Indexed keywords
AZAINDOLE;
AZAINDOLES;
FISCHER CYCLIZATIONS;
FUNCTIONALIZATION;
META-LATIONS;
PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS;
PYRROLOPYRIDINE;
CHLORINE;
CHLORINE COMPOUNDS;
CYCLIZATION;
LITHIUM;
LITHIUM COMPOUNDS;
NITROGEN COMPOUNDS;
PALLADIUM;
SYNTHESIS (CHEMICAL);
COMPLEXATION;
1 BROMO 3 CHLORO 9 METHYL 6,7,8,9 TETRAHYDRO 5H BETA CARBOLINE;
1,3 BIS(4 FLUOROPHENYL) 9 METHYL 6,7,8,9 TETRAHYDRO 5H BETA CARBOLINE;
1,3 DICHLORO 10 METHYL 5,6,7,8,9,10 HEXAHYDROCYCLOHEPTA[4,5]PYRROLO[2,3 C]PYRIDINE;
1,3 DICHLORO 5,6,7,8 TETRAHYDROCYCLOPENTA[4,5]PYRROLO[2,3 C]PYRIDINE;
1,3 DICHLORO 5,6,7,8,9,10 HEXAHYDROCYCLOHEPTA[4,5]PYRROLO[2,3 C]PYRIDINE;
1,3 DICHLORO 6,7,8,9 TETRAHYDRO 5H BETA CARBOLINE;
1,3 DICHLORO 9 METHYL 6,7,8,9 TETRAHYDRO 5H BETA CARBOLINE;
2 (3 CHLORO 10 METHYL 5,6,7,8,9,10 HEXAHYDROCYCLOHEPTA[4,5]PYRROLO[2,3 C]PYRIDIN 1 YL)PROPAN 2 OL;
2 (3 CHLORO 9 METHYL 6,7,8,9 TETRAHYDRO 5H BETA CARBOLIN 1 YL)PROPAN 2 OL;
2 PROPANOL;
3 (2 CHLORO 4 FLUOROPHENYL) 9 METHYL 6,7,8,9 TETRAHYDRO 5H BETA CARBOLINE;
3 (4 FLUOROPHENYL) 9 METHYL 6,7,8,9 TETRAHYDRO 5H BETA CARBOLINE;
3 CHLORO 1 (4 FLUOROPHENYL) 9 METHYL 6,7,8,9 TETRAHYDRO 5H BETA CARBOLINE;
3 CHLORO 1 DEUTERIO 9 METHYL 6,7,8,9 TETRAHYDRO 5H BETA CARBOLINE;
3 CHLORO 9 METHYL 6,7,8,9 TETRAHYDRO 5H BETA CARBOLINE;
3 CHLORO 9 METHYL 6,7,8,9 TETRAHYDRO 5H BETA CARBOLINE 1 CARBALDEHYDE;
5,7 DICHLORO 2,3 DIMETHYL 1 [[2 (TRIMETHYLSILYL)ETHOXY]METHYL] 1H PYRROLO[2,3 C]PYRIDINE;
5,7 DICHLORO 3 METHYL 2 PHENYL 1H PYRROLO[2,3 C]PYRIDINE;
5,7 DICHLOTO 2,3 DIMETHYL 1H PYRROLO[2,3 C]PYRIDINE;
9 METHYL 6,7,8,9 TETRAHYDRO 5H BETA CARBOLINE;
ACRYLIC ACID DERIVATIVE;
CARBOLINE DERIVATIVE;
CHLORINE;
ETHYL 3 (3 CHLORO 9 METHYL 6,7,8,9 TETRAHYDRO 5H BETA CARBOLIN 1 YL)ACRYLATE;
ETHYL 3 (5 CHLORO 2,3 DIMETHYL 1 [[2 (TRIMETHYLSILYL)ETHOXY]METHYL] 1H PYRROLO[2,3 C]PYRIDIN 7 YL)ACRYLATE;
ETHYL 3 [2 (3 CHLORO 9 METHYL 6,7,8,9 TETRAHYDRO 5H BETA CARBOLIN 1 YL) 5 FLUOROPHENYL]ACRYLATE;
INDOLE DERIVATIVE;
LITHIUM;
PYRIDINE DERIVATIVE;
TERT BUTYL 3 CHLORO 9 METHYL 6,7,8,9 TETRAHYDRO 5H BETA CARBOLINE 1 CARBOXYLATE;
UNCLASSIFIED DRUG;
ARTICLE;
CROSS COUPLING REACTION;
CYCLIZATION;
SYNTHESIS;
1
33847345910
For leading references to the physiological activity of indole derivatives, see: (a) Sturino, C. F.; O'Neill, G. P.; Lachance, N.; Boyd, M. J.; Berthelette, C.; Labelle, M.; Li, L. H.; Roy, B.; Scheigetz, J.; Tsou, N. N.; Bateman, K. P.; Day, S. H.; Levesque, J. F.; Seto, C.; Silva, J. M.; Carriere, M.; Denis, D.; Greig, G. M.; Kargman, S. L.; Lamontagne, S.; Mathieu, M.; Sawyer, N.; Slipetz, D. M.; Jones, T. R.; Mcauliffe, M.; Piechuta, H.; Nicoll-Griffith, D. A.; Wang, Z.; Zamboni, R. J.; Young, R. N.; Metters, K. M. J. Med. Chem. 2007, 50, 794.
