Novel N-aryl and N-heteroaryl sulfamide synthesis via palladium cross coupling

Organic Letters

Volumn 6, Issue 16, 2004, Pages 2705-2708

  Alcaraz, Lilian ^a   Bennion, Colin ^a   Morris, James ^a   Meghani, Premji ^a   Thom, Stephen M ^a  

^a ASTRAZENECA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

FUNCTIONAL GROUP; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SULFAMIDE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; COMBINATORIAL CHEMISTRY; CROSS COUPLING REACTION; MOLECULAR INTERACTION; REACTION ANALYSIS; SULFONATION;

EID: 4344607674     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049091l     Document Type: Article

References (37)

1. For selected examples from recent literature, see: (a) Zhong, J.; Gan, X. Bioorg. Med. Chem. 2004, 12, 589-593. (b) Collins, I. J.; Cooper, L. C. WO-2003093264, 2003; Chem. Abstr. 2003, 139, 381492. (c) Kadow, J. F.; Regueiro-Ren, A.; Xue, Q. M. WO-2004000210, 2003; Chem. Abstr. 2003, 140, 59662. (d) Cherney, R. J.; King, B. W. WO-2002028846, 2002; Chem. Abstr. 2002, 136, 309923. (e) Schaal, W.; Karlsson, A.; Ahlsén, G.; Lindberg, J.; Andersson, H. O.; Danielson, U. H.; Classon, B.; Unge, T.; Samuelsson, B.; Hultén, J.; Hallberg, A.; Karlén, A. J. Med. Chem. 2001, 44, 155-169. (f) Groutas, W. C.; He, S.; Kuang, R.; Ruan, S.; Tu, J.; Chan, H.-K. Bioorg. Med. Chem. 2001, 9, 1543-1548. (g) Shih, N.-Y.; Shue, H.-J.; Reichard, G. A.; Paliwal, S.; Blynthin, D. J.; Piwinski, J. J.; Xiao, D.; Chen, X. WO-2001044200, 2001; Chem. Abstr. 2001, 135, 61331. (h) Kuang, R.; Epp, J. B.; Ruan, S.; Chong, L. S.; Venkataraman, R.; Tu, J.; He, S.; Truong, T. M.; Groutas, W. C. Bioorg. Med. Chem. 2000, 8, 1005-1016. (i) He, S.; Kuang, R.; Venkataraman, R.; Tu, J.; Truong, T. M.; Chan, H.-K.; Groutas, W. C. Bioorg. Med. Chem. 2000, 8, 1713-11717. (j) Martinez, A.; Gil, C.; Perez, C.; Castro, A.; Prieto, C.; Otero, J.; Andrei, G.; Snoeck, R.; Balazarini, J.; De Clerk, E. J. Med. Chem. 2000, 43, 3267-3273. (k) Benson, G. M.; Rutledge, M. C.; Widdowson, K. L. WO-2000076501, 2000; Chem. Abstr. 2001, 134, 56675. (l) Lee, C. H.; Kohn, H. J. Pharm. Sci. 1990, 79, 716-718.
