3-(2-bromoethyl)-1H-indole

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2016-06-11 19h:55m:14s (EST)

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2016-06-11 19h:55m:40s (EST)

Br

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NH

NH

OH

Br

Rx-ID: 113009 View in Reaxys 1/6 Yield 95 %

Conditions & References With triphenylphosphine monolith functionalized with carbon tetrabromide in dichloromethane, T= 0 °C , p= 5171.62Torr , Flow reactor, Appel Halogenation Roper, Kimberley A.; Berry, Malcolm B.; Ley, Steven V.; Beilstein Journal of Organic Chemistry; vol. 9; (2013); p.

1781 - 1790 View in Reaxys

95 %

3-(2-Bromoethyl)-1H-indole (3a) In a three-neck flask, tryptophol (2.00 g, 1 eq.) and triphenylphosphine (4.23 g, 1.3 eq.) was dissolved in dry CH2Cl2 (15 ml). In an addition funnel, carbon tetrabromide (5.35 g, 1.3 eq.) dissolved in dry CH2Cl2 (5 ml) was added dropwise, under inert atmosphere at 0 °C, until the addition was complete.The reaction was allowed to stir at room temperature for an additional 3 h, or until complete disappearance of starting materials by TLC. Solvent was removed under reduced pressure and the residue was purified by column chromatography using hexane and ethyl acetate to yield 3a as an off-white solid. Yield: 2.64 g (95percent).

With carbon tetrabromide, triphenylphosphine in dichloromethane, Time= 3h, T= 0 - 20 °C , Inert atmosphere Do, Quang T.; Nguyen, Giang T.; Celis, Victor; Phillips, Robert S.; Archives of Biochemistry and Biophysics; vol.

560; (2014); p. 20 - 26 View in Reaxys

88 %

15.2 :Step 2: Preparation of 3-(2-bromoethyl)-indole (compound of formula 3) 2-(indol-3-yl)ethanol (623mg, 3.86mmol) was dissolved in dichloromethane (20mL) and the solution was cooled to 0. Triphenylphosphine (1.12g, 4.25mmol) and tetrabromomethane (1.41g, 4.25mmol) were then added thereto, followed by stirring for 1 hour. After the reaction was completed, the reaction mixture was concentrated under reduced pressure to remove the solvent.

The resulting residue was purified by column chromatography to afford the title compound (765mg, 88percent).1H NMR (CDCl3, 400MHz): δ 8.10-7.88 (bs, 1H), 7.58 (d, J =8Hz, 1H), 7.38-7.34 (m, 1H), 7.24-7.20 (m, 1H), 7.19-7.08 (m, 2H), 3.65-3.60 (m, 2H), 3.35-3.30 (m, 2H).

With carbon tetrabromide, triphenylphosphine in dichloromethane, Time= 1h, T= 0 °C Patent; DONG-A PHARM.CO., LTD.; KIM, Soon-Hoe; IM, Weon-Bin; CHOI, Sung-Hak; CHOI, Sun-Ho; SOHN, Ju-Hee; SUNG, Hyun-Jung; KIM, Mi-Yeon; CHO, Kang-Hun; SOHN, Tae-Kyoung; WO2011/132901; (2011); (A2) English View in Reaxys

82 %

With NBS, triphenylphosphine in dichloromethane, Time= 1h Yang, Jun; Song, Hao; Xiao, Xue; Wang, Jue; Qin, Yong; Organic Letters; vol. 8; nb. 10; (2006); p. 2187 - 2190 View in Reaxys

67 %

With NBS in tetrachloromethane, Time= 1h, Inert atmosphere, Reflux Dethe, Dattatraya H.; Erande, Rohan D.; Ranjan, Alok; Journal of Organic Chemistry; vol. 78; nb. 20; (2013); p.

10106 - 10120 View in Reaxys

56 %

With phosphorus tribromide in dichloromethane, Time= 2h, T= 0 °C Bowman, W. Russell; Elsegood, Mark R. J.; Stein, Tobias; Weaver, George W.; Organic and Biomolecular Chemistry; vol. 5; nb. 1; (2007); p. 103 - 113 View in Reaxys With diethyl ether, phosphorus tribromide Hoshino; Shimodaira; Justus Liebigs Annalen der Chemie; vol. 520; (1935); p. 19,26 View in Reaxys

