1-Butyl-1H-indole [C12H15N] by Asch

Query

1. Query

Query

Results

Date

54 reactions in Reaxys

2018-03-18 20h:15m:38s (EST)

Search as: As drawn

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NH Br

Rx-ID: 1559589 View in Reaxys 1/54 Yield 99 %

Conditions & References With sodium hydroxide in dimethyl sulfoxide, Time= 2.5h, T= 20 °C , Inert atmosphere Xu, Shuguang; Huang, Xiaomei; Hong, Xiaohu; Xu, Bin; Organic Letters; vol. 14; nb. 17; (2012); p. 4614 - 4617 View in Reaxys

99 %

With sodium hydroxide in dimethyl sulfoxide, Time= 2.5h, T= 20 °C , Inert atmosphere Hong, Xiaohu; Tan, Qitao; Liu, Bingxin; Xu, Bin; Angewandte Chemie - International Edition; vol. 56; nb. 14; (2017); p. 3961 - 3965; Angew. Chem.; vol. 129; nb. 14; (2017); p. 4019 - 4023,5 View in Reaxys

96 %

With potassium hydroxide, PEG-400-Et2 in water, benzene, Time= 2h, T= 30 °C Sukata, Kazuaki; Bulletin of the Chemical Society of Japan; vol. 56; nb. 1; (1983); p. 280 - 284 View in Reaxys

94 %

With potassium hydroxide, 1-butyl-3-methylimidazolium Tetrafluoroborate, Time= 3h, T= 20 °C Le, Zhang-Gao; Chen, Zhen-Chu; Hu, Yi; Zheng, Qin-Guo; Synthesis; nb. 2; (2004); p. 208 - 212 View in Reaxys

94 %

Stage 1: With potassium hydoxide in dimethyl sulfoxide, Time= 0.333333h, T= 20 °C Stage 2: in dimethyl sulfoxide, Time= 0.833333h, T= 35 °C , Sonication Zhao, Sanhu; Kang, Jin; Du, Yuting; Kang, Jingyan; Zhao, Xiaoni; Xu, Yinfeng; Chen, Ruixi; Wang, Qianqian; Shi, Xitao; Journal of Heterocyclic Chemistry; vol. 51; nb. 3; (2014); p. 683 - 689 View in Reaxys

93 %

With potassium hydroxide, 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate, Time= 3h, Ambient temperature Earle, Martyn J.; McCormac, Paul B.; Seddon, Kenneth R.; Chemical Communications; nb. 20; (1998); p. 2245 2246 View in Reaxys

83 %

With sodium hydride in N,N-dimethyl-formamide, mineral oil, Time= 1h, T= 0 - 20 °C , Inert atmosphere Colley, Helen E.; Muthana, Munitta; Danson, Sarah J.; Jackson, Lucinda V.; Brett, Matthew L.; Harrison, Joanne; Coole, Sean F.; Mason, Daniel P.; Jennings, Luke R.; Wong, Melanie; Tulasi, Vamshi; Norman, Dennis; Lockey, Peter M.; Williams, Lynne; Dossetter, Alexander G.; Griffen, Edward J.; Thompson, Mark J.; Journal of Medicinal Chemistry; vol. 58; nb. 23; (2015); p. 9309 - 9333 View in Reaxys

20 %Spectr.

With norbornene, palladium diacetate, caesium carbonate in N,N-dimethyl acetamide, Time= 48h, T= 20 °C , Inert atmosphere, regioselective reaction Jiao, Lei; Bach, Thorsten; Journal of the American Chemical Society; vol. 133; nb. 33; (2011); p. 12990 - 12993 View in Reaxys

19 %Spectr.

With norbornene, potassium carbonate in N,N-dimethyl acetamide, water, Time= 14h, T= 50 °C , Schlenk technique, Inert atmosphere, regioselective reaction Jiao, Lei; Herdtweck, Eberhardt; Bach, Thorsten; Journal of the American Chemical Society; vol. 134; nb. 35; (2012); p. 14563 - 14572 View in Reaxys

