Query Query
1. Query N
Results
Date
12 reactions in Reaxys
2018-03-18 19h:26m:12s (EST)
Search as: As drawn
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NH
Br N
Rx-ID: 4147685 View in Reaxys 1/12 Yield
Conditions & References
87 %
Stage 1: With potassium hydroxide in N,N-dimethyl-formamide, Time= 1h Stage 2: in N,N-dimethyl-formamide, T= 50 °C , Further stages. Qi, Ting; Qiu, Wenfeng; Liu, Yunqi; Zhang, Hengjun; Gao, Xike; Liu, Ying; Lu, Kun; Du, Chunyan; Yu, Gui; Zhu, Daoben; Journal of Organic Chemistry; vol. 73; nb. 12; (2008); p. 4638 - 4643 View in Reaxys
55 %
With 18-crown-6 ether, sodium hydride in tetrahydrofuran, Time= 3h Abel, Ernesto; Fedders, Megan F.; Gokel, George W.; Journal of the American Chemical Society; vol. 117; nb. 4; (1995); p. 1265 - 1270 View in Reaxys Alkylation Abel, Ernesto; De Wall, Stephen L.; Edwards, W. Barry; Lalitha; Covey, Douglas F.; Gokel, George W.; Journal of Organic Chemistry; vol. 65; nb. 19; (2000); p. 5901 - 5909 View in Reaxys 11.1 :To a solution of 1 H-indole in DMSO was added KOH at RT and was stirred for 30 minutes. Then to this mixture, 1-bromo-hexane was added and stirred for 3 hours. The reaction was treated with saturated ammonium chloride and ethyl acetate. The product was purified by column chromatography. Stage 1: With potassium hydoxide in dimethyl sulfoxide, Time= 0.5h, T= 20 °C Stage 2: in dimethyl sulfoxide, Time= 3h Patent; THE ROYAL INSTITUTION FOR THE ADVANCEMENT OF LEARNING/MCGILL UNIVERSITY; FLORIDA INSTITUTE OF TECHNOLOGY; POWELL, William S.; ROKACH, Joshua; WO2010/127452; (2010); (A1) English View in Reaxys General procedure for the preparation of indole derivatives (4d‑4g) General procedure: Indoles (1 mmol), potassium carbonate (1.3 mmol), and the corresponding alkyl halide (1.1 mmol) were dissolved in DMF (5 ml) and heated under reflux at 100 °C. Upon completion of the reaction (monitored by TLC), the crude product was poured in iced water. The obtained solids were dissolved in ethyl acetate to give the crystal of pure products. With potassium carbonate in N,N-dimethyl-formamide, Time= 24h, T= 100 °C Mohammadi Ziarani; Hajiabbasi; Badiei; Journal of the Iranian Chemical Society; vol. 12; nb. 9; (2015); p. 1649 1654 View in Reaxys
N
I
N
Rx-ID: 34138626 View in Reaxys 2/12 Yield 85 %
Conditions & References With tributyl-amine, fac-tris[2-phenylpyridinato-C2,N]iridium(III), diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate in acetonitrile, Time= 16h, T= 25 - 30 °C , Inert atmosphere, Irradiation Nguyen, John D.; D'Amato, Erica M.; Narayanam, Jagan M. R.; Stephenson, Corey R. J.; Nature Chemistry; vol. 4; nb. 10; (2012); p. 854 - 859
Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
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View in Reaxys
NH
OH
N
Rx-ID: 29455239 View in Reaxys 3/12 Yield
Conditions & References
82 %
With Shvo's catalyst, toluene-4-sulfonic acid in toluene, Time= 24h, T= 110 °C , Inert atmosphere Baehn, Sebastian; Imm, Sebastian; Mevius, Kathleen; Neubert, Lorenz; Tillack, Annegret; Williams, Jonathan M. J.; Beller, Matthias; Chemistry - A European Journal; vol. 16; nb. 12; (2010); p. 3590 - 3593 View in Reaxys
