Alternatived Products of [ 76195-80-7 ]
Product Details of [ 76195-80-7 ]
CAS No. : | 76195-80-7 |
MDL No. : | MFCD05181003 |
Formula : |
C16H13NO2
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Boiling Point : |
- |
Linear Structure Formula : | - |
InChI Key : | - |
M.W : |
251.28
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Pubchem ID : | - |
Synonyms : |
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Safety of [ 76195-80-7 ]
Signal Word: | |
Class: | |
Precautionary Statements: | |
UN#: | |
Hazard Statements: | |
Packing Group: | |
Application In Synthesis of [ 76195-80-7 ]
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
- Downstream synthetic route of [ 76195-80-7 ]
- 1
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[ 5784-95-2 ]
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[ 33513-42-7 ]
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[ 76195-80-7 ]
Yield | Reaction Conditions | Operation in experiment |
90% |
|
General procedure: Under nitrogen gas, phosphorous oxychloride (10 mmol) was added dropwise to dry dimethylformamide (DMF) (10 mmol) while cooling in an ice bath, and the reaction mixture was stirred for 1 h. A solution of compound 4 (1 mmol) in DMF (50 ml) was added dropwise to the mixture with continuous stirring, which was then heated to 70 C. The mixture was poured onto ice cold water (200 mL), naturalized with 40% NaOH, and extracted with chloroform. The chloroform extract was washed with water and dried over Na2SO4. The solvent was removed under vacuum. The residue was crystalized from an ethanol/water mixed solvent system. |
90% |
With trichlorophosphate; at 70℃;Inert atmosphere; |
General procedure: Under nitrogen gas, phosphorous oxychloride (10 mmol) was added dropwise to dry dimethylformamide (DMF) (10 mmol) while cooling in an ice bath, and the reaction mixture was stirred for 1 h. A solution of compound 3 (1 mmol) in DMF (50 ml) was added dropwise to the mixture with continuous stirring, which was then heated to 70 C. The mixture was poured onto ice cold water (200 mL), naturalized with 40% NaOH, and extracted with chloroform. The chloroform extract was washed with water and dried over Na2SO4.The solvent was removed under vacuum. The residue was crystalized from an ethanol/water mixed solvent system [27]. |
88% |
With trichlorophosphate; at 10 - 45℃; for 0.5h; |
General procedure: Compounds 10a-f were synthesized by known procedure. A solution of 2-aryl-1H-indole 9a-f (0.01 mol) in a minimum amount of DMF was added to the Vilsmeier-Haack reagent (was prepared from phosphorus oxychloride (1 mL) and DMF(3.15 mL)) maintaining the reaction temperature between 10 and 20 C. The reaction mixture was heated at 45 C for 30 min and poured into a mixture of ice-water (100 mL) and 10% aqueous NaOH (20 mL). The resulting mixture was refl uxed for 1 h and cooled to room temperature. The precipitate was collected by filtration, washed with water, dried, and recrystallized. |
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General procedure: A round-bottomed flask containing (28mL, 370mmol) freshly distilled dimethylformamide (DMF) was cooled to 0C for about 30min and freshly distilled phosphorus oxychloride (8.41mL, 90mmol) was subsequently added with stirring to the DMF over a period of 30min. A solution of indole 19 (85.47mmol) in DMF (10mL, 130mmol) was added to the yellow solution over a period of 1h. The solution was stirred at room temperature till it become a yellow paste. At the end of the reaction, 30g of crushed ice was added to the paste with stirring to make a clear cherry-red aqueous solution. Sodium hydroxide solution (1N, 100mL) was added dropwise with stirring to this cherry-red solution. The resulting suspension was heated rapidly to 90C and allowed to cool at room temperature, after which it was refrigerated for overnight. The product was filtered, washed with water (2×100mL) and air-dried to afford pure indole-3-carboxaldehydes 20 in 80-90% yields. Indole-3-carboxaldehyde, pale yellow solid; mp 194-196C (Lit. [37]196-197C). |
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General procedure: P-substituted acetophenone (2mmol) and phenyl-hydrazine (2mmol) were poured into a round bottom flask, then CH3COOH (0.5mL) and CH4O3S (27mmol) were added. After the thin layer chromatography (TLC) monitoring reaction was completed, the intermediate 3 was obtained by pouring the mixture into ice water. At -30C, POCl3 (10mmol) was slowly added dropwise to a round bottom flask containing DMF (10mmol), and the reaction was stirred for 1h. After that, intermediate 3 (1mmol) was dissolved in DMF, slowly added dropwise to the flask, and the reaction was heated to 70C with stirring. Monitor the reaction through the TLC. Finally, the mixture was poured into ice water, washed with 40% NaOH solution, and then extracted with DCM to obtain intermediate 4. |
