Highly efficient synthesis of 5-benzyl-3-aminoindazoles

Tetrahedron Letters

Volumn 50, Issue 25, 2009, Pages 3098-3100

  Orsini, Paolo ^a   Menichincheri, Maria ^a   Vanotti, Ermes ^a   Panzeri, Achille ^a  

^a NERVIANO MEDICAL SCIENCES   (Italy)

Author keywords

3 Aminoindazoles; Diarylcarbinols; Diarylmethanes; Suzuki Miyaura reaction

Indexed keywords

5 BENZYL 3 AMINOINDAZOLE; ALKANE DERIVATIVE; INDAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 65449156358     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.04.024     Document Type: Article

References (36)

1. Cerecetto H., Gerpe A., González M., Arán V.J., and Ochoa de Ocáriz C. Mini-Rev. Med. Chem. 5 (2005) 869-878
2. Schmidt A., Beutler A., and Snovydovych B. Eur. J. Org. Chem. 24 (2008) 4073-4095
3. Stocks M.J., Barber S., Ford R., Leroux F., St-Galley S., Teague S., and Xue Y. Bioorg. Med. Chem. Lett. 15 (2005) 3459-3462
4. Dai Y., Hartandi K., Ji Z., Ahmed A.A., Albert D.H., Bauch J.L., Bouska J.J., Bousquet P.F., Cunha G.A., Glaser K.B., Harris C.M., Hickman D., Guo J., Li J., Marcotte P.A., Marsh K.C., Moskey M.D., Martin R.L., Olson A.M., Osterling D.J., Pease L.J., Soni N.B., Stewart K.D., Stoll V.S., Tapang P., Reuter D.R., Michaelides M.R., and Davidsen S.K. J. Med. Chem. 50 (2007) 1584-1597
5. Lee J., Choi H., Kim K.-H., Jeong S., Park J.-W., Baek C.-S., and Lee S.-H. Bioorg. Med. Chem. Lett. 18 (2008) 2292-2295
6. Vasudevan A., Souers A.J., Freeman J.C., Verzal M.K., Gao J., Mulhern M.M., Wodka D., Lynch J.K., Engstrom K.M., Wagaw S.H., Brodjian S., Dayton B., Falls D.H., Bush E., Brune M., Shapiro R.D., Marsh K.C., Hernandez L.E., Collins C.A., and Kym P.R. Bioorg. Med. Chem. Lett. 15 (2005) 5293-5297
7. Steffan R.J., Matelan E., Ashwell M.A., Moore W.J., Solvibile W.R., Trybulski E., Chadwick C.C., Chippari S., Kenney T., Eckert A., Borges-Marcucci L., Keith J.C., Xu Z., Mosyak L., and Harnish D.C. J. Med. Chem. 47 (2004) 6435-6438
8. Lombardi Borgia, A.; Menichincheri, M.; Orsini, P.; Panzeri, A.; Perrone, E.; Vanotti, E.; Nesi, M.; Marchionni, C. WO 2009/013126, 2009.
9. Antonysamy S., Hirst G., Park F., Sprengeler P., Stappenbech F., Steensma R., Wilson M., and Wong M. Bioorg. Med. Chem. Lett. 19 (2009) 279-282
10. Dai Y., Hartandi K., Ji Z., Ahmed A.A., Albert H.D., Bauch L.J., Bouska J.J., Bousquet F.P., Cunha A.G., Glaser B.K., Harris M.C., Hickman D., Guo J., Li J., Marcotte A.P., Marsh C.K., Moskey D.M., Martin L.R., Olson M.A., Osterling J.D., Pease J.L., Soni B.N., Stewart D.K., Stoll S.V., Tapang P., Reuter R.D., Davidsen K.S., and Michaelides R.M. J. Med. Chem. 50 (2007) 1584-1597
11. Woods W.K., Fischer P.J., Claiborne A., Li T., Thomas A.S., Zhu G.-D., Diebold B.R., Liu X., Shi Y., Klinghofer V., Han K.E., Guan R., Magnone R.S., Johnson F.E., Bouska J.J., Olson M.A., de Jong R., Oltersdorf T., Luo Y., Rosenberg H.S., Giranda L.V., and Li Q. Bioorg. Med. Chem. 14 (2006) 6832-6846
