5, 118.
9. (4) For examples of Pd-catalysed cross-coupling to N-aryl-3(5)- halopyrazoles see: (a) Wang, X.-J.; Tan, J.; Grozinger, K. Tetrahedron Lett. 2000, 41, 4713. (b) Organ, M. G.; Mayer, S. J. Comb. Chem. 2003, 5, 118.
10. Regan, J.; Breitfelder, S.; Crillo, 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. 2002, 45, 2994.
11. For a review see: Varvounis, G.; Fiamegos, Y.; Pilidis, G. Adv. Het. Chem. 2001, 80, 73.
12. (a) Hamper, B. C.; Kurtzweil, M. L.; Beck, P. J. Org. Chem. 1992, 57, 5680.
13. (b) Sucrow, W.; Slopianka, M.; Vetter, H. J. Chem. Ber. 1978, 111, 791.
14. Hendrickson, J. B.; Hussoin, M. S. Synthesis 1989, 217.
15. Morris, J.; Wishka, D. G. Synthesis 1994, 43.
16. Rottlander, M.; Knochel, P. J. Org. Chem. 1998, 63, 203.
17. Renold, P.; Madero, E.; Maetke, T. J. Chromatogr., A 2001, 908, 143.
18. (a) Collins, I. J. Chem. Soc., Perkin Trans. 1 2000, 2845.
19. (b) Collins, I. J. Chem. Soc., Perkin Trans. 1 2002, 1921.
20. Boschi, P. M.; Gozzo, A. L. US Pat. Appl. 4256902, 1981; Chem. Abstr. 1981, 95, 7281.
21. Boschi, P. M.; Gozzo, A. L. US Pat. Appl. 4256902, 1981; Chem. Abstr. 1981, 95, 7281.
22. (a) Rappe, C. Arkiv Kemi 1964, 21, 503.
23. (b) Kim, H.; Hoffman, H. M. R. Eur. J. Org. Chem. 2000, 2195.
24. Rappe, C.; Andersson, K. Arkiv Kemi 1965, 24, 303.
25. Coates, R. M.; Stack, D. P. Synthesis 1984, 434.
26. (a) Prepared by a modification of the method described by: Zinner, G.; Gebhardt, U. Arch. Pharm. 1971, 304, 706.
27. 2 (3:97 then 5:95) gave ethyl 2-methyl- hydrazinecarboxylate (13.5 g, 85% pure by NMR) then ethyl 3-methylhydrazine- carboxylate (21.3 g, 93% pure by NMR).
28. Bishop, B. C.; Brands, K. M. J.; Gibb, A. D.; Kennedy, D. J. Synthesis 2004, 43.