Cross-coupling methods for the large-scale preparation of an imidazole - Thienopyridine: Synthesis of [2-(3-methyl-3H-imidazol-4-yl)-thieno[3,2-b]pyridin-7-yl] -(2-methyl-1H-indol-5-yl)-amine

Organic Process Research and Development

Volumn 7, Issue 5, 2003, Pages 676-683

  Ragan, J A ^a   Raggon, J W ^a   Hill, P D ^a   Jones, B P ^a   McDermott, R E ^a   Munchhof, M J ^a   Marx, M A ^a   Casavant, J M ^a   Cooper, B A ^a   Doty, J L ^a   Lu, Y ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

5 (TRIBUTYLSTANNYL) 1 METHYLIMIDAZOLE; [2 (3 METHYL 3H IMIDAZOL 4 YL)THIENO[3,2 B]PYRIDIN 7 YL](2 METHYL 1H INDOL 5 YL)AMINE; IMIDAZOLE DERIVATIVE; IODOTHIENOPYRIDINE; ORGANOTIN COMPOUND; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG; ZINC DERIVATIVE;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; EVALUATION; SCALE UP; TECHNIQUE;

EID: 0141890132     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op0340457     Document Type: Article

References (35)

1. (a) Fan, T. P. D.; Jaggar, R.; Bicknell, R. Trends Pharmacol. Sci. 1995, 16, 57-66.
2. (b) Folkman, J. Nat. Med. 1995, 1, 27-31.
3. (a) Barker, J. M.; Huddleston, P. R.; Holmes, D.; Keenan, G. J.; Wright, B. J. Chem. Res. Miniprint 1984, 771-795.
4. (b) Barker, J. M.; Huddleston, P. R.; Holmes, D.; Keenan, G. J. J. Chem. Res. Miniprint 1982, 1726-1746.
5. Barker, J. M.; Huddleston, P. R.; Wood, M. L. Synth. Commun. 1995, 25, 3729-3734.
6. (a) Cassis, R.; Tapia, R.; Valderrama, J. A. Synth. Commun. 1985, 15, 125-134.
7. (b) Andrew, R. G.; Raphael, R. A. Tetrahedron 1987, 43, 4803-4816.
8. (c) Moron, J.; Huel, C.; Bisagni, E. Heterocycles 1993, 36, 2753-2764.
9. (d) Marcos, A.; Pedregal, C.; Avendano, C. Tetrahedron 1995, 51, 1763-1774.
10. (e) Toedter, C.; Lackner, H. Synthesis 1997, 567-572.
11. For reviews, see: (a) Mitchell, T. N. In Metal-catalyzed Cross-coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH Verlag: Weinheim, Germany, 1998; Chapter 4. (b) Farina, V.; Krishnamurthy, V.; Scott, W. J. Org. React. 1997, 50, 1-652. (c) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508-524.
12. For reviews, see: (a) Mitchell, T. N. In Metal-catalyzed Cross-coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH Verlag: Weinheim, Germany, 1998; Chapter 4. (b) Farina, V.; Krishnamurthy, V.; Scott, W. J. Org. React. 1997, 50, 1-652. (c) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508-524.
13. For reviews, see: (a) Mitchell, T. N. In Metal-catalyzed Cross-coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH Verlag: Weinheim, Germany, 1998; Chapter 4. (b) Farina, V.; Krishnamurthy, V.; Scott, W. J. Org. React. 1997, 50, 1-652. (c) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508-524.
14. Similar Stille and Negishi couplings with 4-susbstituted N-alkylimidazoles (vs 5-substituted in the present study) have been reported: (a) Jetter, M. C.; Reitz, A. B. Synthesis 1998, 829-831. (b) Cliff, M. D.; Pyne, S. G. Tetrahedron 1996, 52, 13703-13712.
15. Similar Stille and Negishi couplings with 4-susbstituted N-alkylimidazoles (vs 5-substituted in the present study) have been reported: (a) Jetter, M. C.; Reitz, A. B. Synthesis 1998, 829-831. (b) Cliff, M. D.; Pyne, S. G. Tetrahedron 1996, 52, 13703-13712.
16. For reviews, see: (a) Negishi, E.; Liu, F. In Metal-catalyzed Cross-coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH Verlag: Weinheim, Germany, 1998; Chapter 1. (b) Erdik, E. Tetrahedron 1992, 48, 9577-9648.
