Name: 1078-71-3|N-heptylbenzene|98%
Brand: Ambeed
SKU: A413109
Rating: 91 (32 reviews)

1
[ 108-31-6 ]
[ 1078-71-3 ]
[ 41297-14-7 ]

Yield	Reaction Conditions	Operation in experiment
73%	With Aluminum Chloride In dichloromethane at 0 - 20℃; for 2h;
	With carbon disulfide; aluminium chloride anhydrous

Reference： [1]Kudo, Yudai; Endo, Satoshi; Fujita, Mei; Ota, Atsumi; Kamatari, Yuji O.; Tanaka, Yoshimasa; Ishikawa, Takeshi; Ikeda, Hayato; Okada, Takuya; Toyooka, Naoki; Fujimoto, Naohiro; Matsunaga, Toshiyuki; Ikari, Akira [Journal of Medicinal Chemistry, 2022, vol. 65, # 6, p. 4878 - 4892]
[2]Kirchner; Bailey; Cavallito [Journal of the American Chemical Society, 1949, vol. 71, p. 1210]

2
[ 1671-75-6 ]
[ 1078-71-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium ethanolate; hydrazine hydrate at 180℃;
	With palladium on activated charcoal; ethanol Hydrogenolyse;
	With hydrogenchloride; amalgamated zinc

	With hydrogen; nickel at 300℃;
	With potassium hydroxide; hydrazine
	With potassium hydroxide; hydrazine hydrate; diethylene glycol at 100℃; for 1h;
	Stage #1: Heptanophenone With 1,3-propanedithiol copolymer; boron trifluoride diethyl etherate In chloroform at 0℃; for 10h; Stage #2: With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In toluene at 105℃; for 2.5h;
	With hydrazine
	With hydrogen In tetrahydrofuran at 50℃; for 24h; Autoclave; chemoselective reaction;

Reference： [1]Schmidt; Hopp; Schoeller [Chemische Berichte, 1939, vol. 72, p. 1893,1894]
[2]Ju; Shen; Wood [Journal of the Institute of Petroleum, 1940, vol. 26, p. 514,515]
[3]Fahim; Mustafa [Journal of the Chemical Society, 1949, p. 519] Sulzbacher; Bergmann [Journal of Organic Chemistry, 1948, vol. 13, p. 303,305, 306] Gilman; Meals [Journal of Organic Chemistry, 1943, vol. 8, p. 126,139] Ju; Shen; Wood [Journal of the Institute of Petroleum, 1940, vol. 26, p. 514,515]
[4]Sabatier; Mailhe [Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1914, vol. 158, p. 833]
[5]Asinger,F. et al. [Journal fur praktische Chemie (Leipzig 1954), 1963, vol. 22, p. 153 - 172]
[6]Gamage, Swarna A.; Figgitt, David P.; Wojcik, Stanley J.; Ralph, Raymond K.; Ransijn, Adriana; Mauel, Jacques; Yardley, Vanessa; Snowdon, Diane; Croft, Simon L.; Denny, William A. [Journal of Medicinal Chemistry, 1997, vol. 40, # 16, p. 2634 - 2642]
[7]Bertini, Vincenzo; Lucchesini, Francesco; Pocci, Marco; Alfei, Silvana; De Munno, Angela [Synlett, 2003, # 8, p. 1201 - 1203]
[8]Location in patent: scheme or table Zygadlo; Dardas; Nowicka; Hofmann; Galewski [Molecular Crystals and Liquid Crystals, 2009, vol. 509, # 1, p. 283 - 291]
[9]Location in patent: experimental part Hermannsdoerfer, Justus; Kempe, Rhett [Chemistry - A European Journal, 2011, vol. 17, # 29, p. 8071 - 8077]

3
[ 1078-71-3 ]
[ 5617-41-4 ]

Yield	Reaction Conditions	Operation in experiment
97%	With 10% Pt/activated carbon; isopropyl alcohol In water at 100℃; for 3h; Sealed tube;
96%	With 10% Rh/C; hydrogen In water at 80℃; for 3h;
96.2%	With hydrogen In water at 80℃; for 3.5h; Autoclave;

90%	With nickel(II) oxide; hydrogen; palladium In hexane at 140℃; for 24h;
67%	With diethyl ether for 24h; Milling;
	With acetic acid; platinum Hydrogenation;
	With hydrogen In water at 60℃; for 3h;
	With hydrogen In methanol at 20℃; for 6h;