2. For selected examples from recent literature, see: (a) Zhong, J.; Gan, X. Bioorg. Med. Chem. 2004, 12, 589-593. (b) Collins, I. J.; Cooper, L. C. WO-2003093264, 2003; Chem. Abstr. 2003, 139, 381492. (c) Kadow, J. F.; Regueiro-Ren, A.; Xue, Q. M. WO-2004000210, 2003; Chem. Abstr. 2003, 140, 59662. (d) Cherney, R. J.; King, B. W. WO-2002028846, 2002; Chem. Abstr. 2002, 136, 309923. (e) Schaal, W.; Karlsson, A.; Ahlsén, G.; Lindberg, J.; Andersson, H. O.; Danielson, U. H.; Classon, B.; Unge, T.; Samuelsson, B.; Hultén, J.; Hallberg, A.; Karlén, A. J. Med. Chem. 2001, 44, 155-169. (f) Groutas, W. C.; He, S.; Kuang, R.; Ruan, S.; Tu, J.; Chan, H.-K. Bioorg. Med. Chem. 2001, 9, 1543-1548. (g) Shih, N.-Y.; Shue, H.-J.; Reichard, G. A.; Paliwal, S.; Blynthin, D. J.; Piwinski, J. J.; Xiao, D.; Chen, X. WO-2001044200, 2001; Chem. Abstr. 2001, 135, 61331. (h) Kuang, R.; Epp, J. B.; Ruan, S.; Chong, L. S.; Venkataraman, R.; Tu, J.; He, S.; Truong, T. M.; Groutas, W. C. Bioorg. Med. Chem. 2000, 8, 1005-1016. (i) He, S.; Kuang, R.; Venkataraman, R.; Tu, J.; Truong, T. M.; Chan, H.-K.; Groutas, W. C. Bioorg. Med. Chem. 2000, 8, 1713-11717. (j) Martinez, A.; Gil, C.; Perez, C.; Castro, A.; Prieto, C.; Otero, J.; Andrei, G.; Snoeck, R.; Balazarini, J.; De Clerk, E. J. Med. Chem. 2000, 43, 3267-3273. (k) Benson, G. M.; Rutledge, M. C.; Widdowson, K. L. WO-2000076501, 2000; Chem. Abstr. 2001, 134, 56675. (l) Lee, C. H.; Kohn, H. J. Pharm. Sci. 1990, 79, 716-718.
3. For selected examples from recent literature, see: (a) Zhong, J.; Gan, X. Bioorg. Med. Chem. 2004, 12, 589-593. (b) Collins, I. J.; Cooper, L. C. WO-2003093264, 2003; Chem. Abstr. 2003, 139, 381492. (c) Kadow, J. F.; Regueiro-Ren, A.; Xue, Q. M. WO-2004000210, 2003; Chem. Abstr. 2003, 140, 59662. (d) Cherney, R. J.; King, B. W. WO-2002028846, 2002; Chem. Abstr. 2002, 136, 309923. (e) Schaal, W.; Karlsson, A.; Ahlsén, G.; Lindberg, J.; Andersson, H. O.; Danielson, U. H.; Classon, B.; Unge, T.; Samuelsson, B.; Hultén, J.; Hallberg, A.; Karlén, A. J. Med. Chem. 2001, 44, 155-169. (f) Groutas, W. C.; He, S.; Kuang, R.; Ruan, S.; Tu, J.; Chan, H.-K. Bioorg. Med. Chem. 2001, 9, 1543-1548. (g) Shih, N.-Y.; Shue, H.-J.; Reichard, G. A.; Paliwal, S.; Blynthin, D. J.; Piwinski, J. J.; Xiao, D.; Chen, X. WO-2001044200, 2001; Chem. Abstr. 2001, 135, 61331. (h) Kuang, R.; Epp, J. B.; Ruan, S.; Chong, L. S.; Venkataraman, R.; Tu, J.; He, S.; Truong, T. M.; Groutas, W. C. Bioorg. Med. Chem. 2000, 8, 1005-1016. (i) He, S.; Kuang, R.; Venkataraman, R.; Tu, J.; Truong, T. M.; Chan, H.-K.; Groutas, W. C. Bioorg. Med. Chem. 2000, 8, 1713-11717. (j) Martinez, A.; Gil, C.; Perez, C.; Castro, A.; Prieto, C.; Otero, J.; Andrei, G.; Snoeck, R.; Balazarini, J.; De Clerk, E. J. Med. Chem. 2000, 43, 3267-3273. (k) Benson, G. M.; Rutledge, M. C.; Widdowson, K. L. WO-2000076501, 2000; Chem. Abstr. 2001, 134, 56675. (l) Lee, C. H.; Kohn, H. J. Pharm. Sci. 1990, 79, 716-718.
