Synthesis of 1H-indol-2-yl-(4-aryl)-quinolin-2(1H)-ones via Pd-catalyzed regioselective cross-coupling reaction and cyclization

Schreiber, 2000, Science, 287, 1964, 10.1126/science.287.5460.1964 Schreiber, 2003, Chem. Eng. News, 81, 51, 10.1021/cen-v081n009.p051 Yancopoulos, 2000, Nature, 407, 242, 10.1038/35025215 Carmeliet, 2000, Nature, 407, 249, 10.1038/35025220 Fang, 2007, J. Org. Chem., 72, 1341, 10.1021/jo062228w Palimkar, 2007, Tetrahedron, 63, 12786, 10.1016/j.tet.2007.09.075 Kuethe, 2005, J. Org. Chem., 70, 2555, 10.1021/jo0480545 Payack, 2005, J. Org. Chem., 70, 175, 10.1021/jo048334k Wong, 2004, J. Org. Chem., 69, 7761, 10.1021/jo048843m Davies, I. W.; Smitrovich, J. H.; Qu, C. (Merck & Co., Inc., U.S.A.). PCT Int. Appl. WO 2005000804, 2005; Karki, S. B.; Deshpande, S. R.; Thompson, K. C.; Payne, A. H.; Gandek, T. P. (Merck & Co. Inc. U.S.A.). PCT Int. Appl. WO 2004087651, 2004; Kuethe, 2003, Org. Lett., 5, 3975, 10.1021/ol035541i Fraley, 2004, Bioorg. Med. Chem. Lett., 14, 351, 10.1016/j.bmcl.2003.11.007 Hewawasam, 2003, J. Med. Chem., 46, 2819, 10.1021/jm030005h Boy, 2004, Bioorg. Med. Chem. Lett., 14, 5089, 10.1016/j.bmcl.2004.07.080 Hewawasam, 2004, Bioorg. Med. Chem. Lett., 14, 4479, 10.1016/j.bmcl.2004.06.051 Hewawasam, P. WO Patent 00/34244, 2000. Hewawasam, 2002, Bioorg. Med. Chem. Lett., 12, 1779, 10.1016/S0960-894X(02)00240-8 Angibaud, 2004, Eur. J. Org. Chem., 479, 10.1002/ejoc.200300538 Andresen, 2004, Org. Process Res. Dev., 8, 643, 10.1021/op049935g Mederski, 1997, Bioorg. Med. Chem. Lett., 7, 1883, 10.1016/S0960-894X(97)00319-3 Cappelli, 2004, J. Med. Chem., 47, 2574, 10.1021/jm031100t Beier, 1994, Heterocycles, 39, 117, 10.3987/COM-93-S(B)5 Hino, 1980, Chem. Pharm. Bull., 28, 2618, 10.1248/cpb.28.2618 Hino, 1989, Chem. Pharm. Bull., 37, 110, 10.1248/cpb.37.110 Yang, 2002, J. Org. Chem., 67, 7429, 10.1021/jo026025t Kappe, 1988, J. Heterocycl. Chem., 25, 857, 10.1002/jhet.5570250330 Kappe, 1999, Farmaco, 54, 309, 10.1016/S0014-827X(99)00030-0 Ziegler, 1965, Monatsh. Chem., 96, 418, 10.1007/BF00909449 Ziegler, 1959, Monatsh. Chem., 90, 762, 10.1007/BF00902404 Junek, 1959, Monatsh. Chem., 90, 822, 10.1007/BF00905670 Roschger, 1990, Liebigs Ann. Chem., 821, 10.1002/jlac.1990199001153 For recent reviews, see: Miyaura, 2002, Top. Curr. Chem., 219, 11, 10.1007/3-540-45313-X_2 Suzuki, 1999, J. Organomet. Chem., 576, 137, 10.1016/S0022-328X(98)01055-9 Littke, 2002, Angew. Chem., Int. Ed., 31, 3176 For