For leading references to the physiological activity of indole derivatives, see: (a) Sturino, C. F.; O'Neill, G. P.; Lachance, N.; Boyd, M. J.; Berthelette, C.; Labelle, M.; Li, L. H.; Roy, B.; Scheigetz, J.; Tsou, N. N.; Bateman, K. P.; Day, S. H.; Levesque, J. F.; Seto, C.; Silva, J. M.; Carriere, M.; Denis, D.; Greig, G. M.; Kargman, S. L.; Lamontagne, S.; Mathieu, M.; Sawyer, N.; Slipetz, D. M.; Jones, T. R.; Mcauliffe, M.; Piechuta, H.; Nicoll-Griffith, D. A.; Wang, Z.; Zamboni, R. J.; Young, R. N.; Metters, K. M. J. Med. Chem. 2007, 50, 794.
2
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(b) Van Zandt, M. C.; Jones, M. L.; Gunn, D. E.; Geraci, L. S.; Jones, J. H.; Sawicki, D. R.; Sredy, J.; Jacot, J. L.; DiCioccio, A. T.; Petrova, T.; Mitschler, A.; Podjarny, A. D. J. Med. Chem. 2005, 48, 3141.
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Sredy, J.7
Jacot, J.L.8
DiCioccio, A.T.9
Petrova, T.10
Mitschler, A.11
Podjarny, A.D.12
3
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(c) Kuethe, J. T.; Wong, A.; Qu, C.; Smitrovich, J.; Davies, I. W.; Hughes, D. L. J. Org. Chem. 2005, 70, 2555.
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and references therein. For review on indoles synthesis, see
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and references therein. For recent reviews on palladium-catalyzed synthesis of indoles, see: a
For recent reviews on palladium-catalyzed synthesis of indoles, see: (a) Humphrey, G. R.; Kuethe, J. T. Chem. Rev. 2006, 106, 2875; and references therein.
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7
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For leading reference to the physiological activity of azaindole derivatives, see: a
For leading reference to the physiological activity of azaindole derivatives, see: (a) Kim, K. S.; Zhang, L.; Schmidt, R.; Cai, Z.-W.; Wei, D.; Williams, D. K.; Lombardo, L. J.; Trainor, G. L.; Xie, D.; Zhang, Y.; An, Y.; Sack, J. S.; Tokarski, J. S.; Darienzo, C.; Kamath, A.; Marathe, P.; Zhang, Y.; Lippy, J.; Jeyaseelan, R. Sr.; Wautlet, B.; Henley, B.; Gullo-Brown, J.; Manne, V.; Hunt, J. T.; Fargnoli, J.; Borzilleri, R. M. J. Med. Chem. 2008, 51, 5330.