Reference： [1]Sawama, Yoshinari; Mori, Misato; Yamada, Tsuyoshi; Monguchi, Yasunari; Sajiki, Hironao [Advanced Synthesis and Catalysis, 2015, vol. 357, # 16-17, p. 3667 - 3670]
[2]Location in patent: experimental part Maegawa, Tomohiro; Akashi, Akira; Yaguchi, Kiichiro; Iwasaki, Yohei; Shigetsura, Masahiro; Monguchi, Yasunari; Sajiki, Hironao [Chemistry - A European Journal, 2009, vol. 15, # 28, p. 6953 - 6963]
[3]Shi, Juanjuan; Zhao, Mengsi; Wang, Yingyu; Fu, Jie; Lu, Xiuyang; Hou, Zhaoyin [Journal of Materials Chemistry A, 2016, vol. 4, # 16, p. 5842 - 5848]
[4]Wang, Yanan; Cui, Xinjiang; Deng, Youquan; Shi, Feng [RSC Advances, 2014, vol. 4, # 6, p. 2729 - 2732]
[5]Sawama, Yoshinari; Yasukawa, Naoki; Ban, Kazuho; Goto, Ryota; Niikawa, Miki; Monguchi, Yasunari; Itoh, Miki; Sajiki, Hironao [Organic Letters, 2018, vol. 20, # 10, p. 2892 - 2896]
[6]Schmidt; Grosser [Chemische Berichte, 1940, vol. 73, p. 930,931]
[7]Maegawa, Tomohiro; Akashi, Akira; Sajiki, Hironao [Synlett, 2006, # 9, p. 1440 - 1442]
[8]Location in patent: experimental part Falini, Giuseppe; Gualandi, Andrea; Savoia, Diego [Synthesis, 2009, # 14, p. 2440 - 2446]

4
[ 1078-71-3 ]
[ 16577-10-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; sulfur trioxide
	With sulfuric acid at 55℃; for 2h; Yield given;
	With chlorosulfonic acid In 1,2-dichloro-ethane at 20℃;

Reference： [1]Griess [Fette und Seifen, 1955, vol. 57, p. 236,240]
[2]Rouviere, Jacques; Faucompre, Bernard; Lindheimer, Marc; Partyka, Stanislas; Brun, Bernard [Journal de Chimie Physique et de Physico-Chimie Biologique, 1983, vol. 80, # 3, p. 309 - 314]
[3]Mathevet, Fabrice; Masson, Patrick; Nicoud, Jean-Francois; Skoulios, Antoine [Chemistry - A European Journal, 2002, vol. 8, # 10, p. 2248 - 2254]

5
[ 693-03-8 ]
[ 104-52-9 ]
[ 1078-71-3 ]

Yield	Reaction Conditions	Operation in experiment
	With diethyl ether
100 %Chromat.	In tetrahydrofuran; 1,3-dimethyl-2-imidazolidinone at 20℃; for 0.75h;	2.3 Complex Ih (Example 1, 1 mol %) was subjected to standard alkyl-alkyl Suzuki and Negishi cross-coupling reactions. Reaction conditions are provided in Table 1. The reactions were rapid (Suzuki 5 minutes, Negishi 30 minutes). Quantitative formation of the reaction product was observed at room temperature (Table 1).

Reference： [1]Kharasch; Lambert; Urry [Journal of Organic Chemistry, 1945, vol. 10, p. 298,302]
[2]Current Patent Assignee: TOTAL SYNTHESIS - US2007/73055, 2007, A1 Location in patent: Page/Page column 10; 15

6
[ 1078-71-3 ]
[ 75-36-5 ]
[ 37593-03-6 ]

Yield	Reaction Conditions	Operation in experiment
99%	With aluminium trichloride In dichloromethane at 0 - 20℃;
	With aluminium trichloride; Petroleum ether at 20℃;
	With aluminium trichloride In dichloromethane for 2h; Ambient temperature;

With aluminium trichloride at -20℃;

Reference： [1]Kouwer, Paul H. J.; Jager, Wolter F.; Mijs, Wim J.; Picken, Stephen J. [Journal of Materials Chemistry, 2003, vol. 13, # 3, p. 458 - 469]
[2]Zaki; Fahim [Journal of the Chemical Society, 1942, p. 307] Weygand; Mensdorf [Chemische Berichte, 1935, vol. 68, p. 1825,1832]
[3]Liang, Jason [Journal of Heterocyclic Chemistry, 1984, vol. 21, p. 1297 - 1299]
[4]Ohta, Kazuchika; Jiang, Guang-Jie; Yokoyama, Masaaki; Kusabayashi, Shigekazu; Mikawa, Hiroshi [Molecular Crystals and Liquid Crystals (1969-1991), 1981, vol. 66, p. 283 - 294]

7
[ 79-37-8 ]
[ 1078-71-3 ]
[ 50606-96-7 ]

Yield	Reaction Conditions	Operation in experiment
79.3%	Stage #1: oxalyl dichloride With aluminum (III) chloride In dichloromethane for 0.0833333h; Stage #2: heptylbenzene In dichloromethane at 20 - 25℃; for 1h;
	With aluminium trichloride In Trichloroethylene for 0.5h; Ambient temperature;

Reference： [1]Neubert, Mary E.; Fishel [Organic Syntheses, 1983, vol. 61, p. 8 - 8]
[2]Osman, Maged A. [Helvetica Chimica Acta, 1982, vol. 65, # 8, p. 2448 - 2449]
[3]Tinh; Pourrere; Destrade [Molecular Crystals and Liquid Crystals (1969-1991), 1980, vol. 62, # 1-2, p. 125 - 139]

8
1-phenylhept-1-ene [ No CAS ]
[ 1078-71-3 ]

Yield	Reaction Conditions	Operation in experiment
71%	With chloro-trimethyl-silane; benzoic acid; sodium iodide In acetonitrile at 75℃; for 20h;

