Query Query
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Date
25 reactions in Reaxys
2016-06-23 19h:58m:29s (EST)
25 reactions in Reaxys
2016-06-23 20h:01m:50s (EST)
NH 2
1. Query NH
Search as: As drawn, No mixtures, No charges, No radicals 2. Query
(1. Query) AND NOT itemno in (7)
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NH 2
NH 2 N O
O NH
Rx-ID: 39059040 View in Reaxys 1/25 Yield
Conditions & References
75 %
Anisole (0.95 mL, 8.7 mmol) and R-N-Boc-2-amino-1-(3’-indolyl)butane (2.38 g, 8.2 mmol) were treated with 25 percent TFA/DCM (85 mL) and stirred 18 h at room temperature. The reaction mixture was concentrated and the residue was taken up into ethyl acetate. The organics were washed with 2 N NaOH, water and brine, dried (MgSO4) and concentrated. The crude material was purified by automated flash chromatography (silica gel, 10percent MeOH/ DCM) to yield 1.16 g (75percent) of yellow oil. This material was dissolved into diethyl ether (150 mL) and a solution of fumaric acid (0.25 g, (2.15 mmol) in MeOH (3 mL) was slowly added. The reaction stirred 18 h at room temperature and the solid product was filtered and recrystallized from MeOH/ethyl acetate to yield 211 mg (14percent) of ((+)-7d as a white solid With methoxybenzene, trifluoroacetic acid in dichloromethane, Time= 18h, T= 20 °C Blough, Bruce E.; Landavazo, Antonio; Decker, Ann M.; Page, Kevin M.; Partilla, John S.; Baumann, Michael H.; Rothman, Richard B.; Bioorg. Med. Chem. Lett.; vol. 24; nb. 19; (2014); p. 4754 - 4758 View in Reaxys
NH 2
O HO
E
O 0.5HO
OH
O
E
NH 2 OH N H
O
NH
Rx-ID: 39059056 View in Reaxys 2/25 Yield
Conditions & References
79 %
(R)-2-amino-1-(3’-indolyl)butane (0.5 fumarate) ((+)-7d): General procedure: Anisole (0.95 mL, 8.7 mmol) and R-N-Boc-2-amino-1-(3’-indolyl)butane (2.38 g, 8.2 mmol) were treated with 25 percent TFA/DCM (85 mL) and stirred 18 h at room temperature. The reaction mixture was concentrated and the residue was taken up into ethyl acetate. The organics were washed with 2 N NaOH, water and brine, dried (MgSO4) and concentrated. The crude material was purified by automated flash chromatography (silica gel, 10percent MeOH/DCM) to yield 1.16 g (75percent) of yellow oil. This material was dissolved into diethyl ether (150 mL) and a solution of fumaric acid (0.25 g, (2.15 mmol) in MeOH (3 mL) was slowly added. The reaction stirred 18 h at room temperature and the solid product was filtered and recrystallized from MeOH/ethyl acetate to yield 211 mg (14percent) of ((+)-7d as a white solid, in methanol, diethyl ether, Time= 18h, T= 20 °C Blough, Bruce E.; Landavazo, Antonio; Decker, Ann M.; Page, Kevin M.; Partilla, John S.; Baumann, Michael H.; Rothman, Richard B.; Bioorg. Med. Chem. Lett.; vol. 24; nb. 19; (2014); p. 4754 - 4758 View in Reaxys
NH
NH NH 2 Cl
N O
H
O
Rx-ID: 23072543 View in Reaxys 3/25 Yield
Conditions & References 20.A : PREPARATION OF ETHYL 2-ETHYL-3-PIPERONYLOYL-1,2,3,6-TETRAHYDROAZE-PINO[4,5-B]INDOLE-5-CARBOXYLATE A.