12. Cui J.J., Araldi G.-L., Reiner E.J., Reddy M.K., Kemp J.S., Ho Z.J., Siev V.D., Mamedova L., Gibson S.T., Gaudette A.J., Minami K.N., Anderson M.S., Bradbury E.A., Nolan G.T., and Semple E.J. Bioorg. Med. Chem. Lett. 12 (2002) 2925-2930
13. Nichele T.Z., and Monteiro A.L. Tetrahedron Lett. 48 (2007) 7472-7475
14. Yoshida H., Watanabe M., Morishita T., Ohshita J., and Kunai A. Chem. Commun. (2007) 1505-1507
15. Chupak L.S., Wolkowski J.P., and Chantigny Y.A. J. Org. Chem. 74 (2009) 1388-1390
16. Sun H.-B., Li B., Chen S., Li J., and Hua R. Tetrahedron 63 (2007) 10185-10188
17. Dong Z., Manolikakes G., Li J., and Knochel P. Synthesis (2009) 681-686
18. Kuwano R., and Yokogi M. Org. Lett. 7 (2005) 945-947
19. McLaughlin M. Org. Lett. 7 (2005) 4875-4878
20. Kuwano R. Synthesis 7 (2009) 1049-1061
21. Wai J.S., Egbertson M.S., Payne L.S., Fisher T.E., Embrey M.W., Tran L.O., Melamed J.Y., Langford H.M., Guare J.P., Zhuang L., Gray V.E., Vacca J.P., Holloway M.K., Naylor-Olsen A.M., Hazuda D.J., Felock P.J., Wolfe A.L., Stillmock K.A., Schleif W.A., Gabryelski L.J., and Young S.D. J. Med. Chem. 43 (2000) 4923-4926
22. 4Cl. EtOAc was added, the layers were separated, and the aqueous phase was extracted twice with EtOAc. Organic layers were collected, washed with brine, dried, and evaporated. Trituration with i-propyl ether/n-hexane 1:1 afforded the title products in yields of 85-90%.
23. Gemma S., Campiani G., Butini S., Kukreja G., Joshi B.P., Persico M., Catalanotti B., Novellino E., Fattorusso E., Nacci V., Savini L., Taramelli D., Basilico N., Morace G., Yardley V., and Fattorusso C. J. Med. Chem. 50 (2007) 595-598
24. General procedure for the preparation of diarylmethanes 2a-b: Diarylcarbinols (1 equiv) and sodium iodide (10 equiv) were stirred in acetonitrile (4 mL/mmol carbinol) under nitrogen at 60 °C in oil bath. To the reaction mixture TMSCl (10 equiv) was gradually added over a period of 8 h. The mixture was diluted with EtOAc and washed with water, saturated aqueous sodium bicarbonate, 10% aqueous sodium thiosulfate, and brine. Trituration with ethyl ether afforded the title products in yields of 85-95%.
25. Cain G.A., and Holler E.R. Chem. Commun. (2001) 1168-1169
26. Langle S., Abarbri M., and Duchêne A. Tetrahedron Lett. 44 (2003) 9255-9258
27. Nobre S.M., and Monteiro A.L. Tetrahedron Lett. 45 (2004) 8225-8228
28. Fairlamb S.J.I., Sehnal P., and Taylor J.K.R. Synthesis 3 (2009) 508-510
29. Ines B., Moreno I., SanMartin R., and Dominguez E. J. Org. Chem. 73 (2008) 8448-8451
30. Molander A.G., and Elia D.M. J. Org. Chem. 71 (2006) 9198-9202
31. Chalen L., Doucet H., and Santelli M. Synlett (2003) 1668-1672
32. Chowdhury S., and Georghiou E.P. Tetrahedron Lett. 40 (1999) 7599-7603
33. 3P: aryl iodide > benzyl bromide > benzyl chloride > aryl bromide.
34. From Small Molecules, Inc.
35. 4 and evaporated to dryness. The residue was then purified by flash chromatography (n-hexane/EtOAc) to provide the desired diarylmethane in yields of 60-90%.
36. 2/EtOH) to provide the desired 3-aminoindazole in yields of 75-90%.