A tandem heck-carbocyclization/suzuki-coupling approach to the stereoselective syntheses of asymmetric 3,3-(diarylmethylene)indolinones

Journal of Organic Chemistry

Volumn 70, Issue 9, 2005, Pages 3741-3744

  Cheung, Wing S ^a   Patch, Raymond J ^a   Player, Mark R ^a  

^a Johnson Johnson Pharmaceutical R D   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; ORGANIC SOLVENTS; PALLADIUM; REACTION KINETICS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

CHEMICAL EQUATIONS; COORDINATING LIGANDS; STEREOSELECTIVE SYNTHESIS; SUZUKI-COUPLINGS;

AROMATIC HYDROCARBONS;

3,3 (DIARYLMETHYLENE) INDOLINONE; INDOLE DERIVATIVE; KETONE DERIVATIVE; PALLADIUM; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; CARBOCYCLIZATION; CATALYSIS; CATALYST; CYCLIZATION; HECK REACTION; STEREOCHEMISTRY; SUZUKI REACTION;

EID: 17744380007     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050016d     Document Type: Article

References (20)

1. (a) Sun, L.; Liang, C.; Shirazian, S.; Zhou, Y.; Miller, T.; Cui, J.; Fukuda, J. Y.; Chu, J. Y.; Nematalla, A.; Wang, X.; Chen, H.; Sistla, A.; Luu, T. C.; Tang, F.; Wei, J.; Tang, C. J. Med. Chem. 2003, 46, 1116-9.
2. (b) Sun, L.; Tran, N.; Liang, C.; Hubbard, S.; Tang, F.; Lipson, K.; Schreck, R.; Zhou, Y.; McMahon, G.; Tang, C. J. Med. Chem. 2000, 43, 2655-63.
3. Mendel, D. B.; Laird, A. D.; Xin, X.; Louie, S. G.; Christensen, J. G.; Li, G.; Schreck, R. E.; Abrams, T. J.; Ngai, T. J.; Lee, L. B.; Murray, L. J.; Carver, J.; Chan, E.; Moss, K. G.; Haznedar, J. O.; Sukbuntherng, J.; Blake, R. A.; Sun, L.; Tang, C.; Miller, T.; Shirazian, S.; McMahon, G.; Cherrington, J. M. Clin. Cancer Res. 2003, 9, 327-37.
4. (a) Eberwein, D. J.; Harrington, L.; Griffin, R.; Tadepalli, S.; Knick, V.; Phillips, K.; Dickerson, S.; Davis, S. Proc. Am. Assoc. Cancer Res. 2002, 43: Abst 1611.
5. (b) Davis, S. T.; Dickerson, S. H.; Harris, P. A.; Hunter, R. N.; Kuyper, L. F.; Luzzio, M. J.; Veal, J. M.; Walker, D. H. US Pat. 6,387,919, 2002.
6. Hauf, S.; Cole, R. W.; LaTerra, S.; Zimmer, C.; Schnapp, G.; Walter, R.; Heckel, A.; van Meel, J.; Rieder, C. L.; Peters, J. M. J. Cell Biol. 2003, 161, 281-94.
7. Sato, A.; Asao, T.; Hagiwara, Y.; Kitade, M.; Yamazaki, Y. US Pat. 5,965,600, 1999.
8. While this paper was in preparation, Yanada et al. published a complementary method for the syntheses of 3-diarylmethylidenylox-indoles involving tandem indium carbometalation and palladium-catalyzed coupling reactions. The applicability of their method with N-containing heterocycles was not presented. Yanada, R.; Obika, M.; Takemoto, Y. Org. Lett. 2004, 6, 2825-2828.
9. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
10. 4 (0.083 g, 0.393 mmol), and phenylboronic acid (0.029 g, 0.236 mmol). The sealed reaction mixture was irradiated in a microwave synthesizer (Smith Synthesizer, Personal Chemistry) at 100°C for 30 min. The reaction mixture was concentrated under reduced pressure, and the resulting crude product was purified by silica gel chromatography [hexanes/EtOAc (4:1)] to afford 9 (78%) as yellow oil.
11. The structure of this product was confirmed by comparison with the authentic diphenylmethylidene indolinone, prepared from the condensation of 5-chlorooxindole and benzophenone with sodium hydroxide in refluxing toluene.
12. Li, G. Y. J. Org. Chem. 2002, 67, 3643.
13. Andrus, M. B.; Song, C. Org. Lett. 2001, 3, 3761.
14. Wolf, J. P.; Singer, R. A.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 9550.
15. Savarin, C.; Liebeskind, L. S. Org. Lett. 2001, 1, 2149.
16. Phosphine ligands investigated included the monodentate ligands: (2-dicycohexyphosphino)biphenyl, (2-di-tert-butylphosphino)-biphenyl, and 2,8,9-triobutyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]-undecane, as well as bidentate ligands: 2-di-tert-butylphosphino-2′-(N,N-dimethylamino)- biphenyl, 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (XANTPHOS), and 1,1′-bis(diphenylphosphino)-ferrocene (dppf).
17. 3 (0.05 equiv), phosphine ligand (0.1-0.2 equiv), copper 2-thiophenecarboxylate CuTC (1.4 equiv), and of 2-chloropyridine-5- boronic acid (1.4 equiv) in THF at ambient temperature for 15 h.
18. 2, dichlorobis-(benzonitrile)palladium(II), and dichloro(acetonitrile)palladium(II) .
19. The general procedure involved stirring palladium catalyst (0.1 equiv), CuTC (1.4 equiv), 2-choropyridine-5-boronic acid (1.4 equiv), and 8 (1 equiv) in anhydrous THF at room temperature for 10 h.
20. Lesser concentrations of MeOH or DMF resulted in incomplete reactions. In contrast, excess MeOH or DMF was detrimental to the regioselectivity of this process.