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A solution of 3-(2'-ethyl-2'-nitrovinyl)indole (2.5 g, 11.5 mmol, prepared according to the literature procedure: Young (1958) J. Chem. Soc.:3493-3496) in ethanol was hydrogenated at 40 psi hydrogen in the presence of 10percent Pd/C (0.5 g) for 16 h. Catalyst was removed by filtration and washed with ethanol. Solvent was removed and the crude was dissolved in ethanol (5 mL). The solution was acidified with aqueous HCl (1 N, 30 mL). The solution was extracted with toluene (3*50 mL). The aqueous layer was concentrated under high vacuum to give 2-ethyltryptamine hydrochloride (0.74 g), which was used without further purification. With hydrogen in palladium monocarbide, ethanol Patent; Busch, Brett; Flatt, Brenton T.; Gu, Xiao-Hui; Martin, Richard; Mohan, Raju; Wang, Tie-Lin; Wu, Jason H.; US2005/54634; (2005); (A1) English View in Reaxys 20.A : EXAMPLE 20; PREPARATION OF ETHYL 2-ETHYL-3-PIPERONYLOYL-1,2,3,6-TETRAHYDROAZEPINO[4,5-B]INDOLE-5-CARBOXYLATE A. A solution of 3- (2'-ethyl-2'-nitrovinyl) indole (2.5 g, 11.5 mmol, prepared according to the literature procedure: Young (1958) J. Chem. Soc.: 3493- 3496) in ethanol was hydrogenated at 40 psi hydrogen in the presence of 10percent Pd/C (0.5 g) for 16 h. Catalyst was removed by filtration and washed with ethanol. Solvent was removed and the crude was dissolved in ethanol (5 mL). The solution was acidified with aqueous HCI (1 N, 30 mL). The solution was extracted with toluene (3x50 mL). The aqueous layer was concentrated under high vacuum to give 2- ethyltryptamine hydrochloride (0.74 g), which was used without further purification. Stage 1: With hydrogen, palladium 10 on activated carbon in ethanol, Time= 16h Stage 2: With hydrochlorid acid in ethanol, water Patent; X-CEPTOR THERAPEUTICS, INC.; WO2003/99821; (2003); (A1) English View in Reaxys
NH 2
NH 2 N O
O NH
Rx-ID: 39059039 View in Reaxys 4/25 Yield
Conditions & References General procedure: Anisole (0.95 mL, 8.7 mmol) and R-N-Boc-2-amino-1-(3’-indolyl)butane (2.38 g, 8.2 mmol) were treated with 25 percent TFA/DCM (85 mL) and stirred 18 h at room temperature. The reaction mixture was concentrated and the residue was taken up into ethyl acetate. The organics were washed with 2 N NaOH, water and brine, dried (MgSO4) and concentrated. The crude material was purified by automated flash chromatography (silica gel, 10percent MeOH/DCM) to yield 1.16 g (75percent) of yellow oil. This material was dissolved into diethyl ether (150 mL) and a solution of fumaric acid (0.25 g, (2.15 mmol) in MeOH (3 mL) was slowly added. The reaction stirred 18 h at room temperature and the solid product was filtered and recrystallized from MeOH/ethyl acetate to yield 211 mg (14percent) of ((+)-7d as a white solid With methoxybenzene, trifluoroacetic acid in dichloromethane, Time= 18h, T= 20 °C Blough, Bruce E.; Landavazo, Antonio; Decker, Ann M.; Page, Kevin M.; Partilla, John S.; Baumann, Michael H.; Rothman, Richard B.; Bioorg. Med. Chem. Lett.; vol. 24; nb. 19; (2014); p. 4754 - 4758 View in Reaxys
NH
NH
NH 2
N O
O
Rx-ID: 10344829 View in Reaxys 5/25