4. For selected examples from recent literature, see: (a) Zhong, J.; Gan, X. Bioorg. Med. Chem. 2004, 12, 589-593. (b) Collins, I. J.; Cooper, L. C. WO-2003093264, 2003; Chem. Abstr. 2003, 139, 381492. (c) Kadow, J. F.; Regueiro-Ren, A.; Xue, Q. M. WO-2004000210, 2003; Chem. Abstr. 2003, 140, 59662. (d) Cherney, R. J.; King, B. W. WO-2002028846, 2002; Chem. Abstr. 2002, 136, 309923. (e) Schaal, W.; Karlsson, A.; Ahlsén, G.; Lindberg, J.; Andersson, H. O.; Danielson, U. H.; Classon, B.; Unge, T.; Samuelsson, B.; Hultén, J.; Hallberg, A.; Karlén, A. J. Med. Chem. 2001, 44, 155-169. (f) Groutas, W. C.; He, S.; Kuang, R.; Ruan, S.; Tu, J.; Chan, H.-K. Bioorg. Med. Chem. 2001, 9, 1543-1548. (g) Shih, N.-Y.; Shue, H.-J.; Reichard, G. A.; Paliwal, S.; Blynthin, D. J.; Piwinski, J. J.; Xiao, D.; Chen, X. WO-2001044200, 2001; Chem. Abstr. 2001, 135, 61331. (h) Kuang, R.; Epp, J. B.; Ruan, S.; Chong, L. S.; Venkataraman, R.; Tu, J.; He, S.; Truong, T. M.; Groutas, W. C. Bioorg. Med. Chem. 2000, 8, 1005-1016. (i) He, S.; Kuang, R.; Venkataraman, R.; Tu, J.; Truong, T. M.; Chan, H.-K.; Groutas, W. C. Bioorg. Med. Chem. 2000, 8, 1713-11717. (j) Martinez, A.; Gil, C.; Perez, C.; Castro, A.; Prieto, C.; Otero, J.; Andrei, G.; Snoeck, R.; Balazarini, J.; De Clerk, E. J. Med. Chem. 2000, 43, 3267-3273. (k) Benson, G. M.; Rutledge, M. C.; Widdowson, K. L. WO-2000076501, 2000; Chem. Abstr. 2001, 134, 56675. (l) Lee, C. H.; Kohn, H. J. Pharm. Sci. 1990, 79, 716-718.
5. For selected examples from recent literature, see: (a) Zhong, J.; Gan, X. Bioorg. Med. Chem. 2004, 12, 589-593. (b) Collins, I. J.; Cooper, L. C. WO-2003093264, 2003; Chem. Abstr. 2003, 139, 381492. (c) Kadow, J. F.; Regueiro-Ren, A.; Xue, Q. M. WO-2004000210, 2003; Chem. Abstr. 2003, 140, 59662. (d) Cherney, R. J.; King, B. W. WO-2002028846, 2002; Chem. Abstr. 2002, 136, 309923. (e) Schaal, W.; Karlsson, A.; Ahlsén, G.; Lindberg, J.; Andersson, H. O.; Danielson, U. H.; Classon, B.; Unge, T.; Samuelsson, B.; Hultén, J.; Hallberg, A.; Karlén, A. J. Med. Chem. 2001, 44, 155-169. (f) Groutas, W. C.; He, S.; Kuang, R.; Ruan, S.; Tu, J.; Chan, H.-K. Bioorg. Med. Chem. 2001, 9, 1543-1548. (g) Shih, N.-Y.; Shue, H.-J.; Reichard, G. A.; Paliwal, S.; Blynthin, D. J.; Piwinski, J. J.; Xiao, D.; Chen, X. WO-2001044200, 2001; Chem. Abstr. 2001, 135, 61331. (h) Kuang, R.; Epp, J. B.; Ruan, S.; Chong, L. S.; Venkataraman, R.; Tu, J.; He, S.; Truong, T. M.; Groutas, W. C. Bioorg. Med. Chem. 2000, 8, 1005-1016. (i) He, S.; Kuang, R.; Venkataraman, R.; Tu, J.; Truong, T. M.; Chan, H.-K.; Groutas, W. C. Bioorg. Med. Chem. 2000, 8, 1713-11717. (j) Martinez, A.; Gil, C.; Perez, C.; Castro, A.; Prieto, C.; Otero, J.; Andrei, G.; Snoeck, R.; Balazarini, J.; De Clerk, E. J. Med. Chem. 2000, 43, 3267-3273. (k) Benson, G. M.; Rutledge, M. C.; Widdowson, K. L. WO-2000076501, 2000; Chem. Abstr. 2001, 134, 56675. (l) Lee, C. H.; Kohn, H. J. Pharm. Sci. 1990, 79, 716-718.