Reference： [1]Ghera, Eugene; Maurya, Rakesh; Hassner, Alfred [Tetrahedron Letters, 1989, vol. 30, # 35, p. 4741 - 4744]

9
[ 87764-08-7 ]
[ 1078-71-3 ]
trans-1-phenyl-2-methylcyclohexane [ No CAS ]
cis-1-phenyl-2-methylcyclohexane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 80% 2: 0.14% 3: 20%	With hydrogen In cyclohexane

Reference： [1]Marvell, Elliot N.; Hilton, Charles; Tilton, Mary [Journal of Organic Chemistry, 1983, vol. 48, # 26, p. 5379 - 5381]

10
1-cyclopropyl-4-phenyl-4-(phenylthio)-1-butene [ No CAS ]
[ 1078-71-3 ]
1-cyclopropyl-4-phenylbutane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 52% 2: 24%	With sodium tetrahydroborate; nickel dichloride In tetrahydrofuran; methanol at 0℃; for 0.25h;

Reference： [1]Back, Thomas G.; Baron, Denise L.; Yang, Kexin [Journal of Organic Chemistry, 1993, vol. 58, # 9, p. 2407 - 2413]

11
[ 1078-71-3 ]
[ 625-36-5 ]
[ 178267-78-2 ]

Yield	Reaction Conditions	Operation in experiment
67%	With aluminium trichloride In pentane at 20℃; for 1h;

Reference： [1]Brettle, Roger; Dunmur, David A.; Farrand, Louise D.; Marson, Charles M. [Journal of Materials Chemistry, 1996, vol. 6, # 5, p. 747 - 751]

12
[ 24767-82-6 ]
[ 108-86-1 ]
[ 1078-71-3 ]

Yield	Reaction Conditions	Operation in experiment
	With CuBr*Me₂S-LiBr; lithium thiophenoxide; magnesium 1) THF, reflux; 2) THF, HMPA, rt, 24 h; further reagents and conditions; Yield given. Multistep reaction;

Reference： [1]Burns, Dennis H.; Miller, Jeffrey D.; Chan, Ho-Kit; Delaney, Michael O. [Journal of the American Chemical Society, 1997, vol. 119, # 9, p. 2125 - 2133]

13
[ 19969-03-0 ]
[ 1078-71-3 ]

Yield	Reaction Conditions	Operation in experiment
80%	With 2,2-dimethyl-propanol-1; 2-nitrobenzenesulfonyl hydrazide; triphenylphosphine; diethylazodicarboxylate In various solvent(s)
35%	Stage #1: 1-phenylheptan-3-ol With N-isopropylidene-N’-2-nitrobenzenesulfonyl hydrazine; triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 23℃; for 0.416667h; Stage #2: With phenylhydrazine In tetrahydrofuran at 23℃; for 13h;

Reference： [1]Myers; Movassaghi; Zheng [Journal of the American Chemical Society, 1997, vol. 119, # 36, p. 8572 - 8573]
[2]Movassaghi, Mohammad; Ahmad, Omar K. [Journal of Organic Chemistry, 2007, vol. 72, # 5, p. 1838 - 1841]

14
[ 80471-71-2 ]
[ 1078-71-3 ]
C₁₃H₂₀⁽¹⁸⁾O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With 2,2'-azobis(isobutyronitrile); tributyltin chloride; sodium cyanoborohydride; oxygen-18 In <i>tert</i>-butyl alcohol at 60℃; for 15h; Yields of byproduct given;

Reference： [1]Sawamura, Masaya; Kawaguchi, Yasuhide; Nakamura, Eiichi [Synlett, 1997, vol. 1997, # 7, p. 801 - 802]

15
[ 24767-82-6 ]
[ 71-43-2 ]
heptan-3-ylbenzene [ No CAS ]
[ 2132-84-5 ]
[ 1078-71-3 ]
[ 2132-86-7 ]

Yield	Reaction Conditions	Operation in experiment
	at 85℃; for 5h;

Reference： [1]Badr, M. Z. A.; El-Naggar, G. M.; Aly, M. M.; Fahmy, A. M. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1980, vol. 19, # 11, p. 961 - 964]

16
[ 1078-71-3 ]
[ 76287-49-5 ]

Reference： [1]Journal of Materials Chemistry,2001,vol. 11,p. 1063 - 1071

17
[ 19969-04-1 ]
[ 1078-71-3 ]

Yield	Reaction Conditions	Operation in experiment
90%	With polymethylhydrosiloxane; tris(pentafluorophenyl)borate In dichloromethane at 20℃;

Reference： [1]Chandrasekhar; Raji Reddy, Ch.; Nagendra Babu [Journal of Organic Chemistry, 2002, vol. 67, # 25, p. 9080 - 9082]

18
[ 3742-75-4 ]
[ 24406-16-4 ]
[ 1078-71-3 ]

Yield	Reaction Conditions	Operation in experiment
92%	In diethyl ether at -20℃; for 0.5h;

Reference： [1]Suenaga, Toshiro; Schutz, Caroline; Nakata, Tadashi [Tetrahedron Letters, 2003, vol. 44, # 31, p. 5799 - 5801]

19
[ 24406-16-4 ]
[ 601488-42-0 ]
[ 1078-71-3 ]