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NH N

Rx-ID: 1559728 View in Reaxys 2/54 Yield

Conditions & References

83 %

With potassium tert-butylate, 18-crown-6 ether in diethyl ether, Time= 18h, Ambient temperature Guida, Wayne C.; Mathre, David J.; Journal of Organic Chemistry; vol. 45; nb. 16; (1980); p. 3172 - 3176 View in Reaxys Stage 1: With sodium hydride in N,N-dimethyl-formamide, mineral oil, Time= 0.5h, T= 0 - 20 °C Stage 2: in N,N-dimethyl-formamide, mineral oil, T= 0 - 20 °C Zeng, Fanlong; Alper, Howard; Organic Letters; vol. 15; nb. 8; (2013); p. 2034 - 2037 View in Reaxys Stage 1: With sodium hydride in N,N-dimethyl-formamide, mineral oil, T= 0 °C , Inert atmosphere Stage 2: in N,N-dimethyl-formamide, mineral oil, Inert atmosphere Singh, Rahulkumar Rajmani; Liu, Rai-Shung; Chemical Communications; vol. 53; nb. 33; (2017); p. 4593 - 4596 View in Reaxys

NH N

Rx-ID: 46656674 View in Reaxys 3/54 Yield

Conditions & References

74 %

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 Br

Rx-ID: 46765966 View in Reaxys 4/54 Yield

Conditions & References With tetrakis(triphenylphosphine) palladium(0), caesium carbonate in tetrahydrofuran, Time= 24h, T= 20 °C , Inert atmosphere, Schlenk technique, Irradiation, Overall yield = 31.4 mg Zhou, Wen-Jun; Cao, Guang-Mei; Shen, Guo; Zhu, Xing-Yong; Gui, Yong-Yuan; Ye, Jian-Heng; Sun, Liang; Liao, Li-Li; Li, Jing; Yu, Da-Gang; Angewandte Chemie - International Edition; vol. 56; nb. 49; (2017); p. 15683 15687; Angew. Chem.; vol. 129; nb. 49; (2017); p. 15889 - 15893,5 View in Reaxys

NH N

Rx-ID: 40187636 View in Reaxys 5/54

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Yield

Conditions & References Reaction Steps: 2 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 20 °C / Inert atmosphere 1.2: 20 °C / Inert atmosphere 2.1: [Au2(dppm)2]Cl2; N-ethyl-N,N-diisopropylamine / acetonitrile / 1 h / 20 °C / Inert atmosphere; Irradiation With [Au2(dppm)2]Cl2, sodium hydride, N-ethyl-N,N-diisopropylamine in tetrahydrofuran, acetonitrile, mineral oil Kaldas, Sherif J.; Cannillo, Alexandre; McCallum, Terry; Barriault, Louis; Organic Letters; vol. 17; nb. 11; (2015); p. 2864 - 2866 View in Reaxys Br

Rx-ID: 40187702 View in Reaxys 6/54 Yield

Conditions & References

7 %Spectr., 20 %Spectr., 42 %Spectr.

With [Au2(dppm)2]Cl2, N-ethyl-N,N-diisopropylamine in acetonitrile, Time= 1h, T= 20 °C , Inert atmosphere, Irradiation, Reagent/catalyst, Time Kaldas, Sherif J.; Cannillo, Alexandre; McCallum, Terry; Barriault, Louis; Organic Letters; vol. 17; nb. 11; (2015); p. 2864 - 2866 View in Reaxys

NH N

Rx-ID: 35489367 View in Reaxys 7/54 Yield

Conditions & References With potassium hydoxide in dimethyl sulfoxide, T= 20 °C Yu, Lin; Li, Pinhua; Wang, Lei; Chemical Communications; vol. 49; nb. 23; (2013); p. 2368 - 2370 View in Reaxys Reaction Steps: 2 1: n-butyllithium / diethyl ether / 0.5 h / 25 °C 2: 5 h / 25 °C / Ionic liquid With n-butyllithium in diethyl ether Vavilina; Zicmanis; Drozdova; Mekss; Klavins; Chemistry of Heterocyclic Compounds; vol. 44; nb. 5; (2008); p. 530 - 541; Khim. Geterotsikl. Soedin.; nb. 5; (2008); p. 676 - 690,15 View in Reaxys Reaction Steps: 2 1: n-butyllithium / diethyl ether / 0.5 h / 25 °C 2: 5 h / 25 °C / Ionic liquid With n-butyllithium in diethyl ether Vavilina; Zicmanis; Drozdova; Mekss; Klavins; Chemistry of Heterocyclic Compounds; vol. 44; nb. 5; (2008); p. 530 - 541; Khim. Geterotsikl. Soedin.; nb. 5; (2008); p. 676 - 690,15 View in Reaxys Reaction Steps: 2 1: sodium methylate / methanol / 0.5 h / 25 °C 2: 5 h / 25 °C / Ionic liquid With sodium methylate in methanol

