Syntheses of Indoles via a Palladium-Catalyzed Annulation between lodoanilines and Ketones

Journal of Organic Chemistry

Volumn 62, Issue 9, 1997, Pages 2676-2677

  Chen, Cheng Yi ^a   Lieberman, David R ^a   Larsen, Robert D ^a   Verhoeven, Thomas R ^a   Reider, Paul J ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANILINE DERIVATIVE; INDOLE DERIVATIVE; KETONE DERIVATIVE; PALLADIUM;

ARTICLE; CATALYSIS; DRUG SYNTHESIS;

EID: 0030908560     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970278i     Document Type: Article

References (30)

1. (a) Saxton, J. E. Indoles;, Wiley-Interscience: New York, 1983; Part 4.
2. (b) Saxton, J. E. Nat. Prod. Rep. 1994, 493; 1995, 387.
3. (b) Saxton, J. E. Nat. Prod. Rep. 1994, 493; 1995, 387.
4. (c) Ihara, M.; Fukumoto, K. Nat. Prod. Rep. 1995, 277.
5. For reviews on the Fischer indole reaction, see: (a) Robinson, B. The Fischer Indole Synthesis; Wiley-Interscience: New York, 1982. (b) Hughes, D. L. Org. Prep. Proc. Int. 1993, 25, 607.
6. For reviews on the Fischer indole reaction, see: (a) Robinson, B. The Fischer Indole Synthesis; Wiley-Interscience: New York, 1982. (b) Hughes, D. L. Org. Prep. Proc. Int. 1993, 25, 607.
7. (c) Gribble, G. W. Contemp. Org. Synth. 1994, 1, 1 and references cited therein.
8. (a) Odle, R.; Blevins, B.; Ratcliff, M.; Hegedus, L. S. J. Org. Chem. 1980, 45, 2709.
9. (b) Kasahara, A.; Izumi, T.; Murakami, S.; Yanai, H.; Takatori, M. Bull. Chem. Soc. Jpn. 1986, 59, 927.
10. (c) Larock, R. C.; Babu, S. Tetrahedron Lett. 1987, 28, 5291.
11. (d) Larock, R. C.; Yum, E. K. J. Am. Chem. Soc. 1991, 113, 6689.
12. (e) Larock, R. C.; Zenner, J. M. J. Org. Chem. 1995, 60, 482.
13. (f) Desarbre, E.; Merour, J.-Y. Tetrahedron Lett. 1996, 37, 43 and references cited therein.
14. For examples of couplings with 1,3-dicarbonyl systems, see: (a) Iida, H.; Yuasa, Y.; Kibayashi, C. J. Org, Chem. 1980, 45, 2938-2942. (b) Sakamoto, T.; Nagano, T.; Kondo, Y.; Yamanake, H. Synthesis 1990, 215. (c) Koerber-Ple, K.; Massiot G. Synlett 1994, 759.
15. For examples of couplings with 1,3-dicarbonyl systems, see: (a) Iida, H.; Yuasa, Y.; Kibayashi, C. J. Org, Chem. 1980, 45, 2938-2942. (b) Sakamoto, T.; Nagano, T.; Kondo, Y.; Yamanake, H. Synthesis 1990, 215. (c) Koerber-Ple, K.; Massiot G. Synlett 1994, 759.
16. For examples of couplings with 1,3-dicarbonyl systems, see: (a) Iida, H.; Yuasa, Y.; Kibayashi, C. J. Org, Chem. 1980, 45, 2938-2942. (b) Sakamoto, T.; Nagano, T.; Kondo, Y.; Yamanake, H. Synthesis 1990, 215. (c) Koerber-Ple, K.; Massiot G. Synlett 1994, 759.
17. For reviews of the Heck reaction, see: (a) Heck, R. F. Org. React. 1982, 27, 345, (b) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. (c) Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2.
18. For reviews of the Heck reaction, see: (a) Heck, R. F. Org. React. 1982, 27, 345, (b) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. (c) Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2.
19. For reviews of the Heck reaction, see: (a) Heck, R. F. Org. React. 1982, 27, 345, (b) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. (c) Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2.
20. 1D agonist, rizatriptan: (a) Chen, C.; Lieberman, D. R.; Larsen, R. D.; Reamer, R. A.; Verhoeven, T. R.; Reider, P. J.; Cottrell, I. F.; Houghton, P. G. Tetrahedron Lett. 1994, 35, 6981. (b) Street, L. J.; Baker, R.; Davey, W. B.; Guiblin, A. R.; Jelley, R.; Reeve, A. J.; Routledge, H.; Sternfeld, F.; Watt, A. P.; Beer, M. S.; Middlemiss, D. N.; Noble, A. J.; Stanton, J. A.; Scholey, K.; Hargreaves, R. J.; Sohal, B.; Graham, M. I.; Matassa, V. G. J. Med. Chem. 1995, 38, 1799.