Yield	Reaction Conditions	Operation in experiment
92%	In diethyl ether at -20℃; for 0.5h;

Reference： [1]Suenaga, Toshiro; Schutz, Caroline; Nakata, Tadashi [Tetrahedron Letters, 2003, vol. 44, # 31, p. 5799 - 5801]

20
[ 3277-89-2 ]
[ 71-41-0 ]
[ 1078-71-3 ]

Yield	Reaction Conditions	Operation in experiment
78%	Stage #1: pentan-1-ol With n-butyllithium; chloro-diphenylphosphine In tetrahydrofuran Stage #2: With methyl iodide In tetrahydrofuran at 20℃; for 1h; Stage #3: phenethylmagnesium bromide In tetrahydrofuran at 20℃; for 1h;

Reference： [1]Shintou, Taichi; Kikuchi, Wataru; Mukaiyama, Teruaki [Chemistry Letters, 2003, vol. 32, # 8, p. 676 - 677]

21
[ 24767-82-6 ]
phenylmagnesium bromide [ No CAS ]
[ 142-82-5 ]
[ 1078-71-3 ]

Yield	Reaction Conditions	Operation in experiment
1: 85 % Chromat. 2: 3 % Chromat.	With buta-1,3-diene In tetrahydrofuran at 25℃; for 3h;

Reference： [1]Terao, Jun; Naitoh, Yoshitaka; Kuniyasu, Hitoshi; Kambe, Nobuaki [Chemistry Letters, 2003, vol. 32, # 10, p. 890 - 891]

22
[ 3761-92-0 ]
[ 100-51-6 ]
[ 1078-71-3 ]

Yield	Reaction Conditions	Operation in experiment
89%	Stage #1: benzyl alcohol With n-butyllithium; chloro-diphenylphosphine In tetrahydrofuran Stage #2: With methyl iodide In tetrahydrofuran at 20℃; for 1h; Stage #3: n-hexylmagnesium bromide In tetrahydrofuran at 20℃; for 1h;

Reference： [1]Shintou, Taichi; Kikuchi, Wataru; Mukaiyama, Teruaki [Chemistry Letters, 2003, vol. 32, # 8, p. 676 - 677]

23
[ 1589-82-8 ]
[ 111-27-3 ]
[ 1078-71-3 ]

Yield	Reaction Conditions	Operation in experiment
80%	Stage #1: hexan-1-ol With n-butyllithium; chloro-diphenylphosphine In tetrahydrofuran Stage #2: With methyl iodide In tetrahydrofuran at 20℃; for 1h; Stage #3: phenylmagnesium bromide In tetrahydrofuran at 20℃; for 1h;

Reference： [1]Shintou, Taichi; Kikuchi, Wataru; Mukaiyama, Teruaki [Chemistry Letters, 2003, vol. 32, # 8, p. 676 - 677]

24
[ 637-59-2 ]
[ 92273-73-9 ]
[ 1078-71-3 ]

Yield	Reaction Conditions	Operation in experiment
85%	With 4,5-dihydroimidazolium NHC ligand In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 20℃; for 24h;
85%	With tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 20℃; for 24h;
77 % Chromat.	In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 20℃; for 18h;

100 % Chromat.	In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 20℃; for 0.5h;
100 %Chromat.	With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl) palladium(II) dichloride; lithium bromide In tetrahydrofuran; desipramine at 20℃; for 2h; Inert atmosphere;
	With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl) palladium(II) dichloride In tetrahydrofuran; 1,3-dimethyl-2-imidazolidinone at 20℃; for 2h; Inert atmosphere;
100 %Chromat.	In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 20℃; for 24h;	2.1 Complex Ih (Example 1, 1 mol %) was subjected to standard alkyl-alkyl Suzuki and Negishi cross-coupling reactions. Reaction conditions are provided in Table 1. The reactions were rapid (Suzuki 5 minutes, Negishi 30 minutes). Quantitative formation of the reaction product was observed at room temperature (Table 1).
34 %Chromat.	In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 20℃; for 24h;	2.1 Complex Ih (Example 1, 1 mol %) was subjected to standard alkyl-alkyl Suzuki and Negishi cross-coupling reactions. Reaction conditions are provided in Table 1. The reactions were rapid (Suzuki 5 minutes, Negishi 30 minutes). Quantitative formation of the reaction product was observed at room temperature (Table 1).
8 %Chromat.	In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 20℃; for 24h;	2.1 Complex Ih (Example 1, 1 mol %) was subjected to standard alkyl-alkyl Suzuki and Negishi cross-coupling reactions. Reaction conditions are provided in Table 1. The reactions were rapid (Suzuki 5 minutes, Negishi 30 minutes). Quantitative formation of the reaction product was observed at room temperature (Table 1).
98 %Chromat.	With C₃₂H₄₀Br₃N₃Pd; lithium bromide In tetrahydrofuran; 1,3-dimethyl-2-imidazolidinone at 20℃; for 24h; Inert atmosphere;
	With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl) palladium(II) dichloride; lithium bromide In tetrahydrofuran; 1,3-dimethyl-2-imidazolidinone at 20℃; for 2h; Inert atmosphere; chemoselective reaction;
100 %Chromat.	With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II) dichloride; lithium bromide In tetrahydrofuran; 1,3-dimethyl-2-imidazolidinone at 20℃; for 2h;

