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Citations (10)
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1
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Rx-ID: 36697875 Find similar reactions
With potassium carbonate in N,N-dimethyl-formamide
T=120°C; 16 h;
2
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Aristotelous, Tonia; Ahn, Seungkirl; Shukla, Arun K.; Gawron, Sylwia; Sassano, Maria F.; Kahsai, Alem W.; Wingler, Laura M.; Zhu, Xiao; Tripathi-Shukla, Prachi; Huang, Xi-Ping; Riley, Jennifer; Besnard, Jeremy; Read, Kevin D.; Roth, Bryan L.; Gilbert, Ian H.; Hopkins, Andrew L.; Lefkowitz, Robert J.; Navratilova, Iva
ACS Medicinal Chemistry Letters, 2013 , vol. 4, # 10 p. 1005 - 1010 Title/Abstract Full Text View citing articles Show Details
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Rx-ID: 23459118 Find similar reactions
ELI LILLY AND COMPANY
Patent: WO2005/66126 A1, 2005 ; Location in patent: Page/Page column 42 ;
60%
Title/Abstract Full Text Show Details
3
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Reflux; Hide Experimental Procedure
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Rx-ID: 30095106 Find similar reactions
Nirogi, Ramakrishna V.S.; Deshpande, Amol D.; Kambhampati, Ramasastri; Badange, Rajesh Kumar; Kota, Laxman; Daulatabad, Anand V.; Shinde, Anil K.; Ahmad, Ishtiyaque; Kandikere, Vishwottam; Jayarajan, Pradeep; Dubey
Bioorganic and Medicinal Chemistry Letters, 2011 , vol. 21, # 1 p. 346 - 349 Title/Abstract Full Text View citing articles Show Details
5-Bromo-3-(4-methylpiperazin-1-yl)-1H-indole (6h) General procedure: Intermediate obtained as above was stirred with 85 percent potassium hydroxide (0.0038 mmole) in ethanol at reflux temperature. The progress of the reaction was monitored by TLC. After completion of the reaction, solvent was removed under pressure. The residual mass was dissolved in 100 mL ethyl acetate and the separated organic layer was washed with brine solution and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the residual mass was purified by flash chromatography over silica gel using ethyl acetate containing 1 percent triethylamine as eluent to obtain the intermediate 5-Bromo-3-(4-methylpiperazin-1-yl)-1H-indole in 90 percent yield.
4
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Reflux;
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Rx-ID: 30095107 Find similar reactions
Nirogi, Ramakrishna V.S.; Deshpande, Amol D.; Kambhampati, Ramasastri; Badange, Rajesh Kumar; Kota, Laxman; Daulatabad, Anand V.; Shinde, Anil K.; Ahmad, Ishtiyaque; Kandikere, Vishwottam; Jayarajan, Pradeep; Dubey
Bioorganic and Medicinal Chemistry Letters, 2011 , vol. 21, # 1 p. 346 - 349
Hide Experimental Procedure
Title/Abstract Full Text View citing articles Show Details
5-Bromo-3-(4-methylpiperazin-1-yl)-1H-indole (6h) General procedure: Intermediate obtained as above was stirred with 85 percent potassium hydroxide (0.0038 mmole) in ethanol at reflux temperature. The progress of the reaction was monitored by TLC. After completion of the reaction, solvent was removed under pressure. The residual mass was dissolved in 100 mL ethyl acetate and the separated organic layer was washed with brine solution and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the residual mass was purified by flash chromatography over silica gel using ethyl acetate containing 1 percent triethylamine as eluent to obtain the intermediate 5-Bromo-3-(4-methylpiperazin-1-yl)-1H-indole in 90 percent yield.
5
Synthesize Find similar resp. N-Acetylindol, NaOH;
Rx-ID: 6095509 Find similar reactions
Lab. Sauba S.A.
