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Benzimidazoles form the nucleus of many drugs, for example, see: (a) Skalitzky, D. J.; Marakovits, J. T.; Maegley, K. A.; Ekker, A.; Yu, X.-H.; Hostomsky, Z.; Webber, S. E.; Eastman, B. W.; Almassy, R.; Li, J.; Curtin, N. J.; Newell, D. R.; Calvert, A. H.; Griffin, R. J.; Golding, B. T. J. Med. Chem. 2003, 46, 210-213. (b) Valdez, J.; Cedillo, R.; Hernández-Campos, A.; Yépez, L.; Hernández-Luis, F.; Navarrete-Vázquez, G.; Tapia, A.; Cortés, R.; Hernández, M.; Castillo, R. Bioorg. Med. Chem. Lett. 2002, 12, 2221-2224. (c) Rao, A.; Chimirri, A.; De Clercq, E.; Monforte, A. M.; Monforte, P.; Pannecouque, C.; Zappalà, M. Il Farmaco 2002, 57, 819-823.
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25
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Benzimidazoles form the nucleus of many drugs, for example, see: (a) Skalitzky, D. J.; Marakovits, J. T.; Maegley, K. A.; Ekker, A.; Yu, X.-H.; Hostomsky, Z.; Webber, S. E.; Eastman, B. W.; Almassy, R.; Li, J.; Curtin, N. J.; Newell, D. R.; Calvert, A. H.; Griffin, R. J.; Golding, B. T. J. Med. Chem. 2003, 46, 210-213. (b) Valdez, J.; Cedillo, R.; Hernández-Campos, A.; Yépez, L.; Hernández-Luis, F.; Navarrete-Vázquez, G.; Tapia, A.; Cortés, R.; Hernández, M.; Castillo, R. Bioorg. Med. Chem. Lett. 2002, 12, 2221-2224. (c) Rao, A.; Chimirri, A.; De Clercq, E.; Monforte, A. M.; Monforte, P.; Pannecouque, C.; Zappalà, M. Il Farmaco 2002, 57, 819-823.
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Hartwig has carried out palladium-catalyzed intermolecular amination reactions using aqueous hydroxide as the base. However, these reactions were carried out in organic solvents with sufficient water only to dissolve the hydroxide, typically 1 equiv. See: Kuwano, R.; Utsunomiya, M.; Hartwig, J. F. J. Org. Chem. 2002, 67, 6479-6486.
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For examples of aqueous Suzuki reactions, see: (a) Sakurai, H.; Tsukuda, T.; Hirao, T. J. Org. Chem. 2002, 67, 2721-2722. (b) Badone, D.; Baroni, M.; Cardamone R.; Ielmini, A.; Guzzi, U. J. Org. Chem. 1997, 62, 7170-7173.
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34
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12444333847
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note
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A laboratory microwave instrument with a monomodal cavity and sealed reaction vessels was used: a Smith Creator available from Personal Chemistry AB, Uppsala, Sweden.
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35
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This is in contrast to observations by Hartwig, see: Hartwig, J. F. Synlett 1997, 329-340.
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Synlett
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Hartwig, J.F.1
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36
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note
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A control reaction in the absence of any palladium catalyst was carried out. After 167 min at 160 °C a 28% conversion was achieved.
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12444284014
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note
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Under these conditions, a thermal comparison was made with use of amidine 1. The reaction was carried out in a sealed microwave vial and was heated in an oil bath, preheated at 160 °C. The reaction mixture was heated for approximately the same time as the reaction carried out in the microwave (approximate due to longer heating and cooling periods). After this time a quantitative conversion to the benzimidazole had been achieved.
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Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G. ; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815-4195.
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Longbottom, D.A.6
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Scott, J.S.8
Storer, R.I.9
Taylor, S.J.10
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