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Yield
Conditions & References With chloro-trimethyl-silane, borane in tetrahydrofuran, Time= 14h, T= 20 °C Marshall, Daniel R.; Rodriguez, Gus; Thomson, David S.; Nelson, Richard; Capolina, Allison; Bioorganic and Medicinal Chemistry Letters; vol. 17; nb. 2; (2007); p. 315 - 319 View in Reaxys General procedure: 1-(5’-Chloroindolyl)-2-nitro-1-butene (0.72 g, 2.8 mmol) was dissolved into anhydrous THF (9 mL). A solution of lithium aluminum hydride (1.0 M/THF, 9 mL, 9 mmol) was added slowly and the reaction was refluxed for 18 h. Upon cooling to room temperature, the reaction mixture was quenched with 1/1 water/THF and then basified to pH 0f 9 with 3.0 N aqueous NaOH solution. The mixture was filtered through Celite and the filtrate was concentrated to 0.73 g of brown oil. The crude material was purified by automated flash chromatography (silica gel, 20percent MeOH/DCM) to yield 0.3 g (47 percent) of colorless oil. This material was dissolved into diethyl ether (25 mL) and a solution of fumaric acid (0.17 g, (1.46 mmol) in MeOH (4 mL) was slowly added. The reaction stirred 18 h at room temperature and the solid product was filtered and recrystallized from MeOH/ethyl ether to yield 180 mg (45percent) of 7e as a white solid; With lithium aluminium tetrahydride in tetrahydrofuran, Time= 18h, Reflux Blough, Bruce E.; Landavazo, Antonio; Decker, Ann M.; Page, Kevin M.; Partilla, John S.; Baumann, Michael H.; Rothman, Richard B.; Bioorg. Med. Chem. Lett.; vol. 24; nb. 19; (2014); p. 4754 - 4758 View in Reaxys
NH 2
O HO
E
O 0.5HO
OH
O
E
NH 2 OH N H
O
NH
Rx-ID: 39059057 View in Reaxys 6/25 Yield
Conditions & References
14 %
(R)-2-amino-1-(3’-indolyl)butane (0.5 fumarate) ((+)-7d): Anisole (0.95 mL, 8.7 mmol) and R-N-Boc-2-amino-1-(3’-indolyl)butane (2.38 g, 8.2 mmol) were treated with 25 percent TFA/DCM (85 mL) and stirred 18 h at room temperature. The reaction mixture was concentrated and the residue was taken up into ethyl acetate. The organics were washed with 2 N NaOH, water and brine, dried (MgSO4) and concentrated. The crude material was purified by automated flash chromatography (silica gel, 10percent MeOH/ DCM) to yield 1.16 g (75percent) of yellow oil. This material was dissolved into diethyl ether (150 mL) and a solution of fumaric acid (0.25 g, (2.15 mmol) in MeOH (3 mL) was slowly added. The reaction stirred 18 h at room temperature and the solid product was filtered and recrystallized from MeOH/ethyl acetate to yield 211 mg (14percent) of ((+)-7d as a white solid, mp = 153-155 C;1H NMR (CD3OD 300 MHz)7.36 (d, 1 H, J = 13.2 Hz), 7.14 (d, 2 H, J = 8.1 Hz), 6.95 (s, 1 H), 6.92-6.90 (m, 1 H), 6.87-6.79 (m, 1 H), 6.44 (s, 1 H), 3.20-3.15 (m, 1 H), 2.88-2.86 (m, 1 H), 2.79-2.77 (m, 1 H), 1.53-1.42 (m, 2 H), 0.87 (t, 3 H, J = 7.5 Hz); ESI-MS, calculated for C12H16N2(M+H)+189.3; observed 189.2; Anal. Calculated for C14H18N2O2: C, 68.27; H, 7.37; N, 11.37. Found: C, 67.94; H, 7.36; N, 11.11. in methanol, diethyl ether, Time= 18h, T= 20 °C Blough, Bruce E.; Landavazo, Antonio; Decker, Ann M.; Page, Kevin M.; Partilla, John S.; Baumann, Michael H.; Rothman, Richard B.; Bioorg. Med. Chem. Lett.; vol. 24; nb. 19; (2014); p. 4754 - 4758 View in Reaxys