Patent: DE2811031 , 1978 ; Chem.Abstr., vol. 90, # 38962 Full Text Show Details
6
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Reflux; Hide Experimental Procedure
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Rx-ID: 30095109 Find similar reactions
Nirogi, Ramakrishna V.S.; Deshpande, Amol D.; Kambhampati, Ramasastri; Badange, Rajesh Kumar; Kota, Laxman; Daulatabad, Anand V.; Shinde, Anil K.; Ahmad, Ishtiyaque; Kandikere, Vishwottam; Jayarajan, Pradeep; Dubey
Bioorganic and Medicinal Chemistry Letters, 2011 , vol. 21, # 1 p. 346 - 349 Title/Abstract Full Text View citing articles Show Details
5-Bromo-3-(4-methylpiperazin-1-yl)-1H-indole (6h) General procedure: Intermediate obtained as above was stirred with 85 percent potassium hydroxide (0.0038 mmole) in ethanol at reflux temperature. The progress of the reaction was monitored by TLC. After completion of the reaction, solvent was removed under pressure. The residual mass was dissolved in 100 mL ethyl acetate and the separated organic layer was washed with brine solution and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the residual mass was purified by flash chromatography over silica gel using ethyl acetate containing 1 percent triethylamine as eluent to obtain the intermediate 5-Bromo-3-(4-methylpiperazin-1-yl)-1H-indole in 90 percent yield.
7
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With potassium hydroxide in ethanol
Reflux; Hide Experimental Procedure
Synthesize Find similar
Rx-ID: 30095108 Find similar reactions
Nirogi, Ramakrishna V.S.; Deshpande, Amol D.; Kambhampati, Ramasastri; Badange, Rajesh Kumar; Kota, Laxman; Daulatabad, Anand V.; Shinde, Anil K.; Ahmad, Ishtiyaque; Kandikere, Vishwottam; Jayarajan, Pradeep; Dubey
Bioorganic and Medicinal Chemistry Letters, 2011 , vol. 21, # 1 p. 346 - 349 Title/Abstract Full Text View citing articles Show Details
5-Bromo-3-(4-methylpiperazin-1-yl)-1H-indole (6h) General procedure: Intermediate obtained as above was stirred with 85 percent potassium hydroxide (0.0038 mmole) in ethanol at reflux temperature. The progress of the reaction was monitored by TLC. After completion of the reaction, solvent was removed under pressure. The residual mass was dissolved in 100 mL ethyl acetate and the separated organic layer was washed with brine solution and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the residual mass was purified by flash chromatography over silica gel using ethyl acetate containing 1 percent triethylamine as eluent to obtain the intermediate 5-Bromo-3-(4-methylpiperazin-1-yl)-1H-indole in 90 percent yield.
8
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With triethylamine in methanol
1 h; Heating / reflux; Hide Experimental Procedure
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Rx-ID: 25916961 Find similar reactions
MEMORY PHARMACEUTICALS CORPORATION
Patent: WO2007/98418 A1, 2007 ; Location in patent: Page/Page column 111-112; 113 ; Title/Abstract Full Text Show Details
5:
Into a 250 mL round bottom flask was placed a solution of tert-butyl 4-(l-acetyl-lH-indol- 3-yl) piperazine-1 -carboxylate (2.6 g, 7.58 mmol) in methanol (80 mL). To the mixture was added Et3N (2.3 g, 22.73 mmol). The resulting solution was allowed to react, with stirring, for 1 hour while the temperature was maintained at reflux in a bath of oil. The reaction progress was monitored by LCMS and TLC (ethyl acetate/petroleum, ether = 1:1). The mixture was concentrated by evaporation under vacuum using a rotary evaporator. The resulting solution was diluted with 200 mL of ethyl acetate. The resulting mixture was washed 3 times with 150 mL of NaCl(aq.). The residue was purified by eluting through a column with a 10:1 petroleum ether/ethyl acetate solvent system. This resulted in 2.1 g (89percent) of tert-butyl 4-(lH-indol-3-yl) piperazine-1 -carboxylate as a light pink solid.1H NMR (400MHz, CDCl3) δ 1.55 (9H, s), 3.1 (4H, s), 3.7
(4H, s), 6.7 (IH, s), 7.21 (IH, t), 7.32 (IH, t), 7.34 (IH, d), 7.68 (IH, d), 7.7 (IH, d). m/z 302 (M++].).
