Solid-phase synthesis of indoles using the palladium-catalysed coupling of alkynes with iodoaniline derivatives

Tetrahedron Letters

Volumn 38, Issue 13, 1997, Pages 2307-2310

  Fagnola, Maria Chiara ^a   Candiani, Ilaria ^a   Visentin, Giuseppina ^a   Cabri, Walter ^a,b   Zarini, Franco ^a   Mongelli, Nicola ^a   Bedeschi, Angelo ^a  

^a PFIZER INC   (United States)

^b BRISTOL MYERS SQUIBB   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE DERIVATIVE;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS;

EID: 0031592570     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00300-6     Document Type: Article

References (21)

1. 2. For a recent review on small molecules libraries, see for instance Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555.
2. 3. Desphande, M. S. Tetrahedron Letters 1994, 35, 5613. Kuo-Long, Y.; Desphande, M. S.; Dolatrai, M. V. Tetrahedron Letters 1994, 35, 8919. Frenette, R.; Friesen, R. W. Tetrahedron Letters 1994, 35, 9177. Forman, F. W.; Sucholeiki, I. J. Org. Chem. 1995, 60, 523. Plunkett, M. J. J. Am. Chem. Soc. 1995, 117, 3306. Hiroshige, M.; Hauske, J. R.; Zhou, P. J. Am. Chem. Soc. 1995, 777, 11590. Hiroshige, M.; Hauske, J. R.; Zhou, P. Tetrahedron Letters 1995, 36, 4567. Goff, D. A.; Zukermann, R. N. J. Org. Chem. 1995, 60, 5748. Marquais, S.; Arlt, M. Tetrahedron Letters 1996, 37, 5491. Sung Koh, J.; Ellman, J. A. J. Org. Chem. 1996, 61, 4494. Guiles, J. W.; Johnson, S. G.; Murray, W. V. J. Org. Chem. 1996, 61, 5169. Brown, D. S.; Armstrong R. W. J. Org. Chem. 1996, 61, 6331. Yun, W.; Mohan, R. Tetrahedron Letters 1996, 37, 7189.
3. 3. Desphande, M. S. Tetrahedron Letters 1994, 35, 5613. Kuo-Long, Y.; Desphande, M. S.; Dolatrai, M. V. Tetrahedron Letters 1994, 35, 8919. Frenette, R.; Friesen, R. W. Tetrahedron Letters 1994, 35, 9177. Forman, F. W.; Sucholeiki, I. J. Org. Chem. 1995, 60, 523. Plunkett, M. J. J. Am. Chem. Soc. 1995, 117, 3306. Hiroshige, M.; Hauske, J. R.; Zhou, P. J. Am. Chem. Soc. 1995, 777, 11590. Hiroshige, M.; Hauske, J. R.; Zhou, P. Tetrahedron Letters 1995, 36, 4567. Goff, D. A.; Zukermann, R. N. J. Org. Chem. 1995, 60, 5748. Marquais, S.; Arlt, M. Tetrahedron Letters 1996, 37, 5491. Sung Koh, J.; Ellman, J. A. J. Org. Chem. 1996, 61, 4494. Guiles, J. W.; Johnson, S. G.; Murray, W. V. J. Org. Chem. 1996, 61, 5169. Brown, D. S.; Armstrong R. W. J. Org. Chem. 1996, 61, 6331. Yun, W.; Mohan, R. Tetrahedron Letters 1996, 37, 7189.
