Synthesis of 3-indazolecarboxylic esters and amides via Pd-catalyzed carbonylation of 3-iodoindazoles

Synthesis

Volumn , Issue 19, 2011, Pages 3089-3098

  Buchstaller, Hans Peter ^a   Wilkinson, Kai ^a   Burek, Kasimir ^b   Nisar, Yasmin ^b  

^a Merck Serono GmbH   (Germany)

^b MERCK KGAA   (Germany)

Author keywords

alkoxycarbonylation; amides; aminocarbonylation; carbonylation; esters; iodoindazole; palladium catalysis

Indexed keywords

ACID ESTER; ALKOXYCARBONYLATION; AMINOCARBONYLATION; CARBONYLATIONS; DIVERSE RANGE; FUNCTIONALIZED; GOOD YIELD; IODOINDAZOLE; PALLADIUM CATALYSIS; SYNTHETIC TRANSFORMATIONS; TITLE COMPOUNDS;

AMIDES; CARBOXYLIC ACIDS; CATALYSIS; ESTERIFICATION; ESTERS; FUNCTIONAL GROUPS; METHANOL; SYNTHESIS (CHEMICAL);

CARBONYLATION;

1H INDAZOLE 3 CARBOXYLIC ESTER DERIVATIVE; 3 INDAZOLECARBOXYLIC AMIDE; 3 INDAZOLECARBOXYLIC ESTER DERIVATIVE; 3 IODOINDAZOLE DERIVATIVE; 5 BROMO N BUTYL N METHYL 1H INDAZOLE 3 CARBOXAMIDE; AMIDE; ESTER DERIVATIVE; INDAZOLE DERIVATIVE; METHANOL; METHYL 1H INDAZOLE 3 CARBOXYLATE; METHYL 3 METHYL 1H INDAZOLE 3,5 DICARBOXYLATE; METHYL 4 METHYL 1H INDAZOLE 3 CARBOXYLATE; METHYL 5 BROMO 1H INDAZOLE 3 CARBOXYLATE; METHYL 5 FLUORO 1H INDAZOLE 3 CARBOXYLATE; METHYL 5 METHOXY 1H INDAZOLE 3 CARBOXYLATE; METHYL 5 NITRO 1H INDAZOLE 3 CARBOXYLATE; METHYL 6 CHLORO 1H INDAZOLE 3 CARBOXYLATE; METHYL 6 CYANO 1H INDAZOLE 3 CARBOXYLATE; METHYL 6 METHOXY 1H INDAZOLE 3 CARBOXYLATE; METHYL 6 METHYL 1H INDAZOLE 3 CARBOXYLATE; METHYL 6 NITRO 1H INDAZOLE 3 CARBOXYLATE; METHYL 7 METHYL 1H INDAZOLE 3 CARBOXYLATE; N BUTYL 5 FLUORO N METHYL 1H INDAZOLE 3 CARBOXAMIDE; N BUTYL 5 METHOXY N METHYL 1H INDAZOLE 3 CARBOXAMIDE; N BUTYL 6 CHLORO N METHYL 1H INDAZOLE 3 CARBOXAMIDE; N BUTYL N METHYL 1H INDAZOLE 3 CARBOXAMIDE; N BUTYL N,4 DIMETHYL 1H INDAZOLE 3 CARBOXAMIDE; N BUTYL N,7 DIMETHYL 1H INDAZOLE 3 CARBOXAMIDE; PALLADIUM; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; CARBONYLATION; CATALYSIS; CHEMICAL MODIFICATION; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 80053053442     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1260199     Document Type: Article

References (26)