9
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2:
With methanol; potassium hydroxide
Heating / reflux; Hide Experimental Procedure
Synthesize Find similar SUVEN LIFE SCIENCES LIMITED
Patent: WO2007/138611 A1, 2007 ; Location in patent: Page/Page column 19 ; Title/Abstract Full Text Show Details
Rx-ID: 10698892 Find similar reactions
Description 2: 3-(4-Ethylpiperazin-l-yl)-5-bromo indole:; N-Acetyl-3-(4-ethyIpiperazin-l-yI)-5-bromoindole (4.6 g) technical material obtained as above was stirred with methanolic solution of 85 percent potassium hydroxide (2.55 g, 3.87 mM in 46 mL of methanol) at reflux temperature. The progress of reaction was monitored by TLC. After completion of reaction, solvent was removed under vacuum. The residual mass was dissolved in 100 mL ethyl acetate. The organic layer was washed with brine solution and dried over anhydrous magnesium sulfate. Solvent removal under vacuum yielded the desired product (3.7 g, 91 percent yield). Column purification from silica gel, 100 - 200 mesh size using ethyl acetate containing 1 percent triethyl amine as eluent afforded the pure product in 51 percent yield. Mass (m/z): 308.2, 310.2 (M+H)+; 1H-NMR (δ ppm): 1.13 - 1.16 (3H, t, J = 7.20), 2.49 - 2.55 (2H, q, J = 7.24), 2.69 (4H, bs), 3.11 (4H, bs), 6.753 - 6.759 (IH, d, J = 2.44), 7.17 - 7.19 (IH, d, J = 8.6), 7.24 - 7.26 (IH, dd, J = 8.68, 2.0), 7.73 (IH, bs), 7.75 - 7.76 (IH, d, J = 1.6). With potassium hydroxide in ethanol
Reflux; Hide Experimental Procedure
Nirogi, Ramakrishna V.S.; Deshpande, Amol D.; Kambhampati, Ramasastri; Badange, Rajesh Kumar; Kota, Laxman; Daulatabad, Anand V.; Shinde, Anil K.; Ahmad, Ishtiyaque; Kandikere, Vishwottam; Jayarajan, Pradeep; Dubey
Bioorganic and Medicinal Chemistry Letters, 2011 , vol. 21, # 1 p. 346 - 349 Title/Abstract Full Text View citing articles Show Details
5-Bromo-3-(4-methylpiperazin-1-yl)-1H-indole (6h) General procedure: Intermediate obtained as above was stirred with 85 percent potassium hydroxide (0.0038 mmole) in ethanol at reflux temperature. The progress of the reaction was monitored by TLC. After completion of the reaction, solvent was removed under pressure. The residual mass was dissolved in 100 mL ethyl acetate and the separated organic layer was washed with brine solution and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the residual mass was purified by flash chromatography over silica gel using ethyl acetate containing 1 percent triethylamine as eluent to obtain the intermediate 5-Bromo-3-(4-methylpiperazin-1-yl)-1H-indole in 90 percent yield.
10
Synthesize Find similar resp. N-Acetylindol, NaOH;
Rx-ID: 6113895 Find similar reactions
Lab. Sauba S.A.
Patent: DE2811031 , 1978 ; Chem.Abstr., vol. 90, # 38962 Full Text Show Details
11
Synthesize Find similar Chlorhydrat B-2, NaOH;
12
Rx-ID: 6134798 Find similar reactions
Lab. Sauba S.A.
Patent: DE2811031 , 1978 ; Chem.Abstr., vol. 90, # 38962 Full Text Show Details
Synthesize Find similar N-Acetylindol B-1, NaOH;
Rx-ID: 6137648 Find similar reactions
Lab. Sauba S.A.
Patent: DE2811031 , 1978 ; Chem.Abstr., vol. 90, # 38962 Full Text Show Details
13
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Rx-ID: 22993166 Find similar reactions
GLAXO GROUP LIMITED
Patent: WO2004/46124 A1, 2004 ; Location in patent: Page 89 ; Title/Abstract Full Text Show Details
14
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Hide Experimental Procedure
Rx-ID: 25350474 Find similar reactions
SANOFI-SYNTHELABO; Mitsubishi-Tokyo Pharmaceuticals, Inc.
Patent: EP1136483 A1, 2001 ; Title/Abstract Full Text Show Details
Particularly preferred compounds of the present invention represented by formula (I) include: ...