NH
O
O HO
E
NH 2
O
OH
0.5HO
E
NH 2 OH N H
O
Rx-ID: 39059053 View in Reaxys 7/25 Yield
Conditions & References Preparation of2-Amino-1-(5’-Chloro-(3-Indolyl))butane (0.5 fumarate) (7e). General procedure: 1-(5’-Chloroindolyl)-2-nitro-1-butene (0.72 g, 2.8 mmol) was dissolved into anhydrous THF (9 mL). A solution of lithium aluminum hydride (1.0 M/THF, 9 mL, 9 mmol) was added slowly and the reaction was re-
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fluxed for 18 h. Upon cooling to room temperature, the reaction mixture was quenched with 1/1 water/THF and then basified to pH 0f 9 with 3.0 N aqueous NaOH solution. The mixture was filtered through Celite and the filtrate was concentrated to 0.73 g of brown oil. The crude material was purified by automated flash chromatography (silica gel, 20percent MeOH/DCM) to yield 0.3 g (47 percent) of colorless oil. This material was dissolved into diethyl ether (25 mL) and a solution of fumaric acid (0.17 g, (1.46 mmol) in MeOH (4 mL) was slowly added. The reaction stirred 18 h at room temperature and the solid product was filtered and recrystallized from MeOH/ethyl ether to yield 180 mg (45percent) of 7e as a white solid; in methanol, diethyl ether, Time= 18h, T= 20 °C Blough, Bruce E.; Landavazo, Antonio; Decker, Ann M.; Page, Kevin M.; Partilla, John S.; Baumann, Michael H.; Rothman, Richard B.; Bioorg. Med. Chem. Lett.; vol. 24; nb. 19; (2014); p. 4754 - 4758 View in Reaxys
NH
NH
NH 2
N O
O
Rx-ID: 11133974 View in Reaxys 8/25 Yield
Conditions & References
94 %
With samarium diiodide, water, isopropylamine in tetrahydrofuran Ankner, Tobias; Hilmersson, Goeran; Tetrahedron Letters; vol. 48; nb. 32; (2007); p. 5707 - 5710 View in Reaxys
NH
(+-)-3-<2-nitro-butyl>-indole
NH 2
Rx-ID: 5443664 View in Reaxys 9/25 Yield
Conditions & References With ethanol, nickel, Hydrieren an Platin Snyder; Katz; Journal of the American Chemical Society; vol. 69; (1947); p. 3140 View in Reaxys
NH
NH
NH 2
O
Rx-ID: 12000579 View in Reaxys 10/25 Yield
Conditions & References Reaction Steps: 2 1: AcOH / 4 h / 20 °C / sonication 2: BH3; TMSCl / tetrahydrofuran / 14 h / 20 °C With chloro-trimethyl-silane, borane, acetic acid in tetrahydrofuran Marshall, Daniel R.; Rodriguez, Gus; Thomson, David S.; Nelson, Richard; Capolina, Allison; Bioorganic and Medicinal Chemistry Letters; vol. 17; nb. 2; (2007); p. 315 - 319 View in Reaxys Reaction Steps: 2 1: ammonium acetate / 18 h / |Reflux 2: lithium aluminium tetrahydride / tetrahydrofuran / 18 h / |Reflux With lithium aluminium tetrahydride, ammonium acetate in tetrahydrofuran
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Blough, Bruce E.; Landavazo, Antonio; Decker, Ann M.; Page, Kevin M.; Partilla, John S.; Baumann, Michael H.; Rothman, Richard B.; Bioorg. Med. Chem. Lett.; vol. 24; nb. 19; (2014); p. 4754 - 4758 View in Reaxys
N N
NH 2
N
N O
O
NH
Rx-ID: 39059036 View in Reaxys 11/25 Yield