1. Schmidt A, Beutler A, Snovydovych B, Eur. J. Org. Chem. 2008 4073
2. Cerecetto H, Gerpe A, Gonzlez M, Arn V J., OchoadeOcriz C, Mini-Rev. Med. Chem. 2005 5 869
3. Wynne G M., Wren S P., Van Well R M., Chancellor D R., Schroeer F, PCT Int. Appl. WO 2009/121623 2009; Chem. Abstr. 2009, 151, 425741
4. Aletru M, Damour D, Monseau C, Mougenot P, Namane C, Nardi F, Nemecek P, Philippo C, PCT Int. Appl. WO 2009/010660 2009; Chem. Abstr. 2009, 150, 168344
5. Wagner H, Langkopf E, Eckhardt M, Streicher R, Schoelch C, Schuler-Metz A, Pautsch A, PCT Int. Appl. WO 2009/016119 2009; Chem. Abstr. 2009, 150, 168522
6. Buchler I P., Hayes M J., Hedge S G., Hockerman S L., Jones D E., Kortum S W., Rico J G., Tenbrink R E., Wu K K., PCT Int. Appl. WO 2009/106982 2009; Chem. Abstr. 2009, 151, 313542, Buchler I P., Hayes M J., Hedge S G., Hockerman S L., Jones D E., Kortum S W., Rico J G., Tenbrink R E., Wu K K., PCT Int. Appl. WO 2009/106980 2009; Chem. Abstr. 2009, 151, 313541, Alisi M A., Cazzolla N, Furlotti G, Guglielmotti A, Polenzani L, PCT Int. Appl. WO 2009/062883 2009; Chem. Abstr. 2009, 150, 539708
7. Harada H, Morie T, Hirokawa Y, Terauchi H, Fujiwara I, Yoshida N, Kato S, Chem. Pharm. Bull. 1995 43 1912
8. Elliott E L., Bushell S M., Cavero M, Tolan B, Kelly T R., Org. Lett. 2005 7 2449
9. Yoshida T, Matsuura N, Yamamoto K, Doi M, Shimada K, Morie T, Kato S, Heterocycles 1996 43 2701
10. Buchheit K.-H, Gamse R, Giger R, Hoyer D, Klein F, Klöppner E, Pfannkuche H.-J, Mattes H, J. Med. Chem. 1995 38 2331
11. Collot V, Dallemagne P, Bovy R P., Rault S, Tetrahedron 1999 55 6917
12. Crestey F, Collot V, Stiebing S, Rault S, Synthesis 2006 3506
13. Grigg R, Mutton S P., Tetrahedron 2010 66 5515
14. Brennfhrer A, Neumann H, Beller M, Angew. Chem. Int. Ed. 2009 48 4114
15. Barnard C F. J., Organometallics 2008 27 5402
16. Tsuji J, Palladium Reagents and Catalysts: New Perspectives for the 21st Century Wiley Chichester (UK) 2004
17. Kumar K, Zapf A, Michalik D, Tillack A, Heinrich T, Böttcher H, Arlt M, Beller M, Org. Lett. 2004 6 7
18. Bartsch R A., Yang I.-W J., Heterocycl. Chem. 1984 21 1063
19. Lukin K, Hsu M C., Fernando D, Leanna M R., J. Org. Chem. 2006 71 8166
20. Batt D G., Petraitis J J., Houghten G C., Modi D P., Cain G A., Corjay M H., Mousa S A., Bouchard P J., Forsythe M S., Harlow P P., Barbera F A., Spitz S M., Wexler R R., Jadhav P K., J. Med Chem. 2000 43 41
21. Yager K, Chu S, Appelt K, Li X, U.S. Pat. Appl. Publ. US2005/54697 2005; Chem. Abstr. 2005, 142, 316830
22. Arrington K L., Fraley M E., Garbaccio R M., Huang S Y., Lindsley C W., Steen J T., Yang F, PCT Int. Appl. WO 2006/086255 2006; Chem. Abstr. 2006, 145: 249199
23. Wrzeciono U, Nieweglowska W, Szot M, Pharmazie 1979 34 399
24. Georg G I., Tash J S., Chakrasali R, Jakkaraj S R., U.S. Pat. Appl. Publ. US2006/47126 2006; Chem. Abstr. 2006, 144, 274268
25. Schmidt A, Snovydovych B, Habeck T, Droettboom P, Gjikaj M, Adam A, Eur. J. Org. Chem. 2007 4909
26. Piozzi F, Ronchi A U., Gazz. Chim. Ital. 1963 93 3