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Vavilina; Zicmanis; Drozdova; Mekss; Klavins; Chemistry of Heterocyclic Compounds; vol. 44; nb. 5; (2008); p. 530 - 541; Khim. Geterotsikl. Soedin.; nb. 5; (2008); p. 676 - 690,15 View in Reaxys Reaction Steps: 2 1: sodium methylate / methanol / 0.5 h / 25 °C 2: 5 h / 25 °C / Ionic liquid With sodium methylate in methanol Vavilina; Zicmanis; Drozdova; Mekss; Klavins; Chemistry of Heterocyclic Compounds; vol. 44; nb. 5; (2008); p. 530 - 541; Khim. Geterotsikl. Soedin.; nb. 5; (2008); p. 676 - 690,15 View in Reaxys Reaction Steps: 2 1: sodium methylate / methanol / 0.5 h / 25 °C 2: 5 h / 25 °C / Ionic liquid With sodium methylate in methanol Vavilina; Zicmanis; Drozdova; Mekss; Klavins; Chemistry of Heterocyclic Compounds; vol. 44; nb. 5; (2008); p. 530 - 541; Khim. Geterotsikl. Soedin.; nb. 5; (2008); p. 676 - 690,15 View in Reaxys

1-halobutane

Rx-ID: 33956862 View in Reaxys 8/54 Yield

Conditions & References Stage 1: With potassium hydoxide in N,N-dimethyl-formamide, Time= 0.5h, T= 20 °C , Inert atmosphere Stage 2: in N,N-dimethyl-formamide, Inert atmosphere Ge, Shao-Peng; Zhang, Xiao-Hong; Han, Jiang-Sheng; Zhong, Ping; Journal of Chemical Research; vol. 36; nb. 6; (2012); p. 356 - 359 View in Reaxys

butyl halide

Rx-ID: 31154691 View in Reaxys 9/54 Yield

Conditions & References Stage 1: With sodium hydroxide in dimethyl sulfoxide Stage 2: in dimethyl sulfoxide, Time= 3h, T= 10 - 15 °C Mirskova; Levkovskaya; Kolesnikova; Perminova; Rudyakova; Adamovich; Russian Chemical Bulletin; vol. 59; nb. 12; (2010); p. 2236 - 2246 View in Reaxys

N– I

Li+

Rx-ID: 1781774 View in Reaxys 10/54 Yield

Conditions & References in tetrahydrofuran, Time= 16h, T= 20 °C , Yield given. Yields of byproduct given

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Nunomoto, Sadaaki; Kawakami, Yuhsuke; Yamashita, Yuya; Takeuchi, Hisato; Eguchi, Shoji; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 1; (1990); p. 111 114 View in Reaxys Time= 5h, T= 25 °C , Ionic liquid Vavilina; Zicmanis; Drozdova; Mekss; Klavins; Chemistry of Heterocyclic Compounds; vol. 44; nb. 5; (2008); p. 530 - 541; Khim. Geterotsikl. Soedin.; nb. 5; (2008); p. 676 - 690,15 View in Reaxys

N– Na +

Rx-ID: 36053107 View in Reaxys 11/54 Yield

Conditions & References Time= 5h, T= 25 °C , Ionic liquid, regioselective reaction Vavilina; Zicmanis; Drozdova; Mekss; Klavins; Chemistry of Heterocyclic Compounds; vol. 44; nb. 5; (2008); p. 530 - 541; Khim. Geterotsikl. Soedin.; nb. 5; (2008); p. 676 - 690,15 View in Reaxys

N– Na +

Rx-ID: 36053108 View in Reaxys 12/54 Yield

N–

Na +

Rx-ID: 36053109 View in Reaxys 13/54 Yield

N– I

Li+

Rx-ID: 36053110 View in Reaxys 14/54 Yield

Conditions & References Time= 5h, T= 25 °C , Ionic liquid

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Vavilina; Zicmanis; Drozdova; Mekss; Klavins; Chemistry of Heterocyclic Compounds; vol. 44; nb. 5; (2008); p. 530 - 541; Khim. Geterotsikl. Soedin.; nb. 5; (2008); p. 676 - 690,15 View in Reaxys