4. 3. Desphande, M. S. Tetrahedron Letters 1994, 35, 5613. Kuo-Long, Y.; Desphande, M. S.; Dolatrai, M. V. Tetrahedron Letters 1994, 35, 8919. Frenette, R.; Friesen, R. W. Tetrahedron Letters 1994, 35, 9177. Forman, F. W.; Sucholeiki, I. J. Org. Chem. 1995, 60, 523. Plunkett, M. J. J. Am. Chem. Soc. 1995, 117, 3306. Hiroshige, M.; Hauske, J. R.; Zhou, P. J. Am. Chem. Soc. 1995, 777, 11590. Hiroshige, M.; Hauske, J. R.; Zhou, P. Tetrahedron Letters 1995, 36, 4567. Goff, D. A.; Zukermann, R. N. J. Org. Chem. 1995, 60, 5748. Marquais, S.; Arlt, M. Tetrahedron Letters 1996, 37, 5491. Sung Koh, J.; Ellman, J. A. J. Org. Chem. 1996, 61, 4494. Guiles, J. W.; Johnson, S. G.; Murray, W. V. J. Org. Chem. 1996, 61, 5169. Brown, D. S.; Armstrong R. W. J. Org. Chem. 1996, 61, 6331. Yun, W.; Mohan, R. Tetrahedron Letters 1996, 37, 7189.
5. 3. Desphande, M. S. Tetrahedron Letters 1994, 35, 5613. Kuo-Long, Y.; Desphande, M. S.; Dolatrai, M. V. Tetrahedron Letters 1994, 35, 8919. Frenette, R.; Friesen, R. W. Tetrahedron Letters 1994, 35, 9177. Forman, F. W.; Sucholeiki, I. J. Org. Chem. 1995, 60, 523. Plunkett, M. J. J. Am. Chem. Soc. 1995, 117, 3306. Hiroshige, M.; Hauske, J. R.; Zhou, P. J. Am. Chem. Soc. 1995, 777, 11590. Hiroshige, M.; Hauske, J. R.; Zhou, P. Tetrahedron Letters 1995, 36, 4567. Goff, D. A.; Zukermann, R. N. J. Org. Chem. 1995, 60, 5748. Marquais, S.; Arlt, M. Tetrahedron Letters 1996, 37, 5491. Sung Koh, J.; Ellman, J. A. J. Org. Chem. 1996, 61, 4494. Guiles, J. W.; Johnson, S. G.; Murray, W. V. J. Org. Chem. 1996, 61, 5169. Brown, D. S.; Armstrong R. W. J. Org. Chem. 1996, 61, 6331. Yun, W.; Mohan, R. Tetrahedron Letters 1996, 37, 7189.
6. 3. Desphande, M. S. Tetrahedron Letters 1994, 35, 5613. Kuo-Long, Y.; Desphande, M. S.; Dolatrai, M. V. Tetrahedron Letters 1994, 35, 8919. Frenette, R.; Friesen, R. W. Tetrahedron Letters 1994, 35, 9177. Forman, F. W.; Sucholeiki, I. J. Org. Chem. 1995, 60, 523. Plunkett, M. J. J. Am. Chem. Soc. 1995, 117, 3306. Hiroshige, M.; Hauske, J. R.; Zhou, P. J. Am. Chem. Soc. 1995, 777, 11590. Hiroshige, M.; Hauske, J. R.; Zhou, P. Tetrahedron Letters 1995, 36, 4567. Goff, D. A.; Zukermann, R. N. J. Org. Chem. 1995, 60, 5748. Marquais, S.; Arlt, M. Tetrahedron Letters 1996, 37, 5491. Sung Koh, J.; Ellman, J. A. J. Org. Chem. 1996, 61, 4494. Guiles, J. W.; Johnson, S. G.; Murray, W. V. J. Org. Chem. 1996, 61, 5169. Brown, D. S.; Armstrong R. W. J. Org. Chem. 1996, 61, 6331. Yun, W.; Mohan, R. Tetrahedron Letters 1996, 37, 7189.