O S N
O N
Rx-ID: 30459142 View in Reaxys 4/12 Yield
Conditions & References
96 %
With Raney nickel in ethanol, Time= 5h, Reflux Karchava; Shuleva; Ovcharenko; Yurovskaya; Chemistry of Heterocyclic Compounds; vol. 46; nb. 3; (2010); p. 291 - 301 View in Reaxys
O
S
O
N
N
Rx-ID: 30459143 View in Reaxys 5/12 Yield
Conditions & References
93 %
With Raney nickel in ethanol, Time= 5h, Reflux Karchava; Shuleva; Ovcharenko; Yurovskaya; Chemistry of Heterocyclic Compounds; vol. 46; nb. 3; (2010); p. 291 - 301 View in Reaxys
O S NH
OH
N
O
Rx-ID: 30459156 View in Reaxys 6/12 Yield
Conditions & References Reaction Steps: 2
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1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran; ethanol / 0 - 25 °C / Inert atmosphere 2: Raney nickel / ethanol / 5 h / Reflux With di-isopropyl azodicarboxylate, triphenylphosphine in tetrahydrofuran, ethanol, 1: Mitsunobu reaction Karchava; Shuleva; Ovcharenko; Yurovskaya; Chemistry of Heterocyclic Compounds; vol. 46; nb. 3; (2010); p. 291 - 301 View in Reaxys
NH
N
S
Rx-ID: 30459164 View in Reaxys 7/12 Yield
Conditions & References Reaction Steps: 3 1: 3-chloro-benzenecarboperoxoic acid 2: azodicarboxylic acid dipiperidide; tributylphosphine / tetrahydrofuran; ethanol / 0 - 48 °C / Inert atmosphere 3: Raney nickel / ethanol / 5 h / Reflux With tributylphosphine, azodicarboxylic acid dipiperidide, 3-chloro-benzenecarboperoxoic acid in tetrahydrofuran, ethanol, 2: Mitsunobu reaction Karchava; Shuleva; Ovcharenko; Yurovskaya; Chemistry of Heterocyclic Compounds; vol. 46; nb. 3; (2010); p. 291 - 301 View in Reaxys
NH
O
N
S O
Rx-ID: 30459181 View in Reaxys 8/12 Yield
Conditions & References Reaction Steps: 2 1: azodicarboxylic acid dipiperidide; tributylphosphine / tetrahydrofuran; ethanol / 0 - 48 °C / Inert atmosphere 2: Raney nickel / ethanol / 5 h / Reflux With tributylphosphine, azodicarboxylic acid dipiperidide in tetrahydrofuran, ethanol, 1: Mitsunobu reaction Karchava; Shuleva; Ovcharenko; Yurovskaya; Chemistry of Heterocyclic Compounds; vol. 46; nb. 3; (2010); p. 291 - 301 View in Reaxys
NH S N
Rx-ID: 30459198 View in Reaxys 9/12 Yield
Conditions & References Reaction Steps: 3 1: oxone / methanol; water / 0 - 20 °C 2: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran; ethanol / 0 - 25 °C / Inert atmosphere 3: Raney nickel / ethanol / 5 h / Reflux With oxone, di-isopropyl azodicarboxylate, triphenylphosphine in tetrahydrofuran, methanol, ethanol, water, 2: Mitsunobu reaction
Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
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Karchava; Shuleva; Ovcharenko; Yurovskaya; Chemistry of Heterocyclic Compounds; vol. 46; nb. 3; (2010); p. 291 - 301 View in Reaxys
Br Z
NH 2 Br
N
Rx-ID: 28876030 View in Reaxys 10/12 Yield 21 %
Conditions & References With copper(l) iodide, potassium carbonate, N,N`-dimethylethylenediamine in toluene, Time= 24h, T= 110 °C , Inert atmosphere Hodgkinson, Roy C.; Schulz, Jurgen; Willis, Michael C.; Organic and Biomolecular Chemistry; vol. 7; nb. 3; (2009); p. 432 - 434 View in Reaxys
N
Rx-ID: 6420534 View in Reaxys 11/12 Yield
