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41649113513
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(b) Romagnoli, R.; Baraldi, P. G.; Sarkar, T.; Carrion, M. D.; Cara, C. L.; Cruz-Lopez, O.; Preti, D.; Tabrizi, M. A.; Tolomeo, M.; Grimaudo, S.; Cristina, A. D.; Zonta, N.; Balzarini, J.; Brancale, A.; Hsieh, H.-P.; Hamel, E. J. Med. Chem. 2008, 51, 1464.
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45749141743
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Chen, L.11
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2 was previously reported, see: (a) Queiroz, M.-J. R. P.; Abreu, A. S.; Castanheira, E. M. S.; Ferreira, P. M. T. Tetrahedron 2007, 63, 2215.
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2 was previously reported, see: (a) Queiroz, M.-J. R. P.; Abreu, A. S.; Castanheira, E. M. S.; Ferreira, P. M. T. Tetrahedron 2007, 63, 2215.
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(b) Abreu, A. S.; Ferreira, P. M. T.; Queiroz, M.-J. R. P.; Ferreira, I. C. F. R.; Calhelha, R. C.; Estevinho, L. M. Eur. J. Org. Chem. 2005, 2951.
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Estevinho, L.M.6
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Venanzi, M.5
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34
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27144450136
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Only a few examples of Pd-catalyzed C-H amination have been reported to date, see: a
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Only a few examples of Pd-catalyzed C-H amination have been reported to date, see: (a) Tsang, W. C. P.; Zheng, N.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 14560.
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Tsang, W.C.P.1
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Buchwald, S.L.3
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33746071928
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(b) Thu, H.-Y.; Yu, W.-Y.; Che, C.-M. J. Am. Chem. Soc. 2006, 128, 9048.
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J. Am. Chem. Soc
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Thu, H.-Y.1
Yu, W.-Y.2
Che, C.-M.3
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36
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34547227201
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We have already reported the synthesis of indazoles using a Pd-catalyzed intramolecular C-H amination process, see: Inamoto, K, Saito, T, Katsuno, M, Sakamoto, T, Hiroya, K. Org. Lett. 2007, 9, 2931
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We have already reported the synthesis of indazoles using a Pd-catalyzed intramolecular C-H amination process, see: Inamoto, K.; Saito, T.; Katsuno, M.; Sakamoto, T.; Hiroya, K. Org. Lett. 2007, 9, 2931.
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0347778733
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Lee, K. Y.; Lee, C. G.; Kim, J. N. Tetrahedron Lett. 2003, 44, 1231.
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Tetrahedron Lett
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Lee, K.Y.1
Lee, C.G.2
Kim, J.N.3
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38
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58149379361
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Use of solvents such as DMF, NMP, MeCN, dioxane, toluene, and DCE resulted in decreased yields
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Use of solvents such as DMF, NMP, MeCN, dioxane, toluene, and DCE resulted in decreased yields.
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39
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58149383603
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We also examined the effect of a variety of additives such as phosphines, N-heterocyclic carbenes, tetraalkylammonium salts, inorganic bases, lithium and silver salts, and so on, all of which led to unsatisfactory results
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We also examined the effect of a variety of additives such as phosphines, N-heterocyclic carbenes, tetraalkylammonium salts, inorganic bases, lithium and silver salts, and so on, all of which led to unsatisfactory results.
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40
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58149395999
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Typical Procedure for the Pd-Catafyzed C-H Amination of Enamines (Table 1, entry 9) A mixture of 1 (50.0 mg, 0.14 mmol, Pd(OAc) 2 (3.2 mg, 0.014 mmol, and Cu(OAc)2 (26.0 mg, 0.14 mmol) in DMSO (2.9 mL) was stirred at 80°C for 24 h. The reaction mixture was extracted with EtOAc (3 x 5 mL) and the combined organic layer was washed with brine (10 mL, and dried over MgSO4. The solvent was evaporated and the residue was purified by silica gel column chromatography (hexane-EtOAc, 9:1) to give indole 2 (26.2 mg, 53, as a colorless solid. 1-(4- Methylphenylsulfonyl)-3-phenylindole (2) Mp 151-152°C (colorless needles from hexane-EtOAc, IR (film, 2924, 1597, 1447, 1371, 1175, 669 cm -1. 1H NMR (400 MHz, CDCl3, δ, 2.34 (3 H, s, 7.22 (2 H, d, J, 8.2 Hz, 7.26-7.30 (1 H, m, 7.34-7.38 (2 H, m, 7.46 (2 H, t, J, 7.8 Hz, 7.59-7.61 (2 H, m, 7.69 (1 H, s, 7.77 1 H, d, J
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2S: C, 72.60; H, 4.93; N, 4.03. Found C, 72.63; H, 5.08; N, 3.99.
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41
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58149391119
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Typical Procedure for the Synthesis of Enol Ether (4a, Table 2, entry 1) To a solution of(methoxymethyl)triphenylphosphinium chloride (1.1 g, 3.1 mmol) in anhyd dioxane (5 mL) was slowly added BuLi (1.53 M solution in hexane, 2.3 mL, 3.1 mmol) at 0°C and stirred for 30 min at the same temperature. A solution of 3a (0.50 g, 2.1 mmol) in anhyd dioxane (10 mL) was then slowly added at 0°C, and the mixture was heated under reflux for 10 h. The reaction mixture was treated with sat. aq NH4Cl soin (5 mL, and the aqueous phase was extracted with EtOAc (3 x 10 mL, The combined organic layer was washed with brine (5 mL) and dried over MgSO4. The solvent was evaporated, and the residue was purified by silica gel column chromatography (hexane-EtOAc, 9:1) to give 4a (0.4 g, 67, as a colorless oil. 1,1-Bis(4-methoxyphenyl)-2-methoxyethene (4a) IR (film, 2359, 1341, 1508, 1244 cm-1. 1H NMR 400 MHZ, CDCl3
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3): δ = 2.44 (3 H, s), 3.77 (3 H, s), 3.82 (3 H, s), 6.22 (1 H, d, J = 11.4 Hz), 6.65 (1 H, d, J = 11.4 Hz)
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42
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58149396026
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Geometry of enamine 5f was determined by NOESY.
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Geometry of enamine 5f was determined by NOESY.
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43
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58149392319
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1H NMR spectroscopy.
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1H NMR spectroscopy.
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