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Kim, K.S.1
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Schmidt, R.3
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Lombardo, L.J.7
Trainor, G.L.8
Xie, D.9
Zhang, Y.10
An, Y.11
Sack, J.S.12
Tokarski, J.S.13
Darienzo, C.14
Kamath, A.15
Marathe, P.16
Zhang, Y.17
Lippy, J.18
Jeyaseelan Sr., R.19
Wautlet, B.20
Henley, B.21
Gullo-Brown, J.22
Manne, V.23
Hunt, J.T.24
Fargnoli, J.25
Borzilleri, R.M.26
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8
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(b) Lu, R.-J.; Tucker, J. A.; Zinevitch, T.; Kirichenko, O.; Konoplev, V.; Kuznetsova, S.; Sviridov, S.; Pickens, J.; Tandel, S.; Brahmachary, E.; Yang, Y.; Wang, J.; Freel, S.; Fisher, S.; Sullivan, A.; Zhou, J.; Stanfield-Oakley, S.; Greenberg, M.; Bolognesi, D.; Bray, B.; Koszalka, B.; Jeffs, P.; Khasanov, A.; Ma, Y.-A.; Jeffries, C.; Liu, C.; Proskurina, T.; Zhu, T.; Chucholowski, A.; Li, R.; Sexton, C. J. Med. Chem. 2007, 50, 6535.
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Pickens, J.8
Tandel, S.9
Brahmachary, E.10
Yang, Y.11
Wang, J.12
Freel, S.13
Fisher, S.14
Sullivan, A.15
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Stanfield-Oakley, S.17
Greenberg, M.18
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Bray, B.20
Koszalka, B.21
Jeffs, P.22
Khasanov, A.23
Ma, Y.-A.24
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Proskurina, T.27
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Chucholowski, A.29
Li, R.30
Sexton, C.31
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9
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(c) Cooper, L. C.; Chicchi, G. G.; Dinnell, K.; Elliott, J. M.; Hollingworth, G. J.; Kurtz, M. M.; Locker, K. L.; Morrison, D.; Shaw, D. E.; Tsao, K.- L.; Watt, A. P.; Williams, A. R.; Swain, C. J. Bioorg. Med. Chem. Lett. 2001, 11, 1233.
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Kurtz, M.M.6
Locker, K.L.7
Morrison, D.8
Shaw, D.E.9
Tsao, K.L.10
Watt, A.P.11
Williams, A.R.12
Swain, C.J.13
10
34547134215
For reviews on azaindoles synthesis, see: a
For reviews on azaindoles synthesis, see: (a) Popowycz, F.; Merour, J.-Y.; Joseph, B. Tetrahedron 2007, 63, 8689.
(2007)
Tetrahedron
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(b) Song, J. J.; Reeves, J. T.; Gallou, F.; Tan, Z.; Yee, N. K.; Senanayake, C. H. Chem. Soc. Rev. 2007, 36, 1120.
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12
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(c) Popowycz, F.; Routier, S.; Joseph, B.; Mérour, J.-Y. Tetrahedron 2007, 63, 1031.
(2007)
Tetrahedron
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Popowycz, F.1
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13
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(d) Le Hyaric, M.; Vieira de Almeida, M.; Nora de Souza, M. V. Quim. Nova 2002, 25, 1165.
(2002)
Quim. Nova
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16
27644544427
Roy, P. J.; Dufresne, C.; Lachance, N.; Leclerc, J.-P.; Boisvert, M.; Wang, Z.; Leblanc, Y. Synthesis 2005, 2751.
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Synthesis
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Roy, P.J.1
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Wang, Z.6
Leblanc, Y.7
18
33750598471
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Synthesis
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24
63449127916
The use of a condenser is not recommended
The use of a condenser is not recommended.
25
63449102820
Typically, aminopyridine 1 was isolated in less than 5
Typically, aminopyridine 1 was isolated in less than 5%.
27
0038644233
For selective lithium-bromine exchange on indoles, see: a
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34
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For leading references on ortho-lithiation of halogenated pyridines, see: a
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0035821359
and references therein. Review
(d) Review: Mongin, F.; Quéguiner, G. Tetrahedron 2001, 57, 4059; and references therein.
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Guram, A. S.; Wang, X.; Bunel, E. E.; Faul, M. M.; Larsen, R. D.; Martinelli, M. J. J. Org. Chem. 2007, 72, 5104.
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Martinelli, M.J.6
40
63449100545
1H NMR of the unpurified reaction mixture.
1H NMR of the unpurified reaction mixture.