N– I–

Mg2+

Rx-ID: 36053111 View in Reaxys 15/54 Yield

Conditions & References Time= 5h, T= 80 °C , Ionic liquid, regioselective reaction Vavilina; Zicmanis; Drozdova; Mekss; Klavins; Chemistry of Heterocyclic Compounds; vol. 44; nb. 5; (2008); p. 530 - 541; Khim. Geterotsikl. Soedin.; nb. 5; (2008); p. 676 - 690,15 View in Reaxys

N– I–

N N

Mg2+

Rx-ID: 36053112 View in Reaxys 16/54 Yield

N– Na +

Rx-ID: 36053114 View in Reaxys 17/54 Yield

N– Br

Li+

Rx-ID: 36053115 View in Reaxys 18/54 Yield

Conditions & References Time= 5h, T= 25 °C , Ionic liquid Vavilina; Zicmanis; Drozdova; Mekss; Klavins; Chemistry of Heterocyclic Compounds; vol. 44; nb. 5; (2008); p. 530 - 541; Khim. Geterotsikl. Soedin.; nb. 5; (2008); p. 676 - 690,15 View in Reaxys

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N– Li+

Rx-ID: 36053116 View in Reaxys 19/54 Yield

N–

Rx-ID: 36053117 View in Reaxys 20/54 Yield

N–

Li+

Rx-ID: 36053118 View in Reaxys 21/54 Yield

N– I–

Mg2+

Rx-ID: 36053119 View in Reaxys 22/54 Yield

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N– I–

N N

Mg2+

Rx-ID: 36053120 View in Reaxys 23/54 Yield

N– Na +

Rx-ID: 36053122 View in Reaxys 24/54 Yield

N– Li+

Rx-ID: 36053123 View in Reaxys 25/54 Yield

N– Cl

Li+

Rx-ID: 36053124 View in Reaxys 26/54 Yield

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N– I–

N N

Mg2+

Rx-ID: 36053125 View in Reaxys 27/54 Yield

NH N

Rx-ID: 36053131 View in Reaxys 28/54 Yield

Conditions & References Reaction Steps: 2 1: n-butyllithium / diethyl ether / 0.5 h / 25 °C 2: 5 h / 25 °C / Ionic liquid With n-butyllithium in diethyl ether Vavilina; Zicmanis; Drozdova; Mekss; Klavins; Chemistry of Heterocyclic Compounds; vol. 44; nb. 5; (2008); p. 530 - 541; Khim. Geterotsikl. Soedin.; nb. 5; (2008); p. 676 - 690,15 View in Reaxys Reaction Steps: 2 1: n-butyllithium / diethyl ether / 0.5 h / 25 °C 2: 5 h / 25 °C / Ionic liquid With n-butyllithium in diethyl ether Vavilina; Zicmanis; Drozdova; Mekss; Klavins; Chemistry of Heterocyclic Compounds; vol. 44; nb. 5; (2008); p. 530 - 541; Khim. Geterotsikl. Soedin.; nb. 5; (2008); p. 676 - 690,15 View in Reaxys Reaction Steps: 2 1: sodium methylate / methanol / 0.5 h / 25 °C 2: 5 h / 25 °C / Ionic liquid With sodium methylate in methanol Vavilina; Zicmanis; Drozdova; Mekss; Klavins; Chemistry of Heterocyclic Compounds; vol. 44; nb. 5; (2008); p. 530 - 541; Khim. Geterotsikl. Soedin.; nb. 5; (2008); p. 676 - 690,15 View in Reaxys

N N

Rx-ID: 36053132 View in Reaxys 29/54 Yield

Conditions & References Reaction Steps: 2 1: n-butyllithium / diethyl ether / 0.5 h / 25 °C 2: 5 h / 25 °C / Ionic liquid With n-butyllithium in diethyl ether

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Vavilina; Zicmanis; Drozdova; Mekss; Klavins; Chemistry of Heterocyclic Compounds; vol. 44; nb. 5; (2008); p. 530 - 541; Khim. Geterotsikl. Soedin.; nb. 5; (2008); p. 676 - 690,15 View in Reaxys Reaction Steps: 2 1: n-butyllithium / diethyl ether / 0.5 h / 25 °C 2: 5 h / 25 °C / Ionic liquid With n-butyllithium in diethyl ether Vavilina; Zicmanis; Drozdova; Mekss; Klavins; Chemistry of Heterocyclic Compounds; vol. 44; nb. 5; (2008); p. 530 - 541; Khim. Geterotsikl. Soedin.; nb. 5; (2008); p. 676 - 690,15 View in Reaxys Reaction Steps: 2 1: n-butyllithium / diethyl ether / 0.5 h / 25 °C 2: 5 h / 25 °C / Ionic liquid With n-butyllithium in diethyl ether Vavilina; Zicmanis; Drozdova; Mekss; Klavins; Chemistry of Heterocyclic Compounds; vol. 44; nb. 5; (2008); p. 530 - 541; Khim. Geterotsikl. Soedin.; nb. 5; (2008); p. 676 - 690,15 View in Reaxys