6. For selected examples from recent literature, see: (a) Zhong, J.; Gan, X. Bioorg. Med. Chem. 2004, 12, 589-593. (b) Collins, I. J.; Cooper, L. C. WO-2003093264, 2003; Chem. Abstr. 2003, 139, 381492. (c) Kadow, J. F.; Regueiro-Ren, A.; Xue, Q. M. WO-2004000210, 2003; Chem. Abstr. 2003, 140, 59662. (d) Cherney, R. J.; King, B. W. WO-2002028846, 2002; Chem. Abstr. 2002, 136, 309923. (e) Schaal, W.; Karlsson, A.; Ahlsén, G.; Lindberg, J.; Andersson, H. O.; Danielson, U. H.; Classon, B.; Unge, T.; Samuelsson, B.; Hultén, J.; Hallberg, A.; Karlén, A. J. Med. Chem. 2001, 44, 155-169. (f) Groutas, W. C.; He, S.; Kuang, R.; Ruan, S.; Tu, J.; Chan, H.-K. Bioorg. Med. Chem. 2001, 9, 1543-1548. (g) Shih, N.-Y.; Shue, H.-J.; Reichard, G. A.; Paliwal, S.; Blynthin, D. J.; Piwinski, J. J.; Xiao, D.; Chen, X. WO-2001044200, 2001; Chem. Abstr. 2001, 135, 61331. (h) Kuang, R.; Epp, J. B.; Ruan, S.; Chong, L. S.; Venkataraman, R.; Tu, J.; He, S.; Truong, T. M.; Groutas, W. C. Bioorg. Med. Chem. 2000, 8, 1005-1016. (i) He, S.; Kuang, R.; Venkataraman, R.; Tu, J.; Truong, T. M.; Chan, H.-K.; Groutas, W. C. Bioorg. Med. Chem. 2000, 8, 1713-11717. (j) Martinez, A.; Gil, C.; Perez, C.; Castro, A.; Prieto, C.; Otero, J.; Andrei, G.; Snoeck, R.; Balazarini, J.; De Clerk, E. J. Med. Chem. 2000, 43, 3267-3273. (k) Benson, G. M.; Rutledge, M. C.; Widdowson, K. L. WO-2000076501, 2000; Chem. Abstr. 2001, 134, 56675. (l) Lee, C. H.; Kohn, H. J. Pharm. Sci. 1990, 79, 716-718.
7. For selected examples from recent literature, see: (a) Zhong, J.; Gan, X. Bioorg. Med. Chem. 2004, 12, 589-593. (b) Collins, I. J.; Cooper, L. C. WO-2003093264, 2003; Chem. Abstr. 2003, 139, 381492. (c) Kadow, J. F.; Regueiro-Ren, A.; Xue, Q. M. WO-2004000210, 2003; Chem. Abstr. 2003, 140, 59662. (d) Cherney, R. J.; King, B. W. WO-2002028846, 2002; Chem. Abstr. 2002, 136, 309923. (e) Schaal, W.; Karlsson, A.; Ahlsén, G.; Lindberg, J.; Andersson, H. O.; Danielson, U. H.; Classon, B.; Unge, T.; Samuelsson, B.; Hultén, J.; Hallberg, A.; Karlén, A. J. Med. Chem. 2001, 44, 155-169. (f) Groutas, W. C.; He, S.; Kuang, R.; Ruan, S.; Tu, J.; Chan, H.-K. Bioorg. Med. Chem. 2001, 9, 1543-1548. (g) Shih, N.-Y.; Shue, H.-J.; Reichard, G. A.; Paliwal, S.; Blynthin, D. J.; Piwinski, J. J.; Xiao, D.; Chen, X. WO-2001044200, 2001; Chem. Abstr. 2001, 135, 61331. (h) Kuang, R.; Epp, J. B.; Ruan, S.; Chong, L. S.; Venkataraman, R.; Tu, J.; He, S.; Truong, T. M.; Groutas, W. C. Bioorg. Med. Chem. 2000, 8, 1005-1016. (i) He, S.; Kuang, R.; Venkataraman, R.; Tu, J.; Truong, T. M.; Chan, H.-K.; Groutas, W. C. Bioorg. Med. Chem. 2000, 8, 1713-11717. (j) Martinez, A.; Gil, C.; Perez, C.; Castro, A.; Prieto, C.; Otero, J.; Andrei, G.; Snoeck, R.; Balazarini, J.; De Clerk, E. J. Med. Chem. 2000, 43, 3267-3273. (k) Benson, G. M.; Rutledge, M. C.; Widdowson, K. L. WO-2000076501, 2000; Chem. Abstr. 2001, 134, 56675. (l) Lee, C. H.; Kohn, H. J. Pharm. Sci. 1990, 79, 716-718.