selected examples, see: Ma, 2001, J. Org. Chem., 66, 4525, 10.1021/jo001679s Kondo, 2001, J. Organomet. Chem., 622, 149, 10.1016/S0022-328X(00)00869-X Muller, 2001, Organometallics, 20, 4384, 10.1021/om010524n Xu, 1998, Tetrahedron Lett., 39, 5159, 10.1016/S0040-4039(98)00986-1 Yu, 1998, Tetrahedron Lett., 39, 9347, 10.1016/S0040-4039(98)02161-3 Mahanty, 1997, Tetrahedron, 53, 13397, 10.1016/S0040-4020(97)00852-1 Cacchi, 1994, J. Organomet. Chem., 475, 289, 10.1016/0022-328X(94)84034-2 Arcadi, 1989, Tetrahedron Lett., 30, 2581, 10.1016/S0040-4039(01)80456-1 Utimoto, 1981, Tetrahedron Lett., 22, 4277, 10.1016/S0040-4039(01)82932-4 Van Esseveldt, 2003, Org. Lett., 5, 1717, 10.1021/ol034360d Kozawa, 2002, Tetrahedron Lett., 43, 1499, 10.1016/S0040-4039(02)00043-6 Torres, 2002, Tetrahedron, 58, 4487, 10.1016/S0040-4020(02)00394-0 Sashida, 1999, Synthesis, 1145, 10.1055/s-1999-3522 Kobayashi, 1998, J. Heterocycl. Chem., 35, 1043, 10.1002/jhet.5570350504 McDonald, 1997, Tetrahedron Lett., 38, 7687, 10.1016/S0040-4039(97)10006-5 Khan, 1997, Synlett, 1435, 10.1055/s-1997-1049 Ohe, 1991, J. Org. Chem., 56, 2267, 10.1021/jo00006a062 NagaraJan, 1989, Indian J. Chem., Sect. B, 28, 67 Sakamoto, 1988, Chem. Pharm. Bull., 36, 1305, 10.1248/cpb.36.1305 Taylor, 1985, Tetrahedron Lett., 26, 5963, 10.1016/S0040-4039(00)98272-8 Roesch, 2002, J. Org. Chem., 67, 86, 10.1021/jo010579z Zhang, 2002, Tetrahedron Lett., 43, 1359, 10.1016/S0040-4039(02)00005-9 Melis, 2002, Eur. J. Org. Chem., 22, 3779, 10.1002/1099-0690(200211)2002:22<3779::AID-EJOC3779>3.0.CO;2-J Anastasia, 2002, Tetrahedron Lett., 43, 5673, 10.1016/S0040-4039(02)01128-0 Bellina, 2000, Tetrahedron, 56, 2533, 10.1016/S0040-4020(00)00125-3 Qing, 2000, Tetrahedron Lett., 41, 7727, 10.1016/S0040-4039(00)01333-2 Kundu, 1998, J. Chem. Soc., Perkin Trans. 1, 561, 10.1039/a705450e Liao, 1995, J. Org. Chem., 60, 3711, 10.1021/jo00117a023 Ogawa, 1995, Heterocycles, 41, 2587, 10.3987/COM-95-7228 Trost, 2002, J. Am. Chem. Soc., 124, 2528, 10.1021/ja011840w Bates, 2002, Org. Lett., 4, 4727, 10.1021/ol0272040 Cutchins, 2002, Org. Lett., 4, 749, 10.1021/ol017195f Aschwanden, 2000, Org. Lett., 2, 2331, 10.1021/ol006095r McDonald, 2000, J. Am. Chem. Soc., 122, 4304, 10.1021/ja994229u Peng, 2003, J. Am. Chem. Soc., 125, 15006, 10.1021/ja038627f Tang, 2006, J. Org. Chem., 71, 8489, 10.1021/jo0614644 Peng, 2005, Org. Lett., 7, 3299, 10.1021/ol051126+ Wu, 2005, Chem. Lett., 34, 550, 10.1246/cl.2005.550