Reference： [1]O'Brien, Christopher J.; Kantchev, Eric Assen B.; Chass, Gregory A.; Hadei, Niloufar; Hopkinson, Alan C.; Organ, Michael G.; Setiadi, David H.; Tang, Ting-Hua; Fang, De-Cai [Tetrahedron, 2005, vol. 61, # 41, p. 9723 - 9735]
[2]Hadei, Niloufar; Kantchev, Eric Assen B.; O'Brien, Christopher J.; Organ, Michael G. [Journal of Organic Chemistry, 2005, vol. 70, # 21, p. 8503 - 8507]
[3]Hadei, Niloufar; Kantchev, Eric Assen B.; O'Brien, Christopher J.; Organ, Michael G. [Organic Letters, 2005, vol. 7, # 17, p. 3805 - 3807]
[4]O'Brien, Christopher J.; Kantchev, Eric Assen B.; Valente, Cory; Hadei, Niloufar; Chass, Gregory A.; Lough, Alan; Hopkinson, Alan C.; Organ, Michael G. [Chemistry - A European Journal, 2006, vol. 12, # 18, p. 4743 - 4748]
[5]Location in patent: experimental part Chass, Gregory A.; O'Brien, Christopher J.; Hadei, Niloufar; Kantchev, Eric Assen B.; Mu, Wei-Hua; Fang, De-Cai; Hopkinson, Alan C.; Csizmadia, Imre G.; Organ, Michael G. [Chemistry - A European Journal, 2009, vol. 15, # 17, p. 4281 - 4288]
[6]Achonduh, George T.; Hadei, Niloufar; Valente, Cory; Avola, Stephanie; O'Brien, Christopher J.; Organ, Michael G. [Chemical Communications, 2010, vol. 46, # 23, p. 4109 - 4111]
[7]Current Patent Assignee: TOTAL SYNTHESIS - US2007/73055, 2007, A1 Location in patent: Page/Page column 10; 15
[8]Current Patent Assignee: TOTAL SYNTHESIS - US2007/73055, 2007, A1 Location in patent: Page/Page column 10; 15
[9]Current Patent Assignee: TOTAL SYNTHESIS - US2007/73055, 2007, A1 Location in patent: Page/Page column 10; 15
[10]Nasielski, Joanna; Hadei, Nilofaur; Achonduh, George; Kantchev, Eric Assen B.; O'Brien, Christopher J.; Lough, Alan; Organ, Michael G. [Chemistry - A European Journal, 2010, vol. 16, # 35, p. 10844 - 10853]
[11]Hadei, Niloufar; Achonduh, George T.; Valente, Cory; O'Brien, Christopher J.; Organ, Michael G. [Angewandte Chemie - International Edition, 2011, vol. 50, # 17, p. 3896 - 3899]
[12]Location in patent: scheme or table Hunter, Howard N.; Hadei, Niloufar; Blagojevic, Voislav; Patschinski, Pascal; Achonduh, George T.; Avola, Stephanie; Bohme, Diethard K.; Organ, Michael G. [Chemistry - A European Journal, 2011, vol. 17, # 28, p. 7845 - 7851]

25
[ 122-56-5 ]
[ 637-59-2 ]
[ 1078-71-3 ]

Yield	Reaction Conditions	Operation in experiment
100 % Chromat.	With potassium <i>tert</i>-butylate In isopropyl alcohol at 20℃; for 0.0833333h;
100 %Chromat.	With potassium <i>tert</i>-butylate In isopropyl alcohol at 20℃; for 24h;	2.2 Complex Ih (Example 1, 1 mol %) was subjected to standard alkyl-alkyl Suzuki and Negishi cross-coupling reactions. Reaction conditions are provided in Table 1. The reactions were rapid (Suzuki 5 minutes, Negishi 30 minutes). Quantitative formation of the reaction product was observed at room temperature (Table 1).
31 %Chromat.	With potassium <i>tert</i>-butylate In isopropyl alcohol at 20℃; for 24h;	2.2 Complex Ih (Example 1, 1 mol %) was subjected to standard alkyl-alkyl Suzuki and Negishi cross-coupling reactions. Reaction conditions are provided in Table 1. The reactions were rapid (Suzuki 5 minutes, Negishi 30 minutes). Quantitative formation of the reaction product was observed at room temperature (Table 1).

6.5 %Chromat.

With potassium tert-butylate In isopropyl alcohol at 20℃; for 24h;

2.2 Complex Ih (Example 1, 1 mol %) was subjected to standard alkyl-alkyl Suzuki and Negishi cross-coupling reactions. Reaction conditions are provided in Table 1. The reactions were rapid (Suzuki 5 minutes, Negishi 30 minutes). Quantitative formation of the reaction product was observed at room temperature (Table 1).