8. For selected examples from recent literature, see: (a) Zhong, J.; Gan, X. Bioorg. Med. Chem. 2004, 12, 589-593. (b) Collins, I. J.; Cooper, L. C. WO-2003093264, 2003; Chem. Abstr. 2003, 139, 381492. (c) Kadow, J. F.; Regueiro-Ren, A.; Xue, Q. M. WO-2004000210, 2003; Chem. Abstr. 2003, 140, 59662. (d) Cherney, R. J.; King, B. W. WO-2002028846, 2002; Chem. Abstr. 2002, 136, 309923. (e) Schaal, W.; Karlsson, A.; Ahlsén, G.; Lindberg, J.; Andersson, H. O.; Danielson, U. H.; Classon, B.; Unge, T.; Samuelsson, B.; Hultén, J.; Hallberg, A.; Karlén, A. J. Med. Chem. 2001, 44, 155-169. (f) Groutas, W. C.; He, S.; Kuang, R.; Ruan, S.; Tu, J.; Chan, H.-K. Bioorg. Med. Chem. 2001, 9, 1543-1548. (g) Shih, N.-Y.; Shue, H.-J.; Reichard, G. A.; Paliwal, S.; Blynthin, D. J.; Piwinski, J. J.; Xiao, D.; Chen, X. WO-2001044200, 2001; Chem. Abstr. 2001, 135, 61331. (h) Kuang, R.; Epp, J. B.; Ruan, S.; Chong, L. S.; Venkataraman, R.; Tu, J.; He, S.; Truong, T. M.; Groutas, W. C. Bioorg. Med. Chem. 2000, 8, 1005-1016. (i) He, S.; Kuang, R.; Venkataraman, R.; Tu, J.; Truong, T. M.; Chan, H.-K.; Groutas, W. C. Bioorg. Med. Chem. 2000, 8, 1713-11717. (j) Martinez, A.; Gil, C.; Perez, C.; Castro, A.; Prieto, C.; Otero, J.; Andrei, G.; Snoeck, R.; Balazarini, J.; De Clerk, E. J. Med. Chem. 2000, 43, 3267-3273. (k) Benson, G. M.; Rutledge, M. C.; Widdowson, K. L. WO-2000076501, 2000; Chem. Abstr. 2001, 134, 56675. (l) Lee, C. H.; Kohn, H. J. Pharm. Sci. 1990, 79, 716-718.
9. For selected examples from recent literature, see: (a) Zhong, J.; Gan, X. Bioorg. Med. Chem. 2004, 12, 589-593. (b) Collins, I. J.; Cooper, L. C. WO-2003093264, 2003; Chem. Abstr. 2003, 139, 381492. (c) Kadow, J. F.; Regueiro-Ren, A.; Xue, Q. M. WO-2004000210, 2003; Chem. Abstr. 2003, 140, 59662. (d) Cherney, R. J.; King, B. W. WO-2002028846, 2002; Chem. Abstr. 2002, 136, 309923. (e) Schaal, W.; Karlsson, A.; Ahlsén, G.; Lindberg, J.; Andersson, H. O.; Danielson, U. H.; Classon, B.; Unge, T.; Samuelsson, B.; Hultén, J.; Hallberg, A.; Karlén, A. J. Med. Chem. 2001, 44, 155-169. (f) Groutas, W. C.; He, S.; Kuang, R.; Ruan, S.; Tu, J.; Chan, H.-K. Bioorg. Med. Chem. 2001, 9, 1543-1548. (g) Shih, N.-Y.; Shue, H.-J.; Reichard, G. A.; Paliwal, S.; Blynthin, D. J.; Piwinski, J. J.; Xiao, D.; Chen, X. WO-2001044200, 2001; Chem. Abstr. 2001, 135, 61331. (h) Kuang, R.; Epp, J. B.; Ruan, S.; Chong, L. S.; Venkataraman, R.; Tu, J.; He, S.; Truong, T. M.; Groutas, W. C. Bioorg. Med. Chem. 2000, 8, 1005-1016. (i) He, S.; Kuang, R.; Venkataraman, R.; Tu, J.; Truong, T. M.; Chan, H.-K.; Groutas, W. C. Bioorg. Med. Chem. 2000, 8, 1713-11717. (j) Martinez, A.; Gil, C.; Perez, C.; Castro, A.; Prieto, C.; Otero, J.; Andrei, G.; Snoeck, R.; Balazarini, J.; De Clerk, E. J. Med. Chem. 2000, 43, 3267-3273. (k) Benson, G. M.; Rutledge, M. C.; Widdowson, K. L. WO-2000076501, 2000; Chem. Abstr. 2001, 134, 56675. (l) Lee, C. H.; Kohn, H. J. Pharm. Sci. 1990, 79, 716-718.