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With carbon tetrabromide, triphenylphosphine in dichloromethane, Time= 16h, T= 20 °C Dounay, Amy B.; Barta, Nancy S.; Bikker, Jack A.; Borosky, Susan A.; Campbell, Brian M.; Crawford, Terry; Denny, Lynne; Evans, Lori M.; Gray, David L.; Lee, Pil; Lenoir, Edward A.; Xu, Wenjian; Bioorganic and Medicinal Chemistry Letters; vol. 19; nb. 4; (2009); p. 1159 - 1163 View in Reaxys With phosphorus tribromide in diethyl ether, T= 20 °C Oisaki, Kounosuke; Abe, Junpei; Kanai, Motomu; Organic and Biomolecular Chemistry; vol. 11; nb. 28; (2013); p. 4569 - 4572 View in Reaxys With carbon tetrabromide, triphenylphosphine in acetonitrile, T= 20 °C Liu, Xin; Wang, Songlin; Chen, Yin; Liu, Xinghua; Xu, Xiangqing; Liu, Bi-Feng; Zhang, Guisen; Archiv der Pharmazie; vol. 347; nb. 1; (2014); p. 32 - 41 View in Reaxys OH NH

NH

N

OH

Br

Rx-ID: 25130469 View in Reaxys 2/6 Yield

Conditions & References 4 : PREPARATION 4 PREPARATION 4 To a mechanically stirred mixture of 31 g triphenylphosphine and 375 ml acetonitrile, 18.9 g bromine is added dropwise over 20 minutes.

The mixture is stirred 20 minutes at 0° and the ice bath is removed.

A solution of 17 g of (2-hydroxyethyl)indole in 150 ml acetonitrile is added over 30 minutes.

After stirring 2 hours at room temperature the mixture is diluted with 1000 ml diethyl ether.

The liquid is decanted from the precipitated orange oil.

The residue is washed with an additional 500 ml diethyl ether.

The volume of the ethereal extracts is reduced to about 60 ml and the solution is filtered through 150 g silica gel with diethyl ether.

The solvent is removed to yield 3-(2-bromoethyl)indole, 22.5 g, white waxy solid, mp 57°-60°.

Similarly, proceeding as above, substituting the appropriate hydroxyethylindole for 3-(2-hydroxyethyl)indole, the following compounds are prepared: With bromine, triphenylphosphine in acetonitrile Patent; Syntex (U.S.A.) Inc.; US4332804; (1982); (A1) English View in Reaxys

Br

N O

NH

O

Br

Rx-ID: 40957413 View in Reaxys 3/6 Yield 64 %

Conditions & References With hydrogenchloride, titanium(III) chloride in water, acetonitrile, Time= 4h, T= 20 °C , Inert atmosphere Tong, Shuo; Xu, Zhengren; Mamboury, Mathias; Wang, Qian; Zhu, Jieping; Angewandte Chemie - International Edition; vol. 54; nb. 40; (2015); p. 11809 - 11812; Angew. Chem.; vol. 127; nb. 40; (2015); p. 11975 - 11978,4 View in Reaxys

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NH HN H 2N

Br

Rx-ID: 35784233 View in Reaxys 4/6 Yield

Conditions & References Reaction Steps: 2 1: acetic acid / water / |Reflux 2: phosphorus tribromide / diethyl ether / 20 °C With phosphorus tribromide, acetic acid in diethyl ether, water Oisaki, Kounosuke; Abe, Junpei; Kanai, Motomu; Organic and Biomolecular Chemistry; vol. 11; nb. 28; (2013); p. 4569 - 4572 View in Reaxys

NH

OH N

O

O

Br

Rx-ID: 40957480 View in Reaxys 5/6 Yield

Conditions & References Reaction Steps: 2 1: triphenylphosphine; carbon tetrabromide / dichloromethane / 2 h / 20 °C / |Inert atmosphere 2: titanium(III) chloride; hydrogenchloride / water; acetonitrile / 4 h / 20 °C / |Inert atmosphere With hydrogenchloride, titanium(III) chloride, carbon tetrabromide, triphenylphosphine in dichloromethane, water, acetonitrile Tong, Shuo; Xu, Zhengren; Mamboury, Mathias; Wang, Qian; Zhu, Jieping; Angewandte Chemie - International Edition; vol. 54; nb. 40; (2015); p. 11809 - 11812; Angew. Chem.; vol. 127; nb. 40; (2015); p. 11975 - 11978,4 View in Reaxys

NH

Br

Rx-ID: 5427851 View in Reaxys 6/6 Yield

Conditions & References Jirkovsky,I. et al.; Journal of Heterocyclic Chemistry; vol. 12; (1975); p. 937 - 940 View in Reaxys Najer et al.; Bulletin de la Societe Chimique de France; (1963); p. 2831,2837 View in Reaxys Wenkert et al.; Journal of the American Chemical Society; vol. 84; (1962); p. 3732,3734 View in Reaxys Eryshev et al.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 10; (1974); p. 1313; Khimiya Geterotsiklicheskikh Soedinenii; vol. 10; (1974); p. 1493 View in Reaxys

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