N N

Rx-ID: 36053133 View in Reaxys 30/54 Yield

NH Br–

N+

Rx-ID: 36053135 View in Reaxys 31/54 Yield

Conditions & References Stage 1: With iodine, magnesium, methyl iodide in diethyl ether, Time= 0.5h, T= 25 °C Stage 2:Time= 6h, T= 80 °C Vavilina; Zicmanis; Drozdova; Mekss; Klavins; Chemistry of Heterocyclic Compounds; vol. 44; nb. 5; (2008); p. 530 - 541; Khim. Geterotsikl. Soedin.; nb. 5; (2008); p. 676 - 690,15

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View in Reaxys

H N

Rx-ID: 9418788 View in Reaxys 32/54 Yield

Conditions & References With bis(acetylacetonate)nickel(II), sodium t-butanolate, 1,3-bis[2,6-bis(1-methylethyl)phenyl]-1,3-dihydro-2H-imidazol-2-ylidene monohydrochloride in 1,4-dioxane, Time= 7h, T= 100 °C , Title compound not separated from byproducts Omar-Amrani, Rafik; Thomas, Antoine; Brenner, Eric; Schneider, Raphael; Fort, Yves; Organic Letters; vol. 5; nb. 13; (2003); p. 2311 - 2314 View in Reaxys

Rx-ID: 8745769 View in Reaxys 33/54 Yield

Conditions & References

50 %

With potassium tert-butylate, ammonium formate, palladium on activated charcoal in toluene, Time= 5h, T= 120 °C Beller; Breindl; Riermeier; Tillack; Journal of Organic Chemistry; vol. 66; nb. 4; (2001); p. 1403 - 1412 View in Reaxys

Cl N

Rx-ID: 15458393 View in Reaxys 34/54 Yield

Conditions & References Reaction Steps: 2 1.1: n-BuLi / tetrahydrofuran / 3 h / -30 °C 1.2: 43 percent / t-BuOK / toluene / 20 h / 135 °C 2.1: 50 percent / ammonium formate; t-BuOK / Pd/C / toluene / 5 h / 120 °C With n-butyllithium, potassium tert-butylate, ammonium formate, palladium on activated charcoal in tetrahydrofuran, toluene Beller; Breindl; Riermeier; Tillack; Journal of Organic Chemistry; vol. 66; nb. 4; (2001); p. 1403 - 1412 View in Reaxys

Rx-ID: 15458411 View in Reaxys 35/54 Yield

Conditions & References Reaction Steps: 2 1.1: n-BuLi / tetrahydrofuran / 3 h / -30 °C 1.2: 45 percent / t-BuOK / toluene / 20 h / 135 °C 2.1: 50 percent / ammonium formate; t-BuOK / Pd/C / toluene / 5 h / 120 °C With n-butyllithium, potassium tert-butylate, ammonium formate, palladium on activated charcoal in tetrahydrofuran, toluene

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Beller; Breindl; Riermeier; Tillack; Journal of Organic Chemistry; vol. 66; nb. 4; (2001); p. 1403 - 1412 View in Reaxys

H N

Rx-ID: 4898331 View in Reaxys 36/54 Yield

Conditions & References

83 %

With p-benzoquinone, lithium chloride, dichloro bis(acetonitrile) palladium(II) in tetrahydrofuran, Time= 18h, Heating Yamaguchi, Masahiko; Arisawa, Mieko; Hirama, Masahiro; Chemical Communications; nb. 13; (1998); p. 1399 1400 View in Reaxys