10. For selected examples from recent literature, see: (a) Zhong, J.; Gan, X. Bioorg. Med. Chem. 2004, 12, 589-593. (b) Collins, I. J.; Cooper, L. C. WO-2003093264, 2003; Chem. Abstr. 2003, 139, 381492. (c) Kadow, J. F.; Regueiro-Ren, A.; Xue, Q. M. WO-2004000210, 2003; Chem. Abstr. 2003, 140, 59662. (d) Cherney, R. J.; King, B. W. WO-2002028846, 2002; Chem. Abstr. 2002, 136, 309923. (e) Schaal, W.; Karlsson, A.; Ahlsén, G.; Lindberg, J.; Andersson, H. O.; Danielson, U. H.; Classon, B.; Unge, T.; Samuelsson, B.; Hultén, J.; Hallberg, A.; Karlén, A. J. Med. Chem. 2001, 44, 155-169. (f) Groutas, W. C.; He, S.; Kuang, R.; Ruan, S.; Tu, J.; Chan, H.-K. Bioorg. Med. Chem. 2001, 9, 1543-1548. (g) Shih, N.-Y.; Shue, H.-J.; Reichard, G. A.; Paliwal, S.; Blynthin, D. J.; Piwinski, J. J.; Xiao, D.; Chen, X. WO-2001044200, 2001; Chem. Abstr. 2001, 135, 61331. (h) Kuang, R.; Epp, J. B.; Ruan, S.; Chong, L. S.; Venkataraman, R.; Tu, J.; He, S.; Truong, T. M.; Groutas, W. C. Bioorg. Med. Chem. 2000, 8, 1005-1016. (i) He, S.; Kuang, R.; Venkataraman, R.; Tu, J.; Truong, T. M.; Chan, H.-K.; Groutas, W. C. Bioorg. Med. Chem. 2000, 8, 1713-11717. (j) Martinez, A.; Gil, C.; Perez, C.; Castro, A.; Prieto, C.; Otero, J.; Andrei, G.; Snoeck, R.; Balazarini, J.; De Clerk, E. J. Med. Chem. 2000, 43, 3267-3273. (k) Benson, G. M.; Rutledge, M. C.; Widdowson, K. L. WO-2000076501, 2000; Chem. Abstr. 2001, 134, 56675. (l) Lee, C. H.; Kohn, H. J. Pharm. Sci. 1990, 79, 716-718.