Conditions & References Reaction Steps: 2 1: palladium 10 on activated carbon; hydrogen / methanol / 18 h / 20 °C 2: methoxybenzene; trifluoroacetic acid / dichloromethane / 18 h / 20 °C With palladium 10 on activated carbon, hydrogen, methoxybenzene, trifluoroacetic acid in methanol, dichloromethane Blough, Bruce E.; Landavazo, Antonio; Decker, Ann M.; Page, Kevin M.; Partilla, John S.; Baumann, Michael H.; Rothman, Richard B.; Bioorg. Med. Chem. Lett.; vol. 24; nb. 19; (2014); p. 4754 - 4758 View in Reaxys
N N
NH 2
N
N O
O
NH
Rx-ID: 39059038 View in Reaxys 12/25 Yield
Conditions & References Reaction Steps: 2 1: palladium 10 on activated carbon; hydrogen / methanol / 18 h / 20 °C 2: methoxybenzene; trifluoroacetic acid / dichloromethane / 18 h / 20 °C With palladium 10 on activated carbon, hydrogen, methoxybenzene, trifluoroacetic acid in methanol, dichloromethane Blough, Bruce E.; Landavazo, Antonio; Decker, Ann M.; Page, Kevin M.; Partilla, John S.; Baumann, Michael H.; Rothman, Richard B.; Bioorg. Med. Chem. Lett.; vol. 24; nb. 19; (2014); p. 4754 - 4758 View in Reaxys
NH
NH NH 2
Rx-ID: 39059102 View in Reaxys 13/25 Yield
Conditions & References Reaction Steps: 3 1.1: trichlorophosphate / 0.17 h / 20 °C 1.2: 1.25 h / 20 °C 1.3: 0.13 h / 100 °C 2.1: ammonium acetate / 18 h / |Reflux 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 18 h / |Reflux With lithium aluminium tetrahydride, ammonium acetate, trichlorophosphate in tetrahydrofuran
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Blough, Bruce E.; Landavazo, Antonio; Decker, Ann M.; Page, Kevin M.; Partilla, John S.; Baumann, Michael H.; Rothman, Richard B.; Bioorg. Med. Chem. Lett.; vol. 24; nb. 19; (2014); p. 4754 - 4758 View in Reaxys
NH 2
NH
NH
Rx-ID: 39059103 View in Reaxys 14/25 Yield
Conditions & References Reaction Steps: 7 1.1: 4-(N,N-dimethlyamino)pyridine / acetonitrile / 18 h / 20 °C / |Inert atmosphere 2.1: N-bromosuccinmide / tetrahydrofuran / 18 h / 20 °C 3.1: n-butyllithium / tetrahydrofuran; hexane / 0.17 h / -78 °C 3.2: 1 h / -78 °C 4.1: pyridine / 18 h / 20 °C / |Cooling with ice 5.1: sodium azide / N,N-dimethyl-formamide / 18 h / 20 °C 6.1: palladium 10 on activated carbon; hydrogen / methanol / 18 h / 20 °C 7.1: methoxybenzene; trifluoroacetic acid / dichloromethane / 18 h / 20 °C With pyridine, 4-(N,N-dimethlyamino)pyridine, N-bromosuccinmide, n-butyllithium, sodium azide, palladium 10 on activated carbon, hydrogen, methoxybenzene, trifluoroacetic acid in tetrahydrofuran, methanol, hexane, dichloromethane, N,N-dimethyl-formamide, acetonitrile Blough, Bruce E.; Landavazo, Antonio; Decker, Ann M.; Page, Kevin M.; Partilla, John S.; Baumann, Michael H.; Rothman, Richard B.; Bioorg. Med. Chem. Lett.; vol. 24; nb. 19; (2014); p. 4754 - 4758 View in Reaxys
NH 2
NH
NH
Rx-ID: 39059104 View in Reaxys 15/25 Yield
