Query Query
1. Query N
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Date
6 reactions in Reaxys
2018-03-03 04h:52m:44s (EST)
Search as: As drawn
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NH HO
N
Rx-ID: 46656675 View in Reaxys 1/6 Yield
Conditions & References
77 %
With chloro-(pentamethylcyclopentadienyl)-{5-methoxy-2-{1-[(4-methoxyphenyl)imino-N]ethyl}phenyl-C}-iridium(lll), potassium carbonate in 2,2,2-trifluoroethanol, Time= 12h, T= 100 °C Jiang, Xue; Tang, Weijun; Xue, Dong; Xiao, Jianliang; Wang, Chao; ACS Catalysis; vol. 7; nb. 3; (2017); p. 1831 - 1835 View in Reaxys
NH Br
N
Rx-ID: 1559787 View in Reaxys 2/6 Yield 95 %
Conditions & References 5.1.3. 1-Pentyl-1H-indole (31) 1H-indole (2.50 g, 21.36 mmol) in 20 mL DMF was added to a solution of NaH (60percent dispersion in mineral oil, 1.03 g, 25.63 mmol) in 15 mL DMF, at 5 °C. The mixture was allowed to warm to ambient temperature and was stirred for 30 min. The mixture was cooled to 5 °C and 1-bromopentane (3.17 mL, 25.63 mmol) in 5 mL DMF was added dropwise to the solution, after addition was complete the mixture was allowed to warm to ambient temperature. After 16 h, the mixture was cooled to 5 °C, quenched with 40 mL H2O and extracted with 40 mL Et2O. The aqueous fraction was extracted with Et2O (2 .x. 20 mL) and the combined organic fractions were concentrated in vacuo. Automated flash chromatography (Et2O/petroleum ether 1:19) was used to separate the reaction products, yielding 31 (4.01 g, 95percent yield) as yellow oil. 1H NMR (400 MHz, CDCl3) δ 7.63 (d, J = 7.9 Hz, 1H), 7.34 (d, J = 8.2 Hz, 1H), 7.20 (t, J = 7.6 Hz, 1H), 7.13-7.04 (m, 2H), 6.48 (d, J = 3.0 Hz, 1H), 4.11 (t, J = 7.2 Hz, 2H), 1.90-1.76 (m, 2H), 1.42-1.02 (m, 4H), 0.88 (t, J = 6.9 Hz, 3H). Stage 1: With sodium hydride in N,N-dimethyl-formamide, mineral oil, T= 5 - 20 °C , Inert atmosphere Stage 2: in N,N-dimethyl-formamide, mineral oil, Time= 16h, T= 5 - 20 °C , Inert atmosphere Blaazer, Antoni R.; Lange, Jos H.M.; Van Der Neut, Martina A.W.; Mulder, Arie; Den Boon, Femke S.; Werkman, Taco R.; Kruse, Chris G.; Wadman, Wytse J.; European Journal of Medicinal Chemistry; vol. 46; nb. 10; (2011); p. 5086 - 5098 View in Reaxys
86 %
With potassium hydroxide, tetrabutylammomium bromide, potassium carbonate, Time= 0.0075h, microwave irradiation (300 W) Bogdal, Dariusz; Pielichowski, Jan; Jaskot, Krzysztof; Heterocycles; vol. 45; nb. 4; (1997); p. 715 - 722 View in Reaxys
80 %
Stage 1: With sodium hydride in N,N-dimethyl-formamide, mineral oil, Time= 0.166667h, T= 20 °C , Inert atmosphere Stage 2: in N,N-dimethyl-formamide, mineral oil, T= 0 - 20 °C , Inert atmosphere Banister, Samuel D.; Wilkinson, Shane M.; Longworth, Mitchell; Stuart, Jordyn; Apetz, Nadine; English, Katrina; Brooker, Lance; Goebel, Catrin; Hibbs, David E.; Glass, Michelle; Connor, Mark; McGregor, Iain S.; Kassiou, Michael; ACS Chemical Neuroscience; vol. 4; nb. 7; (2013); p. 1081 - 1092 View in Reaxys With sodium hydride, 1.) DMF, 90 min, 2.) 50-55 deg C, 36 h, Yield given. Multistep reaction Glennon, Richard A.; Chaurasia, Chandra; Titeler, Milt; Journal of Medicinal Chemistry; vol. 33; nb. 10; (1990); p. 2777 - 2784
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 I
N
N
N
S
S
Rx-ID: 4191048 View in Reaxys 3/6 Yield
Conditions & References With 2,2'-azobis(isobutyronitrile), tri-n-butyl-tin hydride in toluene, Time= 4h, Yield given. Yields of byproduct given Caddick, Stephen; Aboutayab, Karim; West, Robert I.; Journal of the Chemical Society, Chemical Communications; nb. 13; (1995); p. 1353 - 1354 View in Reaxys
Br
N
Mg
N
N
N N
Rx-ID: 1607962 View in Reaxys 4/6 Yield
Conditions & References
37 %
in benzene, Time= 25h, Heating Katritzky, Alan R.; Lang, Hengyuan; Lan, Xiangfu; Tetrahedron; vol. 49; nb. 14; (1993); p. 2829 - 2838 View in Reaxys
N
N
N N N
Rx-ID: 3459514 View in Reaxys 5/6 Yield 92 %
Conditions & References With lithium aluminium tetrahydride in toluene, Time= 5.5h, Heating Katritzky, Alan R.; Lang, Hengyuan; Lan, Xiangfu; Tetrahedron; vol. 49; nb. 14; (1993); p. 2829 - 2838 View in Reaxys
N
Rx-ID: 6419456 View in Reaxys 6/6 Yield
Conditions & References Indol, Pentylbromid, NaOH (Phasentransferkatalysator) Barco et al.; Synthesis; (1976); p. 124 View in Reaxys Indol, Pentylbromid <NaOH, Phasentransferkat.> Barco et al.; Synthesis; (1976); p. 124
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
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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