Reference： [1]O'Brien, Christopher J.; Kantchev, Eric Assen B.; Valente, Cory; Hadei, Niloufar; Chass, Gregory A.; Lough, Alan; Hopkinson, Alan C.; Organ, Michael G. [Chemistry - A European Journal, 2006, vol. 12, # 18, p. 4743 - 4748]
[2]Current Patent Assignee: TOTAL SYNTHESIS - US2007/73055, 2007, A1 Location in patent: Page/Page column 10; 15
[3]Current Patent Assignee: TOTAL SYNTHESIS - US2007/73055, 2007, A1 Location in patent: Page/Page column 10; 15
[4]Current Patent Assignee: TOTAL SYNTHESIS - US2007/73055, 2007, A1 Location in patent: Page/Page column 10; 15

26
[ 629-06-1 ]
[ 1078-71-3 ]

Yield	Reaction Conditions	Operation in experiment
70 % Chromat.	With zinc(II) chloride In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 20℃; for 24h;

Reference： [1]Organ, Michael G.; Avola, Stephanie; Dubovyk, Igor; Hadei, Niloufar; Kantchev, Eric Assen B.; O'Brien, Christopher J.; Valente, Gory [Chemistry - A European Journal, 2006, vol. 12, # 18, p. 4749 - 4755]

27
[ 629-04-9 ]
[ 1078-71-3 ]

Yield	Reaction Conditions	Operation in experiment
100 % Chromat.	With lithium bromide; zinc(II) chloride In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 20℃; for 24h;

Reference： [1]Organ, Michael G.; Avola, Stephanie; Dubovyk, Igor; Hadei, Niloufar; Kantchev, Eric Assen B.; O'Brien, Christopher J.; Valente, Gory [Chemistry - A European Journal, 2006, vol. 12, # 18, p. 4749 - 4755]

28
[ 4282-40-0 ]
[ 1078-71-3 ]

Yield	Reaction Conditions	Operation in experiment
100 % Chromat.	With zinc(II) chloride In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 20℃; for 24h;

Reference： [1]Organ, Michael G.; Avola, Stephanie; Dubovyk, Igor; Hadei, Niloufar; Kantchev, Eric Assen B.; O'Brien, Christopher J.; Valente, Gory [Chemistry - A European Journal, 2006, vol. 12, # 18, p. 4749 - 4755]

29
[ 24767-82-6 ]
[ 1078-71-3 ]

Yield	Reaction Conditions	Operation in experiment
90 % Chromat.	With zinc(II) chloride In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 20℃; for 24h;

Reference： [1]Organ, Michael G.; Avola, Stephanie; Dubovyk, Igor; Hadei, Niloufar; Kantchev, Eric Assen B.; O'Brien, Christopher J.; Valente, Gory [Chemistry - A European Journal, 2006, vol. 12, # 18, p. 4749 - 4755]

30
[ 16156-51-7 ]
[ 1078-71-3 ]

Yield	Reaction Conditions	Operation in experiment
87 % Chromat.	With zinc(II) chloride In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 20℃; for 24h;

Reference： [1]Organ, Michael G.; Avola, Stephanie; Dubovyk, Igor; Hadei, Niloufar; Kantchev, Eric Assen B.; O'Brien, Christopher J.; Valente, Gory [Chemistry - A European Journal, 2006, vol. 12, # 18, p. 4749 - 4755]

31
[ 104-52-9 ]
[ 1078-71-3 ]

Yield	Reaction Conditions	Operation in experiment
88 % Chromat.	With lithium bromide In tetrahydrofuran at 20℃; for 24h;

Reference： [1]Organ, Michael G.; Avola, Stephanie; Dubovyk, Igor; Hadei, Niloufar; Kantchev, Eric Assen B.; O'Brien, Christopher J.; Valente, Gory [Chemistry - A European Journal, 2006, vol. 12, # 18, p. 4749 - 4755]

32
[ 637-59-2 ]
[ 1078-71-3 ]

Yield	Reaction Conditions	Operation in experiment
100 % Chromat.	With lithium bromide In tetrahydrofuran at 20℃; for 24h;

Reference： [1]Organ, Michael G.; Avola, Stephanie; Dubovyk, Igor; Hadei, Niloufar; Kantchev, Eric Assen B.; O'Brien, Christopher J.; Valente, Gory [Chemistry - A European Journal, 2006, vol. 12, # 18, p. 4749 - 4755]

33
[ 4119-41-9 ]
[ 1078-71-3 ]

Yield	Reaction Conditions	Operation in experiment
68 % Chromat.	With lithium bromide In tetrahydrofuran at 20℃; for 24h;

Reference： [1]Organ, Michael G.; Avola, Stephanie; Dubovyk, Igor; Hadei, Niloufar; Kantchev, Eric Assen B.; O'Brien, Christopher J.; Valente, Gory [Chemistry - A European Journal, 2006, vol. 12, # 18, p. 4749 - 4755]

34
[ 3742-75-4 ]
[ 1078-71-3 ]

Yield	Reaction Conditions	Operation in experiment
100 % Chromat.	With lithium bromide In tetrahydrofuran at 20℃; for 24h;

Reference： [1]Organ, Michael G.; Avola, Stephanie; Dubovyk, Igor; Hadei, Niloufar; Kantchev, Eric Assen B.; O'Brien, Christopher J.; Valente, Gory [Chemistry - A European Journal, 2006, vol. 12, # 18, p. 4749 - 4755]

35
[ 69804-99-5 ]
[ 1078-71-3 ]