Conditions & References Reaction Steps: 7 1.1: 4-(N,N-dimethlyamino)pyridine / acetonitrile / 18 h / 20 °C / |Inert atmosphere 2.1: N-bromosuccinmide / tetrahydrofuran / 18 h / 20 °C 3.1: n-butyllithium / tetrahydrofuran; hexane / 0.17 h / -78 °C 3.2: 1 h / -78 °C 4.1: pyridine / 18 h / 20 °C / |Cooling with ice 5.1: sodium azide / N,N-dimethyl-formamide / 18 h / 20 °C 6.1: palladium 10 on activated carbon; hydrogen / methanol / 18 h / 20 °C 7.1: methoxybenzene; trifluoroacetic acid / dichloromethane / 18 h / 20 °C With pyridine, 4-(N,N-dimethlyamino)pyridine, N-bromosuccinmide, n-butyllithium, sodium azide, palladium 10 on activated carbon, hydrogen, methoxybenzene, trifluoroacetic acid in tetrahydrofuran, methanol, hexane, dichloromethane, N,N-dimethyl-formamide, acetonitrile Blough, Bruce E.; Landavazo, Antonio; Decker, Ann M.; Page, Kevin M.; Partilla, John S.; Baumann, Michael H.; Rothman, Richard B.; Bioorg. Med. Chem. Lett.; vol. 24; nb. 19; (2014); p. 4754 - 4758 View in Reaxys
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NH 2
OH
N O
O NH
Rx-ID: 39059127 View in Reaxys 16/25 Yield
Conditions & References Reaction Steps: 4 1: pyridine / 18 h / 20 °C / |Cooling with ice 2: sodium azide / N,N-dimethyl-formamide / 18 h / 20 °C 3: palladium 10 on activated carbon; hydrogen / methanol / 18 h / 20 °C 4: methoxybenzene; trifluoroacetic acid / dichloromethane / 18 h / 20 °C With pyridine, sodium azide, palladium 10 on activated carbon, hydrogen, methoxybenzene, trifluoroacetic acid in methanol, dichloromethane, N,N-dimethyl-formamide Blough, Bruce E.; Landavazo, Antonio; Decker, Ann M.; Page, Kevin M.; Partilla, John S.; Baumann, Michael H.; Rothman, Richard B.; Bioorg. Med. Chem. Lett.; vol. 24; nb. 19; (2014); p. 4754 - 4758 View in Reaxys
NH 2
OH
N O
O NH
Rx-ID: 39059130 View in Reaxys 17/25 Yield
Conditions & References Reaction Steps: 4 1: pyridine / 18 h / 20 °C / |Cooling with ice 2: sodium azide / N,N-dimethyl-formamide / 18 h / 20 °C 3: palladium 10 on activated carbon; hydrogen / methanol / 18 h / 20 °C 4: methoxybenzene; trifluoroacetic acid / dichloromethane / 18 h / 20 °C With pyridine, sodium azide, palladium 10 on activated carbon, hydrogen, methoxybenzene, trifluoroacetic acid in methanol, dichloromethane, N,N-dimethyl-formamide Blough, Bruce E.; Landavazo, Antonio; Decker, Ann M.; Page, Kevin M.; Partilla, John S.; Baumann, Michael H.; Rothman, Richard B.; Bioorg. Med. Chem. Lett.; vol. 24; nb. 19; (2014); p. 4754 - 4758 View in Reaxys
NH 2
O O N NH
Rx-ID: 39059135 View in Reaxys 18/25 Yield
Conditions & References Reaction Steps: 6 1.1: N-bromosuccinmide / tetrahydrofuran / 18 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 0.17 h / -78 °C 2.2: 1 h / -78 °C 3.1: pyridine / 18 h / 20 °C / |Cooling with ice 4.1: sodium azide / N,N-dimethyl-formamide / 18 h / 20 °C 5.1: palladium 10 on activated carbon; hydrogen / methanol / 18 h / 20 °C 6.1: methoxybenzene; trifluoroacetic acid / dichloromethane / 18 h / 20 °C With pyridine, N-bromosuccinmide, n-butyllithium, sodium azide, palladium 10 on activated carbon, hydrogen, methoxybenzene, trifluoroacetic acid in tetrahydrofuran, methanol, hexane, dichloromethane, N,N-dimethyl-formamide
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Blough, Bruce E.; Landavazo, Antonio; Decker, Ann M.; Page, Kevin M.; Partilla, John S.; Baumann, Michael H.; Rothman, Richard B.; Bioorg. Med. Chem. Lett.; vol. 24; nb. 19; (2014); p. 4754 - 4758 View in Reaxys
NH 2
O O N NH