H N N

Rx-ID: 16871896 View in Reaxys 37/54 Yield

Conditions & References Reaction Steps: 2 1: 1.) SnCl4, Bu3N, 2.) KOH, H2O / 1.) chlorobenzene, -50 deg C to 80 deg C, 2.) chlorobenzene, THF, reflux 2: 83 percent / quinone, LiCl / PdCl2(MeCN)2 / tetrahydrofuran / 18 h / Heating With potassium hydroxide, tributyl-amine, water, tin(IV) chloride, p-benzoquinone, lithium chloride, dichloro bis(acetonitrile) palladium(II) in tetrahydrofuran Yamaguchi, Masahiko; Arisawa, Mieko; Hirama, Masahiro; Chemical Communications; nb. 13; (1998); p. 1399 1400 View in Reaxys

F O

Rx-ID: 16890819 View in Reaxys 38/54 Yield

Conditions & References Reaction Steps: 2 1: 80 percent / KOH, H2O / methanol / 0.17 h / Heating 2: 83 percent / quinone, LiCl / PdCl2(MeCN)2 / tetrahydrofuran / 18 h / Heating With potassium hydroxide, water, p-benzoquinone, lithium chloride, dichloro bis(acetonitrile) palladium(II) in tetrahydrofuran, methanol Yamaguchi, Masahiko; Arisawa, Mieko; Hirama, Masahiro; Chemical Communications; nb. 13; (1998); p. 1399 1400 View in Reaxys

Rx-ID: 4830752 View in Reaxys 39/54

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Yield

Conditions & References

18 %, 61 %

With triethylamine in benzene, Time= 5h, Irradiation Nishio, Takehiko; Oka, Mitsuru; Helvetica Chimica Acta; vol. 80; nb. 2; (1997); p. 388 - 397 View in Reaxys

Rx-ID: 4833594 View in Reaxys 40/54 Yield

Conditions & References

18 %, 61 %

in benzene, Time= 5h, Irradiation Nishio, Takehiko; Oka, Mitsuru; Helvetica Chimica Acta; vol. 80; nb. 2; (1997); p. 388 - 397 View in Reaxys

H N N

Rx-ID: 4466428 View in Reaxys 41/54 Yield

Conditions & References

70 %

With ruthenium(II) bis(triphenylphosphine) dichloride in 1,4-dioxane, Time= 5h, T= 180 °C Shim; Youn; Lee; Kim; Cho; Uemura; Watanabe; Synthetic Communications; vol. 26; nb. 7; (1996); p. 1349 1353 View in Reaxys I

Rx-ID: 4635715 View in Reaxys 42/54 Yield

Conditions & References

14 %, 33 %, 18 %

With [Ni(1,4,8,11-tetramethyl-1,4,8,11-tetraazacyclotetradecane)](ClO4)2, tetraethylammonium iodide in N,N-dimethyl-formamide, Ambient temperature, electrolysis Ozaki, Shigeko; Mitoh, Shizue; Ohmori, Hidenobu; Chemical and Pharmaceutical Bulletin; vol. 44; nb. 11; (1996); p. 2020 - 2024 View in Reaxys

O N

N O

Rx-ID: 3958619 View in Reaxys 43/54 Yield 85 %

Conditions & References With borane-THF in tetrahydrofuran, Time= 1h, Ambient temperature Pinto, Angelo C.; Silva, Filipe Soares Q. da; Silva, Rosangela B. da; Tetrahedron Letters; vol. 35; nb. 48; (1994); p. 8923 - 8926 View in Reaxys

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NH O

butyl-halide

Rx-ID: 18272329 View in Reaxys 44/54 Yield

Conditions & References Reaction Steps: 2 1: Heating 2: 85 percent / BH3*THF / tetrahydrofuran / 1 h / Ambient temperature With borane-THF in tetrahydrofuran Pinto, Angelo C.; Silva, Filipe Soares Q. da; Silva, Rosangela B. da; Tetrahedron Letters; vol. 35; nb. 48; (1994); p. 8923 - 8926 View in Reaxys

N–

Na +

Rx-ID: 1781775 View in Reaxys 45/54 Yield

Conditions & References in tetrahydrofuran, Time= 16h, T= 20 °C , other indolyl metal salts; other RX (BuOTs, allyl bromide), Product distribution Nunomoto, Sadaaki; Kawakami, Yuhsuke; Yamashita, Yuya; Takeuchi, Hisato; Eguchi, Shoji; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 1; (1990); p. 111 114 View in Reaxys

O S

N–

K+

Rx-ID: 1788061 View in Reaxys 46/54 Yield

Conditions & References

100 %

in tetrahydrofuran, Time= 16h, T= 0 - 20 °C Nunomoto, Sadaaki; Kawakami, Yuhsuke; Yamashita, Yuya; Takeuchi, Hisato; Eguchi, Shoji; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 1; (1990); p. 111 114 View in Reaxys