11. For selected examples from recent literature, see: (a) Zhong, J.; Gan, X. Bioorg. Med. Chem. 2004, 12, 589-593. (b) Collins, I. J.; Cooper, L. C. WO-2003093264, 2003; Chem. Abstr. 2003, 139, 381492. (c) Kadow, J. F.; Regueiro-Ren, A.; Xue, Q. M. WO-2004000210, 2003; Chem. Abstr. 2003, 140, 59662. (d) Cherney, R. J.; King, B. W. WO-2002028846, 2002; Chem. Abstr. 2002, 136, 309923. (e) Schaal, W.; Karlsson, A.; Ahlsén, G.; Lindberg, J.; Andersson, H. O.; Danielson, U. H.; Classon, B.; Unge, T.; Samuelsson, B.; Hultén, J.; Hallberg, A.; Karlén, A. J. Med. Chem. 2001, 44, 155-169. (f) Groutas, W. C.; He, S.; Kuang, R.; Ruan, S.; Tu, J.; Chan, H.-K. Bioorg. Med. Chem. 2001, 9, 1543-1548. (g) Shih, N.-Y.; Shue, H.-J.; Reichard, G. A.; Paliwal, S.; Blynthin, D. J.; Piwinski, J. J.; Xiao, D.; Chen, X. WO-2001044200, 2001; Chem. Abstr. 2001, 135, 61331. (h) Kuang, R.; Epp, J. B.; Ruan, S.; Chong, L. S.; Venkataraman, R.; Tu, J.; He, S.; Truong, T. M.; Groutas, W. C. Bioorg. Med. Chem. 2000, 8, 1005-1016. (i) He, S.; Kuang, R.; Venkataraman, R.; Tu, J.; Truong, T. M.; Chan, H.-K.; Groutas, W. C. Bioorg. Med. Chem. 2000, 8, 1713-11717. (j) Martinez, A.; Gil, C.; Perez, C.; Castro, A.; Prieto, C.; Otero, J.; Andrei, G.; Snoeck, R.; Balazarini, J.; De Clerk, E. J. Med. Chem. 2000, 43, 3267-3273. (k) Benson, G. M.; Rutledge, M. C.; Widdowson, K. L. WO-2000076501, 2000; Chem. Abstr. 2001, 134, 56675. (l) Lee, C. H.; Kohn, H. J. Pharm. Sci. 1990, 79, 716-718.
12. For selected examples from recent literature, see: (a) Zhong, J.; Gan, X. Bioorg. Med. Chem. 2004, 12, 589-593. (b) Collins, I. J.; Cooper, L. C. WO-2003093264, 2003; Chem. Abstr. 2003, 139, 381492. (c) Kadow, J. F.; Regueiro-Ren, A.; Xue, Q. M. WO-2004000210, 2003; Chem. Abstr. 2003, 140, 59662. (d) Cherney, R. J.; King, B. W. WO-2002028846, 2002; Chem. Abstr. 2002, 136, 309923. (e) Schaal, W.; Karlsson, A.; Ahlsén, G.; Lindberg, J.; Andersson, H. O.; Danielson, U. H.; Classon, B.; Unge, T.; Samuelsson, B.; Hultén, J.; Hallberg, A.; Karlén, A. J. Med. Chem. 2001, 44, 155-169. (f) Groutas, W. C.; He, S.; Kuang, R.; Ruan, S.; Tu, J.; Chan, H.-K. Bioorg. Med. Chem. 2001, 9, 1543-1548. (g) Shih, N.-Y.; Shue, H.-J.; Reichard, G. A.; Paliwal, S.; Blynthin, D. J.; Piwinski, J. J.; Xiao, D.; Chen, X. WO-2001044200, 2001; Chem. Abstr. 2001, 135, 61331. (h) Kuang, R.; Epp, J. B.; Ruan, S.; Chong, L. S.; Venkataraman, R.; Tu, J.; He, S.; Truong, T. M.; Groutas, W. C. Bioorg. Med. Chem. 2000, 8, 1005-1016. (i) He, S.; Kuang, R.; Venkataraman, R.; Tu, J.; Truong, T. M.; Chan, H.-K.; Groutas, W. C. Bioorg. Med. Chem. 2000, 8, 1713-11717. (j) Martinez, A.; Gil, C.; Perez, C.; Castro, A.; Prieto, C.; Otero, J.; Andrei, G.; Snoeck, R.; Balazarini, J.; De Clerk, E. J. Med. Chem. 2000, 43, 3267-3273. (k) Benson, G. M.; Rutledge, M. C.; Widdowson, K. L. WO-2000076501, 2000; Chem. Abstr. 2001, 134, 56675. (l) Lee, C. H.; Kohn, H. J. Pharm. Sci. 1990, 79, 716-718.
13. Bolli, M.; Boss, C.; Fischli, W.; Clozel, M.; Weller, T. WO-2002053557, 2002; Chem. Abstr. 2002, 137, 93766.
14. (a) The Practice of Medicinal Chemistry, 2nd ed; Wermuth, C. G., Ed.; Academic Press: London, 2003.
