Expedient synthesis of secondary amines bound to indole resin and cleavage of resin-bound urea, amide and sulfonamide under mild conditions

Tetrahedron Letters

Volumn 44, Issue 32, 2003, Pages 6099-6102

  Bhattacharyya, Sukanta ^a   Gooding, Owen W ^a   Labadie, Jeff ^a  

^a Argonaut Technologies   (United States)

Author keywords

Indole aldehyde resin; Primary amines; Reductive amination

Indexed keywords

ALDEHYDE; AMIDE; AMINE; BORON DERIVATIVE; INDOLE DERIVATIVE; RESIN; SODIUM DERIVATIVE; SULFONAMIDE; TITANIUM DERIVATIVE; TRIFLUOROACETIC ACID; UREA DERIVATIVE;

ARTICLE; CHEMICAL BOND; SOLID; SYNTHESIS;

EID: 0037629632     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01456-4     Document Type: Article

References (24)

1. Swayze E.E. Tetrahedron Lett. 38:1997;8465.
2. Ngu M., Patel D.V. Tetrahedron Lett. 38:1997;973.
3. Fivush A.M., Willson T.M. Tetrahedron Lett. 38:1997;7151.
4. Sarantakis D., Bicksler J.J. Tetrahedron Lett. 38:1997;7325.
5. Bilodeau M.T., Cunningham A.M. J. Org. Chem. 63:1998;2800.
6. Harikrishanan L.S., Hollis Showalter H.D. Synlett. 2000;1339.
7. Makino S., Nakanishi E., Tsuji T. J. Comb. Chem. 5:2003;73.
8. Boojamra C.G., Burow K.M., Thomson L.A., Ellman J. J. Org. Chem. 62:1997;1240.
9. Estep K.G., Neipp C.E., Stramiello L.M.S., Adam M.D., Allen M.P., Robinson S., Roskamp E.J. J. Org. Chem. 63:1998;5300.
10. For examples, see: (a) Bhattacharyya, S. Tetrahedron Lett. 1994, 35, 2401; (b) Bhattacharyya, S. J. Org. Chem. 1995, 60, 4928; (c) Bhattacharyya, S.; Chatterjee, A.; Williamson, J. S. Synlett 1995, 1079; (d) Neidigh, K. A.; Avery, M. A.; Williamson, J. S.; Bhattacharyya, S. J. Chem. Soc., Perkin Trans. 1 1998, 2527; (e) Bhattacharyya, S.; Neidigh, K. A.; Avery, M. A.; Williamson, J. S. Synlett 1999, 1781.
11. For examples, see: (a) Bhattacharyya, S. Tetrahedron Lett. 1994, 35, 2401; (b) Bhattacharyya, S. J. Org. Chem. 1995, 60, 4928; (c) Bhattacharyya, S.; Chatterjee, A.; Williamson, J. S. Synlett 1995, 1079; (d) Neidigh, K. A.; Avery, M. A.; Williamson, J. S.; Bhattacharyya, S. J. Chem. Soc., Perkin Trans. 1 1998, 2527; (e) Bhattacharyya, S.; Neidigh, K. A.; Avery, M. A.; Williamson, J. S. Synlett 1999, 1781.
12. For examples, see: (a) Bhattacharyya, S. Tetrahedron Lett. 1994, 35, 2401; (b) Bhattacharyya, S. J. Org. Chem. 1995, 60, 4928; (c) Bhattacharyya, S.; Chatterjee, A.; Williamson, J. S. Synlett 1995, 1079; (d) Neidigh, K. A.; Avery, M. A.; Williamson, J. S.; Bhattacharyya, S. J. Chem. Soc., Perkin Trans. 1 1998, 2527; (e) Bhattacharyya, S.; Neidigh, K. A.; Avery, M. A.; Williamson, J. S. Synlett 1999, 1781.
13. For examples, see: (a) Bhattacharyya, S. Tetrahedron Lett. 1994, 35, 2401; (b) Bhattacharyya, S. J. Org. Chem. 1995, 60, 4928; (c) Bhattacharyya, S.; Chatterjee, A.; Williamson, J. S. Synlett 1995, 1079; (d) Neidigh, K. A.; Avery, M. A.; Williamson, J. S.; Bhattacharyya, S. J. Chem. Soc., Perkin Trans. 1 1998, 2527; (e) Bhattacharyya, S.; Neidigh, K. A.; Avery, M. A.; Williamson, J. S. Synlett 1999, 1781.
14. For examples, see: (a) Bhattacharyya, S. Tetrahedron Lett. 1994, 35, 2401; (b) Bhattacharyya, S. J. Org. Chem. 1995, 60, 4928; (c) Bhattacharyya, S.; Chatterjee, A.; Williamson, J. S. Synlett 1995, 1079; (d) Neidigh, K. A.; Avery, M. A.; Williamson, J. S.; Bhattacharyya, S. J. Chem. Soc., Perkin Trans. 1 1998, 2527; (e) Bhattacharyya, S.; Neidigh, K. A.; Avery, M. A.; Williamson, J. S. Synlett 1999, 1781.
15. Szardenings A.K., Burkoth T.S., Look G.C., Campbell D.A. J. Org. Chem. 61:1996;6720.
16. Matthews J., Rivero R.A. J. Org. Chem. 62:1997;6090.
17. Indole-aldehyde resin, PS-Indole-CHO was obtained from Argonaut Technologies.
18. 4 (2 ml, ca. 0.75 M) in absolute EtOH was added and the resulting mixture stirred for a further period of 2 h. The supernatant liquid was drained off and the resin washed with THF (8 mL×2), MeOH (8 mL×3) and DCM (8 mL×2).
19. Khan N.M., Arumugam V., Balasubramanium S. Tetrahedron Lett. 37:1996;4819.
20. 3CN (1.0 mL, 1 M) in THF and acetic acid (0.1 mL) were added. The resulting mixture was stirred for 2 h. The supernatant liquid was drained off and the resin washed with THF (8 mL×2), MeOH (8 mL×3) and DCM (8 mL×2).
21. To a suspension of the resin-bound secondary amine (0.1 g) in DCM (2 mL) and triethylamine (1 mL) was added an acid chloride/sulfonyl chloride (0.5 mmol). The resulting mixture was agitated overnight at ambient temperature. The supernatant liquid is drained off and the resin washed with DMF, MeOH and DCM.
22. To a suspension of the resin-bound secondary amine (0.1 g) in DCM (2 mL) was added an isocyanate (0.5 mmol). The resulting mixture was agitated overnight at ambient temperature. The supernatant liquid is drained off and the resin washed with DMF, MeOH and DCM.
23. 1H NMR spectral analysis.
24. 3, 300 MHz): 2.8 (t, 2H, J=7 Hz), 3.4 (t, 2H, J=7 Hz), 4.26 (s, 2H), 7.06-7.4 (m, 10H).