Yield	Reaction Conditions	Operation in experiment
100 % Chromat.	With lithium bromide In tetrahydrofuran at 20℃; for 24h;

Reference： [1]Organ, Michael G.; Avola, Stephanie; Dubovyk, Igor; Hadei, Niloufar; Kantchev, Eric Assen B.; O'Brien, Christopher J.; Valente, Gory [Chemistry - A European Journal, 2006, vol. 12, # 18, p. 4749 - 4755]

36
[ 17763-67-6 ]
[ 1078-71-3 ]

Yield	Reaction Conditions	Operation in experiment
100 % Chromat.	With lithium bromide In tetrahydrofuran at 20℃; for 24h;

Reference： [1]Organ, Michael G.; Avola, Stephanie; Dubovyk, Igor; Hadei, Niloufar; Kantchev, Eric Assen B.; O'Brien, Christopher J.; Valente, Gory [Chemistry - A European Journal, 2006, vol. 12, # 18, p. 4749 - 4755]

37
[ 108-90-7 ]
[ 1078-71-3 ]

Yield	Reaction Conditions	Operation in experiment
100 % Chromat.	With lithium chloride In tetrahydrofuran at 20℃; for 24h;

Reference： [1]Organ, Michael G.; Avola, Stephanie; Dubovyk, Igor; Hadei, Niloufar; Kantchev, Eric Assen B.; O'Brien, Christopher J.; Valente, Gory [Chemistry - A European Journal, 2006, vol. 12, # 18, p. 4749 - 4755]

38
[ 108-86-1 ]
[ 1078-71-3 ]

Yield	Reaction Conditions	Operation in experiment
100 % Chromat.	With lithium bromide In tetrahydrofuran at 20℃; for 24h;

Reference： [1]Organ, Michael G.; Avola, Stephanie; Dubovyk, Igor; Hadei, Niloufar; Kantchev, Eric Assen B.; O'Brien, Christopher J.; Valente, Gory [Chemistry - A European Journal, 2006, vol. 12, # 18, p. 4749 - 4755]

39
[ 591-50-4 ]
[ 1078-71-3 ]

Yield	Reaction Conditions	Operation in experiment
95 % Chromat.	With lithium chloride In tetrahydrofuran at 20℃; for 24h;

Reference： [1]Organ, Michael G.; Avola, Stephanie; Dubovyk, Igor; Hadei, Niloufar; Kantchev, Eric Assen B.; O'Brien, Christopher J.; Valente, Gory [Chemistry - A European Journal, 2006, vol. 12, # 18, p. 4749 - 4755]

40
[ 1078-71-3 ]
[ 37529-27-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 150 mg / HNO₃ / 24 h / 20 °C 2: H₂ / Pt/C / methanol
	Stage #1: heptylbenzene With aluminum (III) chloride; acetyl chloride Stage #2:

Reference： [1]Gamage, Swarna A.; Figgitt, David P.; Wojcik, Stanley J.; Ralph, Raymond K.; Ransijn, Adriana; Mauel, Jacques; Yardley, Vanessa; Snowdon, Diane; Croft, Simon L.; Denny, William A. [Journal of Medicinal Chemistry, 1997, vol. 40, # 16, p. 2634 - 2642]
[2]Location in patent: scheme or table Zygadlo; Dardas; Nowicka; Hofmann; Galewski [Molecular Crystals and Liquid Crystals, 2009, vol. 509, # 1, p. 283 - 291]

41
[ 1078-71-3 ]
9-[(4-heptylphenyl)amino]acridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 150 mg / HNO₃ / 24 h / 20 °C 2: H₂ / Pt/C / methanol 3: aq. HCl / methanol / 0.5 h / Ambient temperature

Reference： [1]Gamage, Swarna A.; Figgitt, David P.; Wojcik, Stanley J.; Ralph, Raymond K.; Ransijn, Adriana; Mauel, Jacques; Yardley, Vanessa; Snowdon, Diane; Croft, Simon L.; Denny, William A. [Journal of Medicinal Chemistry, 1997, vol. 40, # 16, p. 2634 - 2642]

42
[ 588-73-8 ]
[ 1078-71-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: bis(triphenylphosphine)dichloropalladium(II), cuprous iodide / diethylamine / 6 h 2: 54 percent / H₂ / Lindlar / cyclohexane 3: 54 percent / cyclohexane / 50 h / 150 °C 4: 16 percent Chromat_. / H₂ / platinum oxide / cyclohexane

Reference： [1]Marvell, Elliot N.; Hilton, Charles; Tilton, Mary [Journal of Organic Chemistry, 1983, vol. 48, # 26, p. 5379 - 5381]

43
[ 588-72-7 ]
[ 1078-71-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: bis(triphenylphosphine)dichloropalladium(II), cuprous iodide / diethylamine / 6 h 2: H₂, synthetic quinoline / Lindlar / cyclohexane 3: cyclohexane / 3 h / 135 °C 4: 20 percent / H₂ / platinum oxide / cyclohexane

Reference： [1]Marvell, Elliot N.; Hilton, Charles; Tilton, Mary [Journal of Organic Chemistry, 1983, vol. 48, # 26, p. 5379 - 5381]

44
[ 3893-05-8 ]
[ 1078-71-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: cyclohexane / 3 h / 135 °C 2: 20 percent / H₂ / platinum oxide / cyclohexane