2-[4-(5-trifluoromethylpyridin-2-yl)piperazin-1-yl]-6-pyridin-4-ylpyrimidin-4(1H)-one, 2-[4-(quinolin-2-yl)piperazin-1-yl]-6-pyridin-4-ylpyrimidin-4(1H)-one, 2-[4-(imidazo[1,2-a ]pyridin-5-yl)piperazin-1-yl]-6-pyridin-4-ylpyrimidin-4(1H)-one, 2-[4-(1H -indazol-4-yl)piperazin-1-yl]-6-pyridin-4-ylpyrimidin-4(1H)-one, 2-[4-(5-methoxy-1H -indol-3-yl)piperazin-1-yl]-6-pyridin-4-ylpyrimidin-4(1H)-one, 2-[4-(imidazo[4,5-c ]pyridin-4-yl)piperazin-1-yl]-6-pyridin-4-ylpyrimidin-4(1H)-one, 2-[4-(1H -indazol-7-yl)piperazin-1-yl)-6-pyridin-4-ylpyrimidin-4(1H)-one, 2-[4-(4-methoxy-1H -benzimidazol-7-yl)piperazin-1-yl]-6-pyridin-4-ylpyrimidin-4(1H)-one, ...
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SANOFI-SYNTHELABO; Mitsubishi-Tokyo Pharmaceuticals, Inc.
Patent: EP1136483 A1, 2001 ; Title/Abstract Full Text Show Details
A pyrimidone derivative which is selected from the group consisting of: ... 2-[4-(5-trifluoromethylpyridin-2-yl)piperazin-1-yl]-6-pyridin-4-ylpyrimidin-4(1H)-one, 2-[4-(quinolin-2-yl)piperazin-1-yl]-6-pyridin-4-ylpyrimidin-4(1H)-one, 2-[4-(imidazo[1,2-a ]pyridin-5-yl)piperazin-1-yl]-6-pyridin-4-ylpyrimidin-4(1H)-one, 2-[4-(1H -indazol-4-yl)piperazin-1-yl]-6-pyridin-4-ylpyrimidin-4(1H)-one, 2-[4-(5-methoxy-1H -indol-3-yl)piperazin-1-yl]-6-pyridin-4-ylpyrimidin-4(1H)-one, 2-[4-(imidazo[4,5-c ]pyridin-4-yl)piperazin-1-yl]-6-pyridin-4-ylpyrimidin-4(1H)-one, 2-[4-(1H -indazol-7-yl)piperazin-1-yl]-6-pyridin-4-ylpyrimidin-4(1H)-one, 2-[4-(4-methoxy-1H -benzimidazol-7-yl)piperazin-1-yl]-6-pyridin-4-ylpyrimidin-4(1H)-one, ...
15
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Rx-ID: 22993167 Find similar reactions
GLAXO GROUP LIMITED
Patent: WO2004/46124 A1, 2004 ; Location in patent: Page 89 ;
Title/Abstract Full Text Show Details
16
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With potassium carbonate in tetrahydrofuran; ethanol; water T=25°C; 24 h; Hide Experimental Procedure
Rx-ID: 45146041 Find similar reactions
Guangdong East Sunshine Pharmaceutical Co., Ltd; Jin, Chunfei; Zhong, Wenhe; Zhang, Yingjun
Patent: CN106045966 A, 2016 ; Location in patent: Paragraph 0227; 0228; 0229; 0230; 0254; 0255; 0256-0258 ; Title/Abstract Full Text Show Details
3.5:Step 7) 3- (1 - ((4-methoxy-3- (piperazin-1-yl) phenyl) sulfonyl) piperidin-4-yl) lH-indole bondedto
General procedure: A solution of 1- (4- (5 - ((4- (1H-indol-3-yl) piperidin-1-yl) sulfonyl) -2-methoxyphenyl)piperazine- 1-yl) -2,2,2-trifluoroethanone (900 mg, 1.63 mmol) was dissolved ina mixed solvent of tetrahydrofuran(10 mL), ethanol (10 mL) and water(10 mL) followed by potassium carbonate (662 mg, 4.8 Mmol).After the reaction was stirred for 24 hours,dichloromethane (60 mL) was added, washed with saturated sodium chloride solution (30 mL), and the organic phase was separated and dried over anhydrous sodium sulfate.Filtered,the filtrate by rotary evaporation under reduced pressure, purified by column chromatography (dichloromethane / methanol (v / v) = 20/ 1)to give the title compound as a white solid(690mg, 93percent).
17
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Rx-ID: 31601601 Find similar reactions
Dainippon Sumitomo Pharma Co., Ltd.; MARUYAMA, Megumi; KINOMURA, Naoya; NOJIMA, Satoshi; TAKAMURA, Masahiro; KAKIGUCHI, Keisuke; TATAMITANI, Hiroto
Patent: WO2011/111875 A1, 2011 ; Location in patent: Page/Page column 98; 102 ; Title/Abstract Full Text Show Details