Conditions & References Indol, n-Hexylbromid, KOH/DMSO Patent; Ciba-Geigy AG; CH556839; (1974); DE2257710; ; vol. 79; nb. 67821 View in Reaxys ... falling within the ambit of the formula 1-R8 -pyrrole and carbazole compounds falling within the ambit of the formula 9-R8 -carbazole which are useful in the practice of the processes of this invention for producing the aforesaid methanes and alkanes of Formulas I, XI and XVI. ... 1-Methyl-5-bromo-6-nitroindole, 2,5,6-Trimethylindole, 1-Isobutyl-2-methylindole, 6-Bromo-2-methylindole, 1-Hexylindole, 1-(2,5-Dimethylbenzyl)-2-methylindole, 2-Propylindole, 6-Chloro-2-phenylindole, ... Patent; Sterling Drug Inc.; US4257954; (1981); (A1) English View in Reaxys The following compounds are exemplary of indoles, pyrroles and carbazoles useful in the practice of this invention. ... 1-Isobutyl-2-methylindole, 6-Bromo-2-methylindole, 1-Hexylindole, 1-(2,5-Dimethylbenzyl)-2-methylindole, ... Patent; Sterling Drug Inc.; US4307018; (1981); (A1) English View in Reaxys The following compounds are exemplary of indoles, pyrroles and carbazoles useful in the practice of this invention.
Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
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... 1-Methyl-5-bromo-6-nitroindole, 2,5,6-Trimethylindole, 1-Isobutyl-2-methylindole, 6-Bromo-2-methylindole, 1-Hexylindole, 1-(2,5-Dimethylbenzyl)-2-methylindole, 2-Propylindole, 6-Chloro-2-phenylindole, ... Patent; Sterling Drug Inc.; US4322352; (1982); (A1) English View in Reaxys Patent; Sterling Drug Inc.; US4251446; (1981); (A1) English View in Reaxys The following compounds are exemplary of indoles useful in the practice of this invention. ... 2-Ethyl-1-methylindole, 1-Isopropylindole, 2-Isopropylindole, 1-Isobutyl-2-methylindole, 1-Hexylindole, 2-Propylindole, 1-Isoamylindole and 1-(2-Ethylhexyl)-2-methylindole. Patent; Sterling Drug Inc.; US4417059; (1983); (A1) English View in Reaxys The following compounds are exemplary of indoles useful in the practice of this invention. ... 1,2-Dimethyl-6-nitroindole, 1-(4-Chlorobenzyl)-2-methyl-5-nitroindole, 1-Methyl-5-bromo-6-nitroindole, 2,5,6-Trimethylindole, 1-Isobutyl-2-methylindole, 6-Bromo-2-methylindole, 1-Hexylindole, 1-(2,5-Dimethylbenzyl)-2-methylindole, 2-Propylindole, 6-Chloro-2-phenylindole, ... Patent; The Hilton-Davis Chemical Co.; US4451657; (1984); (A1) English View in Reaxys The following compounds are exemplary of indoles useful in the practice of this invention. ... 1-Methyl-5-bromo-6-nitroindole, 2,5,6-Trimethylindole, 1-Isobutyl-2-methylindole, 6-Bromo-2-methylindole, 1-Hexylindole, 1-(2,5-Dimethylbenzyl)-2-methylindole, 2-Propylindole, 6-Chloro-2-phenylindole, ... Patent; Sterling Drug Inc.; US4075224; (1978); (A1) English View in Reaxys
Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
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NH N
N
Rx-ID: 1559645 View in Reaxys 12/12 Yield
Conditions & References Multistep reaction Hegedus, Louis S.; Winton, Peter M.; Varaprath Sudarsanan; Journal of Organic Chemistry; vol. 46; nb. 11; (1981); p. 2215 - 2221 View in Reaxys
Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
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