Reference： [1]Marvell, Elliot N.; Hilton, Charles; Tilton, Mary [Journal of Organic Chemistry, 1983, vol. 48, # 26, p. 5379 - 5381]

45
[ 87764-07-6 ]
[ 1078-71-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 54 percent / cyclohexane / 50 h / 150 °C 2: 16 percent Chromat_. / H₂ / platinum oxide / cyclohexane

Reference： [1]Marvell, Elliot N.; Hilton, Charles; Tilton, Mary [Journal of Organic Chemistry, 1983, vol. 48, # 26, p. 5379 - 5381]

46
[ 106-31-0 ]
[ 1078-71-3 ]
[ 52055-23-9 ]
[ 224180-91-0 ]

Yield	Reaction Conditions	Operation in experiment
0.25 g (74%)	With hydrogenchloride; sodium hydrogencarbonate; triethylamine; sodium chloride In dichloromethane	2 N-[2-(5-Benzyloxyindol-3-yl)ethyl] butanamide (DNAS-18 or CA-18) Example 2 N-[2-(5-Benzyloxyindol-3-yl)ethyl] butanamide (DNAS-18 or CA-18) Butyric anhydride (0.2 ml, 1.2 mmol) was added dropwise at room temperature to a well-stirred mixture of 5-benzyloxytryptamine hydrochloride (0.3 g, 1 mmol), Et3N (0.35 ml, 2.5 mmol) and CH2Cl2 (3 ml). After stirring for 40 h at 30-35° C. the reaction mixture was washed with water (25 ml), 5% solution of NaHCO3 (210 ml), 1% solution of HCl (5 ml) and then saturated solution of NaCl (10 ml). After drying over Na2SO4, the solvent was evaporated. Recrystallization of residue from benzene-heptane gave a yield of 0.25 g (74%) of N-[2-(5-benzyloxyindol-3-yl)ethyl]butanamide: mp 112-114° C. 1H NMR(CDCl3, ppm, δ): 0.90(3H, t, CH2CH3, J=8 Hz), 1.39(2H, m CH2CH2 CH3), 2.07(2H, t, CH2CH2 CH3, J=8 Hz), 2.92(2H, t, β-CH2, J=7 Hz), 3.56 (2H, q, α-CH2, J=6.5 Hz), 5.05(2H, s, CH2-O); 5.63(1H, bs, NH), 6.90-7.00(2H, m, 2- and 6-H), 7.10(1H, d, 4-H, J4-6=2 Hz), 7.20-7.48(6H, m, 7-H and Ph), 8.24(1H, bs, 1-H). Found, %: C 75.23; H 6.95; N 8.37. C21H24N2O2. Calc., %: C 75.0; H 7.14; N 8.33%.

Reference： [1]Current Patent Assignee: STEWARD RESEARCH AND SPECIALTY PROJECTS CORPORATION - US6353015, 2002, B1

47
[ 1078-71-3 ]
[ 52055-23-9 ]
[ 224180-90-9 ]

Yield	Reaction Conditions	Operation in experiment
0.515 g (80%)	With hydrogenchloride; sodium hydrogencarbonate; triethylamine; sodium chloride In dichloromethane; propionic acid anhydride	1 N-[2-(5-Benzyloxyindol-3-yl)ethyl]propanamide (DNAS-15 or CA-15) Example 1 N-[2-(5-Benzyloxyindol-3-yl)ethyl]propanamide (DNAS-15 or CA-15) Propionic anhydride (0.3 ml, 2.3 mmol) was added dropwise at room temperature to a well-stirred mixture of 5-benzyloxytryptamine hydrochloride (0.605 g, 2 mmol), Et3N (0.65 ml, 4.6 mmol) and CH2Cl2 (5 ml). After stirring for 24 h, the reaction mixture was washed with water (2.5 ml), 5% solution of NaHCO3 (10 ml), 1% solution of HCl (5 ml) and then saturated solution of NaCl (10 ml). After drying over Na2SO4, the solvent was evaporated. Recrystallization of residue from benzene-heptane gave a yield of 0.515 g (80%) of N-[2-(5-benzyloxyindol-3-yl)ethyl]propanamide: mp 110-112° C. 1H NMR(CDCl3, ppm, δ): 1.11(3H, t, CH2CH3, J=8 Hz), 2.13(2H, q, CH2CH3), 2.90(2H, t, β-CH2, J=6.7 Hz), 3.58 (2H, q, α-CH2, J=6.2 Hz), 5.10(2H, s, CH2-O), 5.59(1H, bs, NH), 6.86-7.04(2H, m, 2- and 6-H), 7.13(1H, d, 4-H, J4-6=2Hz), 7.25-7.68(6H, m 7-H and Ph), 8.15(1H, bs, 1-H). Found, %: C 74.23; H 6.75; N 8.77. C20H22N2O2. Calc., %: C 74.53; H 6.83; N 8.70%.

Reference： [1]Current Patent Assignee: STEWARD RESEARCH AND SPECIALTY PROJECTS CORPORATION - US6353015, 2002, B1

48
[ 111-16-0 ]
[ 1078-71-3 ]
[ 178686-98-1 ]