Category: 32692-19-6

Reference of 32692-19-6, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 32692-19-6, name is 5-Nitroindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: We described the synthesis of the compound 1 (Table 2) to illustrate the general procedure for TFA accelerated Petasis three-component reaction. The descriptions of the preparations of all reported compounds are in the Supporting information section. To a magnetically stirred mixture of 5-nitroindoline (0.164 g, 1.0 mmol), 4-tolyboronic acid (0.135 g, 1.0 mmol), and glyoxylic acid monohydrate (0.092 g, 1.0 mmol) in CH2Cl2 (5 ml) was added TFA (20 mul). The mixture was stirred at room temperature for 4 h. After the completion of the reaction (TLC monitoring), half of the solvent was evaporated by means of a rotovap. The resulting solid was filtered through a sintered glass funnel. The collected solid was thoroughly washed with petroleum ether and a small amount of ice water (5 ml), and then dried in vacuo at room temperature for 24 h to afford 0.26 g (83.3 %) of 2-(5-nitroindolin-1-yl)-2-(p-tolyl) acetic acid as a light yellow solid.

The synthetic route of 5-Nitroindoline has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Jing; Yun, Fan; Xie, Rui; Cheng, Chunhui; Chen, Guangyao; Li, Jingxuan; Tang, Pingwah; Yuan, Qipeng; Tetrahedron Letters; vol. 57; 35; (2016); p. 3916 – 3919;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 32692-19-6, name is 5-Nitroindoline, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C8H8N2O2

General procedure: We described the synthesis of the compound 1 (Table 2) to illustrate the general procedure for TFA accelerated Petasis three-component reaction. The descriptions of the preparations of all reported compounds are in the Supporting information section. To a magnetically stirred mixture of 5-nitroindoline (0.164 g, 1.0 mmol), 4-tolyboronic acid (0.135 g, 1.0 mmol), and glyoxylic acid monohydrate (0.092 g, 1.0 mmol) in CH2Cl2 (5 ml) was added TFA (20 mul). The mixture was stirred at room temperature for 4 h. After the completion of the reaction (TLC monitoring), half of the solvent was evaporated by means of a rotovap. The resulting solid was filtered through a sintered glass funnel. The collected solid was thoroughly washed with petroleum ether and a small amount of ice water (5 ml), and then dried in vacuo at room temperature for 24 h to afford 0.26 g (83.3 %) of 2-(5-nitroindolin-1-yl)-2-(p-tolyl) acetic acid as a light yellow solid.

According to the analysis of related databases, 32692-19-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zhang, Jing; Yun, Fan; Xie, Rui; Cheng, Chunhui; Chen, Guangyao; Li, Jingxuan; Tang, Pingwah; Yuan, Qipeng; Tetrahedron Letters; vol. 57; 35; (2016); p. 3916 – 3919;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 32692-19-6, name is 5-Nitroindoline, belongs to indolines-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 32692-19-6, Recommanded Product: 32692-19-6

Example 7 1-methylethyl 4-[4-(5-nitro-2,3-dihydro-1H-indol-1-yl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]piperidine-1-carboxylate; [Show Image] To a mixture of 5-nitro-2,3-dihydro-1H-indole (328 mg, 2.00 mmol), 1-methylethyl 4-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)piperidine-1-carboxylate (323 mg, 1.00 mmol) obtained in Reference Example 3, and N,N-dimethylformamide (10 mL) was added potassium carbonate (830 mg, 6.01 mmol), and the mixture was stirred at 100C for 2 days. The reaction mixture was allowed to cool to room temperature, water was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated. The residue was crystallized from ethyl acetate to give the title compound as yellow crystals (175 mg, yield 39%). 1H-NMR (300 MHz, CDCl3)delta:1.28 (d, J = 6.0 Hz, 6 H), 1.82 – 1.99 (m, 2 H), 2.02 – 2.16 (m, 2 H), 2.91 – 3.08 (m, 2 H), 3.38 (t, J = 8.7 Hz, 2 H), 4.29 – 4.46 (m, 2 H), 4.65 (t, J = 8.7 Hz, 2 H), 4.87 – 5.02 (m, 2 H), 6.65 (d, J = 3.8 Hz, 1 H), 7.16 (d, J = 3.8 Hz, 1 H), 8.08 (s, 1 H), 8.17 (dd, J = 9.0, 2.3 Hz, 1 H), 8.57 (s, 1 H), 8.62 (d, J = 9.4 Hz, 1 H).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2399914; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 32692-19-6, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 32692-19-6 name is 5-Nitroindoline, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: We described the synthesis of the compound 1 (Table 2) to illustrate the general procedure for TFA accelerated Petasis three-component reaction. The descriptions of the preparations of all reported compounds are in the Supporting information section. To a magnetically stirred mixture of 5-nitroindoline (0.164 g, 1.0 mmol), 4-tolyboronic acid (0.135 g, 1.0 mmol), and glyoxylic acid monohydrate (0.092 g, 1.0 mmol) in CH2Cl2 (5 ml) was added TFA (20 mul). The mixture was stirred at room temperature for 4 h. After the completion of the reaction (TLC monitoring), half of the solvent was evaporated by means of a rotovap. The resulting solid was filtered through a sintered glass funnel. The collected solid was thoroughly washed with petroleum ether and a small amount of ice water (5 ml), and then dried in vacuo at room temperature for 24 h to afford 0.26 g (83.3 %) of 2-(5-nitroindolin-1-yl)-2-(p-tolyl) acetic acid as a light yellow solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Nitroindoline, and friends who are interested can also refer to it.