Rx-ID: 39059136 View in Reaxys 19/25 Yield
Conditions & References Reaction Steps: 6 1.1: N-bromosuccinmide / tetrahydrofuran / 18 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 0.17 h / -78 °C 2.2: 1 h / -78 °C 3.1: pyridine / 18 h / 20 °C / |Cooling with ice 4.1: sodium azide / N,N-dimethyl-formamide / 18 h / 20 °C 5.1: palladium 10 on activated carbon; hydrogen / methanol / 18 h / 20 °C 6.1: methoxybenzene; trifluoroacetic acid / dichloromethane / 18 h / 20 °C With pyridine, N-bromosuccinmide, n-butyllithium, sodium azide, palladium 10 on activated carbon, hydrogen, methoxybenzene, trifluoroacetic acid in tetrahydrofuran, methanol, hexane, dichloromethane, N,N-dimethyl-formamide Blough, Bruce E.; Landavazo, Antonio; Decker, Ann M.; Page, Kevin M.; Partilla, John S.; Baumann, Michael H.; Rothman, Richard B.; Bioorg. Med. Chem. Lett.; vol. 24; nb. 19; (2014); p. 4754 - 4758 View in Reaxys
Br
NH 2
O N O NH
Rx-ID: 39059145 View in Reaxys 20/25 Yield
Conditions & References Reaction Steps: 5 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.17 h / -78 °C 1.2: 1 h / -78 °C 2.1: pyridine / 18 h / 20 °C / |Cooling with ice 3.1: sodium azide / N,N-dimethyl-formamide / 18 h / 20 °C 4.1: palladium 10 on activated carbon; hydrogen / methanol / 18 h / 20 °C 5.1: methoxybenzene; trifluoroacetic acid / dichloromethane / 18 h / 20 °C With pyridine, n-butyllithium, sodium azide, palladium 10 on activated carbon, hydrogen, methoxybenzene, trifluoroacetic acid in tetrahydrofuran, methanol, hexane, dichloromethane, N,N-dimethyl-formamide Blough, Bruce E.; Landavazo, Antonio; Decker, Ann M.; Page, Kevin M.; Partilla, John S.; Baumann, Michael H.; Rothman, Richard B.; Bioorg. Med. Chem. Lett.; vol. 24; nb. 19; (2014); p. 4754 - 4758 View in Reaxys
Br
NH 2
O N O NH
Rx-ID: 39059146 View in Reaxys 21/25 Yield
Conditions & References Reaction Steps: 5 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.17 h / -78 °C 1.2: 1 h / -78 °C
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2.1: pyridine / 18 h / 20 °C / |Cooling with ice 3.1: sodium azide / N,N-dimethyl-formamide / 18 h / 20 °C 4.1: palladium 10 on activated carbon; hydrogen / methanol / 18 h / 20 °C 5.1: methoxybenzene; trifluoroacetic acid / dichloromethane / 18 h / 20 °C With pyridine, n-butyllithium, sodium azide, palladium 10 on activated carbon, hydrogen, methoxybenzene, trifluoroacetic acid in tetrahydrofuran, methanol, hexane, dichloromethane, N,N-dimethyl-formamide Blough, Bruce E.; Landavazo, Antonio; Decker, Ann M.; Page, Kevin M.; Partilla, John S.; Baumann, Michael H.; Rothman, Richard B.; Bioorg. Med. Chem. Lett.; vol. 24; nb. 19; (2014); p. 4754 - 4758 View in Reaxys
NH 2
O
S
O
O
NH
N O
O
Rx-ID: 39059151 View in Reaxys 22/25 Yield
Conditions & References Reaction Steps: 3 1: sodium azide / N,N-dimethyl-formamide / 18 h / 20 °C 2: palladium 10 on activated carbon; hydrogen / methanol / 18 h / 20 °C 3: methoxybenzene; trifluoroacetic acid / dichloromethane / 18 h / 20 °C With sodium azide, palladium 10 on activated carbon, hydrogen, methoxybenzene, trifluoroacetic acid in methanol, dichloromethane, N,N-dimethyl-formamide Blough, Bruce E.; Landavazo, Antonio; Decker, Ann M.; Page, Kevin M.; Partilla, John S.; Baumann, Michael H.; Rothman, Richard B.; Bioorg. Med. Chem. Lett.; vol. 24; nb. 19; (2014); p. 4754 - 4758 View in Reaxys