15. (b) Albright, J. D.; DeVries, V. G.; Du, M. T.; Largis, E. E.; Miner, T. G.; Reich, M. F.; Shepherd, R. G. J. Med. Chem. 1983, 26, 1393-1411.
16. Levchenko, E. S.; Budnik, L. V. J. Org. Chem. USSR (Engl. Transl.) 1975, 11, 2077-2082.
17. (a) Esteve, C.; Vidal, B. Tetrahedron Lett. 2002, 43, 1019-1021.
18. (b) Hogberg, M.; Engelhart, P.; Vrang, L.; Zhang, H. Bioorg. Med. Chem. Lett. 2000, 10, 265-268.
19. (c) Goya, P.; Lissavetzky, J.; Rozas, I. Synthesis 1989, 280-282.
20. (d) Wheeler, W. K.; Degering, F. J. Am. Chem. Soc. 1944, 66, 1242-1243 and references cited herein.
21. For a recent review on copper-catalyzed C-N bond formation, see: Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400-5449.
22. For recent reviews on palladium-catalyzed C-N bond formation, see: (a) Muci, A. B.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131. (b) Hartwig, J. F. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley-Interscience: New York, 2002; p 1051.
23. For recent reviews on palladium-catalyzed C-N bond formation, see: (a) Muci, A. B.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131. (b) Hartwig, J. F. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley-Interscience: New York, 2002; p 1051.
24. (a) Huang, X.; Anderson, K. W.; Zim, D.; Jiang, L.; Klapars, A.; Buchwald, S. L. J. Am. Chein. Soc. 2003, 125, 6653-6655.
25. (b) Strieter, E. R.; Blackmond, D. G.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 13978-13980.
26. (a) Yin, J.; Buchwald, S. L. Org. Lett. 2000, 2, 1101-1104.
27. (b) Yin, J.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 6043-6048.
28. He, H.; Wu, Y.-J. Tetrahedron Lett. 2003, 44, 3385-3386.
29. Burton, G.; Cao, P.; Gang, L.; Rivero, R. Org. Lett 2003, 5, 4373-4376.
30. (a) McManus, J. M.; McFarland, J. W.; Gerber, C. F.; McLamore, W. M.; Laubach G. D. J. Med. Chem. 1965, 8, 766-776.
31. (b) Aeberli, P.; Gogerty, J.; Houlihan, W. J. J. Med. Chem. 1967, 10, 636-642.
32. (a) Abdaoui, M.; Dewynter, G.; Aouf, N.; Favre, G.; Morere, A.; Montero, J.-L. Bioorg. Med. Chem. 1996, 4, 1227-1235.
33. (b) Kavalek, J.; Kralikova, U.; Machacek, V.; Sedlak, M.; Sterba, V. Collect. Czech. Chem. Commun. 1990, 55, 203-222.
34. Winum, J.-Y.; Toupet, L.; Barragan, V.; Dewynter, G.; Montero, J.-L. Org. Lett. 2001, 3, 2241-2243.
35. 2 for 30 s and charged with anhydrous dioxane (2.5 mL). The flask was heated at 80°C for 18 h under a nitrogen atmosphere. The reaction mixture was then allowed to cool to room temperature and diluted with dichloromethane (5 mL), and acetic acid was added (500 μL). After filtration through a cotton wool plug, the crude mixture was concentrated under vacuum and purified by reverse-phase HPLC to afford the product 5 in 74% yield.
36. This is consistent with previous reports of the limited functional group compatibility of KOt-Bu when used as a stoichiometric base in a palladium coupling reaction: Wolfe, J. P.; Buchwald, S. L. Tetrahedron Lett. 1997, 38, 6359-6362.
37. During the course of our work with N,N-disubstituted sulfamides, we have observed that they can undergo base-catalyzed thermal decomposition to release the corresponding amine. This has previously been reported in the literature: Kavalek, J.; Kralikova, U.; Machacek, V.; Seldlak, M.; Sterba, V. Collec. Czech. Chem. Commun. 1990, 55, 202-222. We thus suspect that 8 is the result of a palladium-catalyzed coupling between morpholine and bromobenzene.