Reference:
Article; Zhang, Jing; Yun, Fan; Xie, Rui; Cheng, Chunhui; Chen, Guangyao; Li, Jingxuan; Tang, Pingwah; Yuan, Qipeng; Tetrahedron Letters; vol. 57; 35; (2016); p. 3916 – 3919;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 32692-19-6, These common heterocyclic compound, 32692-19-6, name is 5-Nitroindoline, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

9.30 g (213 mmol) of sodium hydride (purity 55%) and 100 mL of dehydrated DMF were added to a 500 mL two-necked flask, and a solution of 5-nitroindoline in DMF (5-nitroindoline: 35.0 g 213 mmol), DMF: 100 mL) was added dropwise so as not to exceed 30 C. After completion of the dropwise addition, the mixture was stirred at room temperature for 2 hours. To this reaction solution, a DMF solution of 4-fluoronitrobenzene (4-fluoronitrobenzene: 33.0 g (234.5 mmol), DMF: 100 mL) was added dropwise, and the mixture was stirred at room temperature for 6 hours under a nitrogen atmosphere.After completion of the reaction, 100 mL of pure water was slowly poured while stirring the reaction solution, and a solid was precipitated. The precipitated solid was filtered, dissolved again in DMF, poured into 500 mL of pure water, reprecipitated, and the solid was again collected by filtration and recovered . The obtained solid was dispersed and washed with methanol and n-hexane, and vacuum dried to obtain 54.7 g (yield: 90%) of an orange solid.

The synthetic route of 32692-19-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NISSAN CHEMICAL INDUSTRIES LIMITED; NODA, TAKAHIRO; TETSUTANI, HISASHI; (51 pag.)JP5839200; (2016); B2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 32692-19-6, name is 5-Nitroindoline, A new synthetic method of this compound is introduced below., name: 5-Nitroindoline

General procedure: To a stirred solution of aryl halides (1.0 mmol) and indoline/indoline carboxylic acid (1.0 equiv) in dry DMSO (2.0 mL) at rt was added nano CuO (5.0 mol %) followed by Cs2CO3 (2.0 equiv) and heated at 80 C for 8 h. The progress of the reaction was monitored by TLC. After the reaction was complete, the reaction mixture was cooled to room temperature and catalyst was filtered, the crude residue was extracted with ethyl acetate (3 × 10 mL). The combined organic layers were extracted with water, saturated brine solution, and dried over anhydrous Na2SO4. The organic layers were evaporated under reduced pressure and the resulting crude product was purified by column chromatography by using ethyl acetate/hexane (7:3) as eluent to give the corresponding N-substituted indoles in excellent yields. The identity and purity of the product were confirmed by 1H, 13C NMR, and mass spectra.

The synthetic route of 32692-19-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Reddy, K. Harsha Vardhan; Satish; Ramesh; Karnakar; Nageswar; Tetrahedron Letters; vol. 53; 24; (2012); p. 3061 – 3065;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 32692-19-6, name is 5-Nitroindoline, belongs to indolines-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 32692-19-6, COA of Formula: C8H8N2O2

A suspension of 5-nitroindoline (6) (1.0 g, 6.09 mmol) in toluene (20 mL) was treated with 2-chloroacetyl chloride (0.97 mL, 12.18 mmol) and heated at 110 C for 15 min. ;The reaction was cooled to room temperature, treated with sat. ;NaHCO3 solution and extracted into ethyl acetate. ;The combined organic layer was dried (Na2SO4) and concentrated. ;The crude was purified by flash column chromatography (EtOAc:hexanes, 1:9 to 1:1 then 2 M NH3 MeOH: ;CH2Cl2, 1:9) to obtain the title compound (1.08 g, 74%). ;1H NMR (CDCl3) delta 8.30-8.27 (m, 1H), 8.14 (dd, 1H, J = 2.1, 9.0 Hz), 8.06 (s, 1H), 4.30 (t, 2H, J = 8.7 Hz), 4.18 (s, 2H), 3.33 (t, 2H, J = 8.4 Hz); ESI-MS (m/z, %): 241, 243 (MH+).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Annedi, Subhash C.; Maddaford, Shawn P.; Ramnauth, Jailall; Renton, Paul; Rybak, Taras; Silverman, Sarah; Rakhit, Suman; Mladenova, Gabriela; Dove, Peter; Andrews, John S.; Zhang, Dongqin; Porreca, Frank; European Journal of Medicinal Chemistry; vol. 55; (2012); p. 94 – 107,14;; ; Article; Annedi, Subhash C.; Maddaford, Shawn P.; Ramnauth, Jailall; Renton, Paul; Rybak, Taras; Silverman, Sarah; Rakhit, Suman; Mladenova, Gabriela; Dove, Peter; Andrews, John S.; Zhang, Dongqin; Porreca, Frank; European Journal of Medicinal Chemistry; vol. 55; (2012); p. 94 – 107;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 32692-19-6, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 32692-19-6, name is 5-Nitroindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