NH 2
O
S
O
O
NH
N O
O
Rx-ID: 39059154 View in Reaxys 23/25 Yield
Conditions & References Reaction Steps: 3 1: sodium azide / N,N-dimethyl-formamide / 18 h / 20 °C 2: palladium 10 on activated carbon; hydrogen / methanol / 18 h / 20 °C 3: methoxybenzene; trifluoroacetic acid / dichloromethane / 18 h / 20 °C With sodium azide, palladium 10 on activated carbon, hydrogen, methoxybenzene, trifluoroacetic acid in methanol, dichloromethane, N,N-dimethyl-formamide Blough, Bruce E.; Landavazo, Antonio; Decker, Ann M.; Page, Kevin M.; Partilla, John S.; Baumann, Michael H.; Rothman, Richard B.; Bioorg. Med. Chem. Lett.; vol. 24; nb. 19; (2014); p. 4754 - 4758 View in Reaxys
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NH
NH
NH 2
E N O
O
Rx-ID: 265051 View in Reaxys 24/25 Yield
Conditions & References With lithium aluminium tetrahydride, diethyl ether Young; Journal of the Chemical Society; (1958); p. 3493,3494 View in Reaxys
NH
NH 2
Rx-ID: 5443663 View in Reaxys 25/25 Yield
Conditions & References aus I Bulatova et al.; Pharmaceutical Chemistry Journal; nb. 11; (1968); p. 594; Khimiko-Farmatsevticheskii Zhurnal; nb. 11; (1968); p. 6 View in Reaxys 1-<Oxindolyl-(3)>-butanon-(2)-oxim, Na/Propanol-(1) Pietra; Tacconi; Farmaco, Edizione Scientifica; vol. 16; (1961); p. 483,490 View in Reaxys 3-(2-Nitrobutyl)-indol, Hydrierung an Pd-C Patent; Leslie H. Smith and Imperial Chem. Ind. Ltd.; GB935592; (1961); ; vol. 60; nb. 2898g; (1964) View in Reaxys 3-(2-Ethyl-2-nitrovinyl)indol, EtOH/NH3, Hydrierung ueber Pd-C unter Druck Patent; Imperial Chem. Ind. Ltd.; GB933786; (1961); ; vol. 60; nb. 1705a; (1964) View in Reaxys 1-Benzyl-α-ethyl-tryptamin, Na/NH3 Julia et al.; Bulletin de la Societe Chimique de France; (1966); p. 2291,2293 View in Reaxys 3-(2-Azidobutyryl)indol 1h, LiAlH4/THF Bergman,J. et al.; Tetrahedron; vol. 29; (1973); p. 971 - 976 View in Reaxys 1-<Indolyl-(3)>-2-acetamino-butanon-(3), Erhitzen mit. wss. KOH, wss. Hydrazinhydrat, Diethylenglykol auf 195-205grad Heinzelman et al.; Journal of Organic Chemistry; vol. 25; (1960); p. 1548,1552 View in Reaxys α-Ethyl-β-indolenidenium-ethylnitronat, LiAlH4/THF, erhitzen Heinzelman et al.; Journal of Organic Chemistry; vol. 25; (1960); p. 1548,1552 View in Reaxys 9.A : PREPARATION OF N-PROPYL-3(4-FLUOROBENZOYL)-2-ETHYL-1,2,3,6-TETRAHYDROAZEPINO[4,5B]INDOLE-5-CARBOXYLATE A.
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α-Ethyl tryptamine was prepared in a manner similar to that described in Steps A and B of Example 8 by replacing nitroethane with 1-nitropropane at Step A; MS (ESI): 207 (MH+). Patent; Busch, Brett; Flatt, Brenton T.; Gu, Xiao-Hui; Martin, Richard; Mohan, Raju; Wang, Tie-Lin; Wu, Jason H.; US2005/54634; (2005); (A1) English View in Reaxys 9.A Patent; X-CEPTOR THERAPEUTICS, INC.; WO2003/99821; (2003); (A1) English View in Reaxys
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