21. 1D agonist, rizatriptan: (a) Chen, C.; Lieberman, D. R.; Larsen, R. D.; Reamer, R. A.; Verhoeven, T. R.; Reider, P. J.; Cottrell, I. F.; Houghton, P. G. Tetrahedron Lett. 1994, 35, 6981. (b) Street, L. J.; Baker, R.; Davey, W. B.; Guiblin, A. R.; Jelley, R.; Reeve, A. J.; Routledge, H.; Sternfeld, F.; Watt, A. P.; Beer, M. S.; Middlemiss, D. N.; Noble, A. J.; Stanton, J. A.; Scholey, K.; Hargreaves, R. J.; Sohal, B.; Graham, M. I.; Matassa, V. G. J. Med. Chem. 1995, 38, 1799.
22. 2, see: (a) McCrindle, R.; Ferguson, G.; Arsenault, G. J.; McAlees, A. J.; Stephenson, D. K. J. Chem. Res. Synop. 1984, 360. (b) Guram, A. S.; Rennels, R. A.; Buchwald, S. L. Angew. Chem., Int. Ed. Engl. 1995, 34, 1348. (c) Clark, F. R. S.; Norman, R. O. C.; Thomas, C. B. J. Chem. Soc., Perkin Trans. 1 1975, 121.
23. 2, see: (a) McCrindle, R.; Ferguson, G.; Arsenault, G. J.; McAlees, A. J.; Stephenson, D. K. J. Chem. Res. Synop. 1984, 360. (b) Guram, A. S.; Rennels, R. A.; Buchwald, S. L. Angew. Chem., Int. Ed. Engl. 1995, 34, 1348. (c) Clark, F. R. S.; Norman, R. O. C.; Thomas, C. B. J. Chem. Soc., Perkin Trans. 1 1975, 121.
24. 2, see: (a) McCrindle, R.; Ferguson, G.; Arsenault, G. J.; McAlees, A. J.; Stephenson, D. K. J. Chem. Res. Synop. 1984, 360. (b) Guram, A. S.; Rennels, R. A.; Buchwald, S. L. Angew. Chem., Int. Ed. Engl. 1995, 34, 1348. (c) Clark, F. R. S.; Norman, R. O. C.; Thomas, C. B. J. Chem. Soc., Perkin Trans. 1 1975, 121.
25. For a review of Bredt's rule, see: Shea, K. J. Tetrahedron 1980, 36, 1683.
26. 2 (112 mg, 0.5 mmol, 5 mol %) in dry DMF (30 mL) was degassed via vacuum/nitrogen purges and heated to 105°C. The mixture was heated at 105°C for 3 h or until the reaction was complete (usually <12 h). The reaction mixture was cooled to room temperature and partitioned between isopropyl acetate (150 mL) and water (50 mL). The organic layer was separated, washed with brine (50 mL), and concentrated under vacuum to dryness. The residue was chromatographed and crystallized from isopropyl acetate-heptane to give 1.32 g of tetrahydrocarbazole 4 (77%) as an off-white solid: mp 119-120°C (lit. mp 118-120°C: Rogers, C. U.; Corson, B. B Organic Synthesis; Wiley: New York, 1967; Collect. Vol. IV, p 884). The ketone charge ranged from 1 to 3 equiv.
27. 2 (112 mg, 0.5 mmol, 5 mol %) in dry DMF (30 mL) was degassed via vacuum/nitrogen purges and heated to 105°C. The mixture was heated at 105°C for 3 h or until the reaction was complete (usually <12 h). The reaction mixture was cooled to room temperature and partitioned between isopropyl acetate (150 mL) and water (50 mL). The organic layer was separated, washed with brine (50 mL), and concentrated under vacuum to dryness. The residue was chromatographed and crystallized from isopropyl acetate-heptane to give 1.32 g of tetrahydrocarbazole 4 (77%) as an off-white solid: mp 119-120°C (lit. mp 118-120°C: Rogers, C. U.; Corson, B. B Organic Synthesis; Wiley: New York, 1967; Collect. Vol. IV, p 884). The ketone charge ranged from 1 to 3 equiv.
28. 3 in methanol following the procedure in ref 6 in 86% and 92% yield, respectively.
29. 4a failed with cyclopentanedione.
30. Jones, G. B.; Chapman, B. J. J. Org. Chem. 1993, 58, 5558.