O S O

N– Br–

Mg2+

Rx-ID: 1788063 View in Reaxys 47/54 Yield

Conditions & References With copper(l) iodide, aluminium trichloride in tetrahydrofuran, Time= 16h, T= -30 °C , Yield given. Yields of byproduct given Nunomoto, Sadaaki; Kawakami, Yuhsuke; Yamashita, Yuya; Takeuchi, Hisato; Eguchi, Shoji; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 1; (1990); p. 111 114

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View in Reaxys

N S

Rx-ID: 2825258 View in Reaxys 48/54 Yield

Conditions & References

77 %

in benzene, Time= 15h, Ambient temperature, Irradiation Nishio; Journal of Organic Chemistry; vol. 53; nb. 6; (1988); p. 1323 - 1326 View in Reaxys

H N HO

Rx-ID: 2860919 View in Reaxys 49/54 Yield

Conditions & References

25 %

With tris(triphenylphosphine)ruthenium(II) chloride in 1,4-dioxane, Time= 5h, T= 180 °C Tsuji, Yasushi; Huh, Keun-Tae; Watanabe, Yoshihisa; Journal of Organic Chemistry; vol. 52; nb. 9; (1987); p. 1673 - 1680 View in Reaxys

S O

Rx-ID: 1559811 View in Reaxys 50/54 Yield

Conditions & References

91 %

With tetraethylammonium tosylate in N,N-dimethyl-formamide, electroreduction Shono, Tatsuya; Kashimura, Shigenori; Nogusa, Hideo; Chemistry Letters; (1986); p. 425 - 428 View in Reaxys

Rx-ID: 1606832 View in Reaxys 51/54 Yield

Conditions & References With lithium diisopropyl amide, 1) diglyme, -78 deg C, 30 min, 2) r.t., 1 h, Yield given. Multistep reaction Ito; Kobayashi; Seko; Saegusa; Bulletin of the Chemical Society of Japan; vol. 57; nb. 1; (1984); p. 73 - 84 View in Reaxys

N Br

H N N

Rx-ID: 3757547 View in Reaxys 52/54

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Yield

Conditions & References

With potassium hydroxide, dibenzo-18-crown-6 in sulfolane, 1.) 90 deg C, 2 h, 2.) 210 deg C, 3 h. Suvorov, N. N.; Plutitskii, D. N.; Smushkevich, Yu. I.; Journal of Organic Chemistry USSR (English Translation); vol. 16; (1980); p. 766 - 769; Zhurnal Organicheskoi Khimii; vol. 16; nb. 4; (1980); p. 872 - 876 View in Reaxys With potassium hydroxide, dibenzo-18-crown-6, methyl iodide, 1) sulfolane, 80 deg C, 2h; 2) 80 deg C, Yield given. Multistep reaction Suvorov, N. N.; Plutitskii, D. N.; Smushkevich, Yu. I.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 17; nb. 3; (1981); p. 268 - 270; Khimiya Geterotsiklicheskikh Soedinenii; vol. 17; nb. 3; (1981); p. 365 - 367 View in Reaxys

Rx-ID: 5427674 View in Reaxys 53/54 Yield

Conditions & References Suga et al.; Bulletin of the Chemical Society of Japan; vol. 42; (1969); p. 3606; Chemistry and Industry (London, United Kingdom); (1969); p. 78 View in Reaxys Ito et al.; Journal of the American Chemical Society; vol. 99; (1977); p. 3532 View in Reaxys Patent; Ciba-Geigy AG; CH556839; (1974); DE2257710; ; vol. 79; nb. 67821 View in Reaxys Jonczyk; Makosza; Roczniki Chemii; vol. 49; (1975); p. 1203 View in Reaxys Ito et al.; Heterocycles; vol. 9; (1978); p. 85 View in Reaxys Suga et al.; Chemistry and Industry (London, United Kingdom); (1969); p. 78 View in Reaxys Plieninger et al.; Chemische Berichte; vol. 108; (1975); p. 1776 View in Reaxys Santaniello et al.; Synthesis; (1979); p. 617 View in Reaxys

indole potassium

Rx-ID: 5427675 View in Reaxys 54/54 Yield

Conditions & References v. Braun; Bayer; Chemische Berichte; vol. 58; (1925); p. 391 View in Reaxys

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