7. 3. Desphande, M. S. Tetrahedron Letters 1994, 35, 5613. Kuo-Long, Y.; Desphande, M. S.; Dolatrai, M. V. Tetrahedron Letters 1994, 35, 8919. Frenette, R.; Friesen, R. W. Tetrahedron Letters 1994, 35, 9177. Forman, F. W.; Sucholeiki, I. J. Org. Chem. 1995, 60, 523. Plunkett, M. J. J. Am. Chem. Soc. 1995, 117, 3306. Hiroshige, M.; Hauske, J. R.; Zhou, P. J. Am. Chem. Soc. 1995, 777, 11590. Hiroshige, M.; Hauske, J. R.; Zhou, P. Tetrahedron Letters 1995, 36, 4567. Goff, D. A.; Zukermann, R. N. J. Org. Chem. 1995, 60, 5748. Marquais, S.; Arlt, M. Tetrahedron Letters 1996, 37, 5491. Sung Koh, J.; Ellman, J. A. J. Org. Chem. 1996, 61, 4494. Guiles, J. W.; Johnson, S. G.; Murray, W. V. J. Org. Chem. 1996, 61, 5169. Brown, D. S.; Armstrong R. W. J. Org. Chem. 1996, 61, 6331. Yun, W.; Mohan, R. Tetrahedron Letters 1996, 37, 7189.
8. 3. Desphande, M. S. Tetrahedron Letters 1994, 35, 5613. Kuo-Long, Y.; Desphande, M. S.; Dolatrai, M. V. Tetrahedron Letters 1994, 35, 8919. Frenette, R.; Friesen, R. W. Tetrahedron Letters 1994, 35, 9177. Forman, F. W.; Sucholeiki, I. J. Org. Chem. 1995, 60, 523. Plunkett, M. J. J. Am. Chem. Soc. 1995, 117, 3306. Hiroshige, M.; Hauske, J. R.; Zhou, P. J. Am. Chem. Soc. 1995, 777, 11590. Hiroshige, M.; Hauske, J. R.; Zhou, P. Tetrahedron Letters 1995, 36, 4567. Goff, D. A.; Zukermann, R. N. J. Org. Chem. 1995, 60, 5748. Marquais, S.; Arlt, M. Tetrahedron Letters 1996, 37, 5491. Sung Koh, J.; Ellman, J. A. J. Org. Chem. 1996, 61, 4494. Guiles, J. W.; Johnson, S. G.; Murray, W. V. J. Org. Chem. 1996, 61, 5169. Brown, D. S.; Armstrong R. W. J. Org. Chem. 1996, 61, 6331. Yun, W.; Mohan, R. Tetrahedron Letters 1996, 37, 7189.
9. 3. Desphande, M. S. Tetrahedron Letters 1994, 35, 5613. Kuo-Long, Y.; Desphande, M. S.; Dolatrai, M. V. Tetrahedron Letters 1994, 35, 8919. Frenette, R.; Friesen, R. W. Tetrahedron Letters 1994, 35, 9177. Forman, F. W.; Sucholeiki, I. J. Org. Chem. 1995, 60, 523. Plunkett, M. J. J. Am. Chem. Soc. 1995, 117, 3306. Hiroshige, M.; Hauske, J. R.; Zhou, P. J. Am. Chem. Soc. 1995, 777, 11590. Hiroshige, M.; Hauske, J. R.; Zhou, P. Tetrahedron Letters 1995, 36, 4567. Goff, D. A.; Zukermann, R. N. J. Org. Chem. 1995, 60, 5748. Marquais, S.; Arlt, M. Tetrahedron Letters 1996, 37, 5491. Sung Koh, J.; Ellman, J. A. J. Org. Chem. 1996, 61, 4494. Guiles, J. W.; Johnson, S. G.; Murray, W. V. J. Org. Chem. 1996, 61, 5169. Brown, D. S.; Armstrong R. W. J. Org. Chem. 1996, 61, 6331. Yun, W.; Mohan, R. Tetrahedron Letters 1996, 37, 7189.
10. 3. Desphande, M. S. Tetrahedron Letters 1994, 35, 5613. Kuo-Long, Y.; Desphande, M. S.; Dolatrai, M. V. Tetrahedron Letters 1994, 35, 8919. Frenette, R.; Friesen, R. W. Tetrahedron Letters 1994, 35, 9177. Forman, F. W.; Sucholeiki, I. J. Org. Chem. 1995, 60, 523. Plunkett, M. J. J. Am. Chem. Soc. 1995, 117, 3306. Hiroshige, M.; Hauske, J. R.; Zhou, P. J. Am. Chem. Soc. 1995, 777, 11590. Hiroshige, M.; Hauske, J. R.; Zhou, P. Tetrahedron Letters 1995, 36, 4567. Goff, D. A.; Zukermann, R. N. J. Org. Chem. 1995, 60, 5748. Marquais, S.; Arlt, M. Tetrahedron Letters 1996, 37, 5491. Sung Koh, J.; Ellman, J. A. J. Org. Chem. 1996, 61, 4494. Guiles, J. W.; Johnson, S. G.; Murray, W. V. J. Org. Chem. 1996, 61, 5169. Brown, D. S.; Armstrong R. W. J. Org. Chem. 1996, 61, 6331. Yun, W.; Mohan, R. Tetrahedron Letters 1996, 37, 7189.
11. 3. Desphande, M. S. Tetrahedron Letters 1994, 35, 5613. Kuo-Long, Y.; Desphande, M. S.; Dolatrai, M. V. Tetrahedron Letters 1994, 35, 8919. Frenette, R.; Friesen, R. W. Tetrahedron Letters 1994, 35, 9177. Forman, F. W.; Sucholeiki, I. J. Org. Chem. 1995, 60, 523. Plunkett, M. J. J. Am. Chem. Soc. 1995, 117, 3306. Hiroshige, M.; Hauske, J. R.; Zhou, P. J. Am. Chem. Soc. 1995, 777, 11590. Hiroshige, M.; Hauske, J. R.; Zhou, P. Tetrahedron Letters 1995, 36, 4567. Goff, D. A.; Zukermann, R. N. J. Org. Chem. 1995, 60, 5748. Marquais, S.; Arlt, M. Tetrahedron Letters 1996, 37, 5491. Sung Koh, J.; Ellman, J. A. J. Org. Chem. 1996, 61, 4494. Guiles, J. W.; Johnson, S. G.; Murray, W. V. J. Org. Chem. 1996, 61, 5169. Brown, D. S.; Armstrong R. W. J. Org. Chem. 1996, 61, 6331. Yun, W.; Mohan, R. Tetrahedron Letters 1996, 37, 7189.
12. 3. Desphande, M. S. Tetrahedron Letters 1994, 35, 5613. Kuo-Long, Y.; Desphande, M. S.; Dolatrai, M. V. Tetrahedron Letters 1994, 35, 8919. Frenette, R.; Friesen, R. W. Tetrahedron Letters 1994, 35, 9177. Forman, F. W.; Sucholeiki, I. J. Org. Chem. 1995, 60, 523. Plunkett, M. J. J. Am. Chem. Soc. 1995, 117, 3306. Hiroshige, M.; Hauske, J. R.; Zhou, P. J. Am. Chem. Soc. 1995, 777, 11590. Hiroshige, M.; Hauske, J. R.; Zhou, P. Tetrahedron Letters 1995, 36, 4567. Goff, D. A.; Zukermann, R. N. J. Org. Chem. 1995, 60, 5748. Marquais, S.; Arlt, M. Tetrahedron Letters 1996, 37, 5491. Sung Koh, J.; Ellman, J. A. J. Org. Chem. 1996, 61, 4494. Guiles, J. W.; Johnson, S. G.; Murray, W. V. J. Org. Chem. 1996, 61, 5169. Brown, D. S.; Armstrong R. W. J. Org. Chem. 1996, 61, 6331. Yun, W.; Mohan, R. Tetrahedron Letters 1996, 37, 7189.
13. 3. Desphande, M. S. Tetrahedron Letters 1994, 35, 5613. Kuo-Long, Y.; Desphande, M. S.; Dolatrai, M. V. Tetrahedron Letters 1994, 35, 8919. Frenette, R.; Friesen, R. W. Tetrahedron Letters 1994, 35, 9177. Forman, F. W.; Sucholeiki, I. J. Org. Chem. 1995, 60, 523. Plunkett, M. J. J. Am. Chem. Soc. 1995, 117, 3306. Hiroshige, M.; Hauske, J. R.; Zhou, P. J. Am. Chem. Soc. 1995, 777, 11590. Hiroshige, M.; Hauske, J. R.; Zhou, P. Tetrahedron Letters 1995, 36, 4567. Goff, D. A.; Zukermann, R. N. J. Org. Chem. 1995, 60, 5748. Marquais, S.; Arlt, M. Tetrahedron Letters 1996, 37, 5491. Sung Koh, J.; Ellman, J. A. J. Org. Chem. 1996, 61, 4494. Guiles, J. W.; Johnson, S. G.; Murray, W. V. J. Org. Chem. 1996, 61, 5169. Brown, D. S.; Armstrong R. W. J. Org. Chem. 1996, 61, 6331. Yun, W.; Mohan, R. Tetrahedron Letters 1996, 37, 7189.
14. 3. Desphande, M. S. Tetrahedron Letters 1994, 35, 5613. Kuo-Long, Y.; Desphande, M. S.; Dolatrai, M. V. Tetrahedron Letters 1994, 35, 8919. Frenette, R.; Friesen, R. W. Tetrahedron Letters 1994, 35, 9177. Forman, F. W.; Sucholeiki, I. J. Org. Chem. 1995, 60, 523. Plunkett, M. J. J. Am. Chem. Soc. 1995, 117, 3306. Hiroshige, M.; Hauske, J. R.; Zhou, P. J. Am. Chem. Soc. 1995, 777, 11590. Hiroshige, M.; Hauske, J. R.; Zhou, P. Tetrahedron Letters 1995, 36, 4567. Goff, D. A.; Zukermann, R. N. J. Org. Chem. 1995, 60, 5748. Marquais, S.; Arlt, M. Tetrahedron Letters 1996, 37, 5491. Sung Koh, J.; Ellman, J. A. J. Org. Chem. 1996, 61, 4494. Guiles, J. W.; Johnson, S. G.; Murray, W. V. J. Org. Chem. 1996, 61, 5169. Brown, D. S.; Armstrong R. W. J. Org. Chem. 1996, 61, 6331. Yun, W.; Mohan, R. Tetrahedron Letters 1996, 37, 7189.
15. 4. See accompanying paper.
16. 5. For recent examples of palladium catalysed synthesis of indoles, see Ezquerra, J.; Pedregal, C.; Lamas, J. M.; Barluenga, J.; Perez, M.; Garcia-Martin, M. A.; Gonzalez, J. M. J. Org. Chem. 1996, 61, 5804, and references herein.
17. 6. Sakamoto, T.; Kondo, Y; Iwashita, S.; Nagano, T.; Yamanaka, H. Chem. Pharm. Bull. 1988, 36, 1305.
18. 7. Villemin, D.; Goussu, D. Heterocycles 1989, 29, 1255.
19. 8. Candiani, I.; DeBernardinis, S.; Cabri, W.; Marchi, M.; Bedeschi, A.; Penco, S. Synlett 1993, 3, 269.
20. 2 (13g) was added. The reaction mixture was stirred overnight, and the solid was collected by filtration, washed, and dried. The crude iodo derivative (6.5g) was used in the next step. The solid was dissolved in acetic acid (80mL) and acetic anydride (4.7mL) was added. The mixture was starred overnight, concentrated in vacuo, filtered, washed with water, and dried to afford 6.2g of the acid (1b). The acetylated product was then methylated with diazomethane. 1a and 1b gave satisfactory analysis.
21. 10. Upon cleavage of the resin in the conditions described, 5 affords the acetylenic derivative 8 (scheme shown below). The amount of 8 is therefore a direct measure of the efficiency of the cyclisation step. (figure presented)