Reference:
[1]Research on Chemical Intermediates,2019,vol. 45,p. 2827 - 2854
[2]Chemistry and biodiversity,2019,vol. 16
[3]Research on Chemical Intermediates,2019,vol. 45,p. 5261 - 5290
[4]Russian Chemical Bulletin,2019,vol. 68,p. 2262 - 2270
Izv. Akad. Nauk, Ser. Khim.,2019,p. 2262 - 2270,9
[5]Pharmaceutical Chemistry Journal,1994,vol. 28,p. 751 - 755
Khimiko-Farmatsevticheskii Zhurnal,1994,vol. 28,p. 47 - 50
[6]Journal of Medicinal Chemistry,1998,vol. 41,p. 4965 - 4972
[7]Tetrahedron Letters,2005,vol. 46,p. 377 - 380
[8]Medicinal Chemistry Research,2012,vol. 21,p. 3406 - 3416
[9]European Journal of Medicinal Chemistry,2017,vol. 136,p. 184 - 194
[10]Organic Letters,2019,vol. 21,p. 2602 - 2605
[11]Journal of Heterocyclic Chemistry,2019,vol. 56,p. 3303 - 3312
[12]Bioorganic Chemistry,2020,vol. 99
- 2
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[ 5784-95-2 ]
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[ 100-97-0 ]
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[ 76195-80-7 ]
Yield | Reaction Conditions | Operation in experiment |
78% |
With silica supported ceric ammonium nitrate; In acetonitrile; for 12h;Reflux; |
General procedure: a mixture of indole (1 mmol), HMTA (2.5 mmol), and 10% CAN-SiO2 was refluxed in CH3CN (5.0 mL). After the reaction was complete, the mixture was evaporated to give a crude residue of CAN-SiO2 and product. The crude residue was washed with EtOAc (10 mL 5) and dried to leave a crude product that was purified by short flash column chromatography (EtOAc/hexane = 1:3). |
- 3
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[ 68-12-2 ]
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[ 157869-15-3 ]
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[ 76195-80-7 ]
- 4
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[ 76195-80-7 ]
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[ 51516-70-2 ]
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(E)-1-(4-fluorophenyl)-5-(((2-(4-methoxyphenyl)-1H-indol-3-yl)methylene)amino)-1H-pyrazole-4-carbonitrile
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
With hydrogenchloride; In ethanol; water; at 80℃; |
General procedure: Intermediate 4 (1mmol) and the intermediate 7 (1mmol) were dissolved in ethanol to the glass flask, then HCl solution was added as a catalyst refluxed at 80C for 15-18h. After the TLC monitoring reaction was completed, the mixture was vacuum filtered and concentrated. Finally, the above crude product can be isolated and purified by column chromatography (Hexane/EtOAc=8:1) to obtain target compounds. |
- 5
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[ 76195-80-7 ]
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[ 51516-67-7 ]
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(E)-1-(4-chlorophenyl)-5-(((2-(4-methoxyphenyl)-1H-indol-3-yl)methylene)amino)-1H-pyrazole-4-carbonitrile
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
With hydrogenchloride; In ethanol; water; at 80℃; |
General procedure: Intermediate 4 (1mmol) and the intermediate 7 (1mmol) were dissolved in ethanol to the glass flask, then HCl solution was added as a catalyst refluxed at 80C for 15-18h. After the TLC monitoring reaction was completed, the mixture was vacuum filtered and concentrated. Finally, the above crude product can be isolated and purified by column chromatography (Hexane/EtOAc=8:1) to obtain target compounds. |
- 6
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[ 76195-80-7 ]
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[ 103646-82-8 ]
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(E)-5-(((2-(4-methoxyphenyl)-1H-indol-3-yl)methylene)amino)-1-(p-tolyl)-1H-pyrazole-4-carbonitrile
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
With hydrogenchloride In ethanol; water at 80℃; |
4.1.3 General procedure for the synthesis of target derivatives
General procedure: Intermediate 4 (1mmol) and the intermediate 7 (1mmol) were dissolved in ethanol to the glass flask, then HCl solution was added as a catalyst refluxed at 80°C for 15-18h. After the TLC monitoring reaction was completed, the mixture was vacuum filtered and concentrated. Finally, the above crude product can be isolated and purified by column chromatography (Hexane/EtOAc=8:1) to obtain target compounds. |