17. For reviews, see: (a) Negishi, E.; Liu, F. In Metal-catalyzed Cross-coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH Verlag: Weinheim, Germany, 1998; Chapter 1. (b) Erdik, E. Tetrahedron 1992, 48, 9577-9648.
18. (a) Brase, S.; de Meijere, A. In Metal-catalyzed Cross-coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH Verlag: Weinheim, Germany, 1998; Chapter 3.
19. (b) Pivsa-Art, S.; Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Bull. Chem. Soc. Jpn. 1998, 71, 467.
20. (c) Aoyagi, Y.; Inoue, A.; Koizumi, I.; Hashimoto, R.; Tokunaga, K.; Gohma, K.; Komatsu, J.; Sekine, K.; Miyafuji, A.; Kunoh, J.; Honma, R. Akita, Y., Ohta, A. Heterocycles 1992, 33, 257.
21. Gurtler, C.; Buchwald, S. L. Chem. Eur. J. 1999, 5, 3107-3112.
22. For reviews, see: (a) Hiyama, T. in Metal-catalyzed Cross-coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH Verlag: Weinheim, Germany, 1998; Chapter 10. (b) Hiyama, T.; Hatanaka, Y. Pure Appl. Chem. 1994, 66, 1471-1478.
23. For reviews, see: (a) Hiyama, T. in Metal-catalyzed Cross-coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH Verlag: Weinheim, Germany, 1998; Chapter 10. (b) Hiyama, T.; Hatanaka, Y. Pure Appl. Chem. 1994, 66, 1471-1478.
24. For reviews, see (a) Suzuki, A. J. Organomet. Chem. 1999, 576, 147-168. (b) Miyaura, N. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI, London, 1998; Vol. 6, pp 187-243. (c) Suzuki, A. In Metal-catalyzed Cross-coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH Verlag: Weinheim, Germany, 1998; Chapter 2. (d) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483.
25. For reviews, see (a) Suzuki, A. J. Organomet. Chem. 1999, 576, 147-168. (b) Miyaura, N. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI, London, 1998; Vol. 6, pp 187-243. (c) Suzuki, A. In Metal-catalyzed Cross-coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH Verlag: Weinheim, Germany, 1998; Chapter 2. (d) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483.
26. For reviews, see (a) Suzuki, A. J. Organomet. Chem. 1999, 576, 147-168. (b) Miyaura, N. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI, London, 1998; Vol. 6, pp 187-243. (c) Suzuki, A. In Metal-catalyzed Cross-coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH Verlag: Weinheim, Germany, 1998; Chapter 2. (d) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483.
27. For reviews, see (a) Suzuki, A. J. Organomet. Chem. 1999, 576, 147-168. (b) Miyaura, N. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI, London, 1998; Vol. 6, pp 187-243. (c) Suzuki, A. In Metal-catalyzed Cross-coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH Verlag: Weinheim, Germany, 1998; Chapter 2. (d) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483.
28. (a) Tamao, K.; Kodama, S.; Nakajima, I.; Kumada, M.; Minato, A.; Suzuki, K. Tetrahedron 1982, 38, 3347-3354.
29. Kobayashi, Y.; Ikeda, E. J. Chem. Soc., Chem. Commun. 1994, 1789.
30. Mowery, M. E.; DeShong, P. J. Org. Chem. 1999, 64, 1684-1688.
31. 4) × (equiv cat.) = (118 × 1.1)/(295 × 1.0) + (370 x 1.1) + (1155 × 0.05) = 0.17 (17%) = 170 000 ppm.
32. Gaare, K.; Repstad, T.; Benneche, T.; Undheim, K. Acta Chem. Scand. 1993, 47, 57-62.
33. (a) Barker, J. M.; Huddleston, P. R.; Holmes, D.; Keenan, G. J.; Wright, B. J. Chem. Res. Miniprint 1984, 771-795.
34. (b) Cutler, R. A.; Surrey, A. R. J. Am. Chem. Soc. 1955, 77, 2441-2444.
35. Walters, M. A.; Lee, M. D. Tetrahedron Lett. 1994, 35, 8307-8310.