In a 20 ml pressure tube were mixed 5-nitroindoline (500 mg, 3.05 mmol) and sodium carbonate (968 mg, 9.14 mmol) at ambient temperature in anhydrous tetrahydrofuran (5 ml). Methyl iodide (0.190 ml, 3.05 mmol) was added. The reaction mixture was stirred and heated for 24 hours at 60 C. the mixture was diluted with ethyl acetate and water, and the layers were separated. The organic layer was washed with brine, dried with Na2S04, filtered, and concentrated. The residue was purified by flash chromatography on a 40 g silica gel column using an AnaLogix IntelliFlash 280 system eluting with a gradient of 10 to 20% ethyl acetate/hexane to provide the title compound. MS (DCI(+)) m/e 179 (M+H)+.

The synthetic route of 5-Nitroindoline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBOTT LABORATORIES; BA-MAUNG, Nwe Y.; CLARK, Richard F.; ERICKSON, Scott A.; FIDANZE, Steve D.; KAWAI, Megumi; MANTEI, Robert A.; SHEPPARD, George S.; SORENSON, Bryan K.; WANG, Gary T.; WO2011/53476; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 32692-19-6, name is 5-Nitroindoline, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. category: indolines-derivatives

General procedure: We described the synthesis of the compound 1 (Table 2) to illustrate the general procedure for TFA accelerated Petasis three-component reaction. The descriptions of the preparations of all reported compounds are in the Supporting information section. To a magnetically stirred mixture of 5-nitroindoline (0.164 g, 1.0 mmol), 4-tolyboronic acid (0.135 g, 1.0 mmol), and glyoxylic acid monohydrate (0.092 g, 1.0 mmol) in CH2Cl2 (5 ml) was added TFA (20 mul). The mixture was stirred at room temperature for 4 h. After the completion of the reaction (TLC monitoring), half of the solvent was evaporated by means of a rotovap. The resulting solid was filtered through a sintered glass funnel. The collected solid was thoroughly washed with petroleum ether and a small amount of ice water (5 ml), and then dried in vacuo at room temperature for 24 h to afford 0.26 g (83.3 %) of 2-(5-nitroindolin-1-yl)-2-(p-tolyl) acetic acid as a light yellow solid.

The synthetic route of 5-Nitroindoline has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Jing; Yun, Fan; Xie, Rui; Cheng, Chunhui; Chen, Guangyao; Li, Jingxuan; Tang, Pingwah; Yuan, Qipeng; Tetrahedron Letters; vol. 57; 35; (2016); p. 3916 – 3919;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 32692-19-6 as follows. Formula: C8H8N2O2

General procedure: A solution of 5-nitroindoline (6) (0.5 g, 3.05 mmol) in DMF (10 mL) was treated with NaH (0.39 g, 9.75 mmol, 60% wt in mineral oil) at 0 C resulting in an orange mixture. ;The reaction mixture was then treated with 2-chloro-N,N-dimethylethanamine hydrochloride (0.87 g, 6.09 mmol) resulting in a dark red mixture. ;The reaction was heated to 90 C and stirred for 1.5 h. ;After allowing the reaction to cool to room temperature, water was added and the product was extracted into EtOAc. ;The combined ethyl acetate layer was washed with water, brine and dried (Na2SO4). ;Solvent was evaporated and the crude was purified by flash column chromatography (2 M NH3 in MeOH:CH2Cl2, 2.5:97.5) to obtain the title compound

According to the analysis of related databases, 32692-19-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Annedi, Subhash C.; Maddaford, Shawn P.; Ramnauth, Jailall; Renton, Paul; Rybak, Taras; Silverman, Sarah; Rakhit, Suman; Mladenova, Gabriela; Dove, Peter; Andrews, John S.; Zhang, Dongqin; Porreca, Frank; European Journal of Medicinal Chemistry; vol. 55; (2012); p. 94 – 107,14;; ; Article; Annedi, Subhash C.; Maddaford, Shawn P.; Ramnauth, Jailall; Renton, Paul; Rybak, Taras; Silverman, Sarah; Rakhit, Suman; Mladenova, Gabriela; Dove, Peter; Andrews, John S.; Zhang, Dongqin; Porreca, Frank; European Journal of Medicinal Chemistry; vol. 55; (2012); p. 94 – 107;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem