Category: 19727-83-4

Related Products of 19727-83-4, A common heterocyclic compound, 19727-83-4, name is 6-Nitroindoline, molecular formula is C8H8N2O2, 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.

9.84 g (0.06 mol) of 6-nitro-2,3-dihydro-1H-indole (16) was dispersed in 100 ml of dichloromethane under a nitrogen atmosphere, stirred at room temperature for about 10 minutes,11.8 g (0.12 mol) of cyclohexanone, 8.6 ml (0.15 mol) of acetic acid,29.7 g (0.14 mol) of sodium triacetoxy borohydride were added in this order, and the reaction solution was reacted at room temperature for 4 hours.200 ml of 1 N aqueous sodium hydroxide solution was slowly added to the reaction mixture, and the mixture was stirred for 30 minutes. The organic layer was separated, washed with H2O,The recovered organic layer was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The resulting product was dispersed in 100 ml of methanol, stirred at room temperature for 30 minutes, filtered and dried to obtain 6-nitro-2,3-dihydro -1-cyclohexyl-1H-indole (55) (12.7 g, 86.0%).

The synthetic route of 19727-83-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Korea Research Institute of Chemical Technology; Shin Seung-rim; Jeon Geun; Shin Jong-il; Park Yeong-il; Ahn Gyeong-ryong; (48 pag.)KR101842495; (2018); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 19727-83-4, 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. 19727-83-4, name is 6-Nitroindoline, This compound has unique chemical properties. The synthetic route is as follows.

To a mixture of 6-nitroindoline (2 mmol) and TEA (2.2 mmol) in CH2Cl2 (20 mL) was added di-tert-butyl dicarbonate (2 mmol). The mixture was stirred at 25 C. for 16 h. The mixture was washed with satd. aq. NaHCO3 (20 mL) and brine (20 mL), and then was dried and concentrated.

The chemical industry reduces the impact on the environment during synthesis 6-Nitroindoline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Carruthers, Nicholas I.; Chai, Wenying; Dax, Scott L.; Jablonowski, Jill A.; Li, Xiaobing; Lovenberg, Timothy W.; Murray, William V.; Rudolph, Dale A.; Seierstad, Mark; Youngman, Mark A.; US2005/70534; (2005); A1;,
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. 19727-83-4, name is 6-Nitroindoline, A new synthetic method of this compound is introduced below., Product Details of 19727-83-4

The tert-butyl 6-aminoindoline-l-carboxylate used as a starting material was prepared as follows :-Di-tert-butyl dicarbonate (7.2 g) was added to a mixture of 6-nitroindoline (4.92 g) and methylene chloride (50 ml) and the mixture was stirred at ambient temperature for 1 hour. 4-Dimethylaminopyridine (0.37 g) was added and the reaction mixture was stirred at ambient temperature for 16 hours. The resultant mixture was evaporated and the residue was purified by column chromatography on silica using increasingly polar mixtures of petroleum ether (b.p. 40-60C) and ethyl acetate as eluent. There was thus obtained tert-butyl 6-nitroindoline- 1-carboxylate as a solid (5.45 g); 1H NMR: (CDCl3) 1.6 (s, 9H), 3.2 (t, 2H), 4.1 (t, 2H), 7.2 (d, IH), 7.85 (d, IH), 8.3 (br s, 0.5H), 8.7 (br s, 0.5H).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/99317; (2007); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 19727-83-4, name is 6-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 19727-83-4, name: 6-Nitroindoline

Step A: 6-Nitroindoline (3.0 g, 18.3 mmol) was dissolved in THF (45 mL) and Et3N (3.4 mL, 24.4 mmol) at O0C. Acetyl chloride (1.5 mL, 21 mmol) was added drop wise. The mixture was stirred at room temperature for 30 minutes. The mixture was partitioned between EtOAc and aqueous HCl. The organic layer was dried and concentrated to yield l-acetyl-6-nitroindoline (3.8 g, 100%) as a yellow solid.

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; PTC THERAPEUTICS, INC.; HWANG, Peter Seongwoo; TAKASUGI, James; REN, Hongyu; WILDE, Richard Gerald; TURPOFF, Anthony; AREFOLOV, Alexander; KARP, Gary Mitchell; CHEN, Guangming; CAMPBELL, Jeffrey Allen; WO2006/19831; (2006); A1;,
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. 19727-83-4, name is 6-Nitroindoline, A new synthetic method of this compound is introduced below., Recommanded Product: 19727-83-4

To a solution of 6-nitroindoline (1.00 g, 6.09 mmol) and pyridine (1.48 mL, 18.27 mmol) in DCM (3 mL) was added a solution of t- butylsulfinyl chloride (0.751 mL, 6.09 mmol) at 0 C under Argon. The mixture was warmed to room temperature and stirred overnight. The reaction mixture was diluted with EtOAc (50 mL) and washed with HC1 (1 M aq. solution, 1 x 50 mL), water (1 x 50 mL), and brine (1 x 50 mL). The organic layer was dried (Na2S04) and concentrated under reduced pressure. The resulting residue was triturated using EtOAc/hexanes to provide the title compound as a dark yellow solid (1.252 g, 77%). Mp: 108 C (dec). NMR (400 MHz, CDCb) delta: 7.82 (dd, / = 8.1, 2.1 Hz, 1H), 7.67 (d, / = 2.1 Hz, 1H), 7.25 (d, / = 8.1 Hz, 1H), 4.36 (td, / = 10.5, 6.8 Hz, 1H), 3.60 (td, / = 10.5, 6.8 Hz, 1H), 3.30 (dddd, / = 17.3, 10.5, 6.8, 0.8 Hz, 1H), 3.17 (dddd, / = 17.3, 10.5, 6.8, 0.8 Hz, 1H), 1.34 (s, 9H). HPLC-MS (ESI+): m/z 559.3 [70%, (2M+Na)+], 291.2 [100%, (M+H)+].

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; H. LEE MOFFITT CANCER CENTER & RESEARCH INSTITUTE, INC.; SCHOeNBRUNN, Ernst; LAWRENCE, Nicholas J.; LAWRENCE, Harshani R.; (293 pag.)WO2017/66428; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 19727-83-4,Some common heterocyclic compound, 19727-83-4, name is 6-Nitroindoline, molecular formula is C8H8N2O2, 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.

Example 61 5-(6-(6-nitroindoline-1-carbonyl)pyrimidin-4-ylamino)-1,3-dihydrospiro[indene-2,3′-pyrrolo-[2,3-b]pyridin]-2′(1’H)-one 150 mg (0.37 mmol) 6-(2′-oxo-1,1′,2′,3-tetrahydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-5-ylamino)pyrimidine-4-carboxylic acid-hydrochloride, 60 mg (0.37 mmol) 4-nitroindole, 0.15 mL (0.87 mmol) DIPEA and 130 mg (0.41 mmol) TBTU in 1.8 mL DMF were stirred overnight at RT. Then the reaction mixture was diluted with water/MeOH, the precipitate formed was suction filtered and washed with plenty of water. The precipitate was dried. Yield: 165 mg (74% of theory) ESI-MS: m/z=520 (M+H)+ Rt (HPLC-MS): 1.56 min (method C)

The synthetic route of 19727-83-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2011/21500; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 19727-83-4, A common heterocyclic compound, 19727-83-4, name is 6-Nitroindoline, molecular formula is C8H8N2O2, 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.

To an oven dried flask equipped with a stir bar cooled under an inert atmosphere was added 6- nitroindoline (1.0 grams, 6.10 mmol, 0.3 M in anhydrous dichloromethane). While stirring at room temperature triethylamine (1.7 mL, 12.2 mmol) was added followed by chloroacetylchloride (0.63 mL, 7.9 mmol). The reaction stirred overnight. The next day the reaction was diluted with water and extracted using chloroform. The aqueous layer was washed with chloroform twice more. The combined organic material was washed with brine, dried with Na2S04, filtered, and concentrated. It was then used without any further purification. (1.39 grams collected). Calculated mass for C10H9CIN2O3, 240.03, observed mass, 241.0 (M+l, CI).

The synthetic route of 19727-83-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MUSC FOUNDATION FOR RESEARCH DEVELOPMENT; U.S. DEPARTMENT OF VETERANS AFFAIRS; LINDSEY, Christopher, C.; BEESON, Craig, C.; SCHNELLMANN, Rick, G.; (51 pag.)WO2018/85491; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 19727-83-4, 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 19727-83-4 as follows.

General procedure: In a 2-neck RBF, 1 (20 mg, 0.0005 mmol) and TMNO (45 mg, 0.6 mmol) were suspended in toluene (4 mL) and to this solution indoline (60 mg, 0.5 mmol) was added. The reaction mixture was then heated to 100 oC for 20 h and it was filtered and solvent evaporated. The crude product obtained was purified by column chromatography using hexane/ethylacetate (7:1) as eluent to give pure indole (47 mg, 79%). A similar procedure was used for the other indolines and N-heterocycles.

According to the analysis of related databases, 19727-83-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kumaran, Elumalai; Leong, Weng Kee; Tetrahedron Letters; vol. 59; 44; (2018); p. 3958 – 3960;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

19727-83-4, name is 6-Nitroindoline, belongs to indolines-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Safety of 6-Nitroindoline

To a stirred solution of 6-nitroindoline (8.0 g, 48.8 mmol) in DCM (50 ml_) was added pyridine (9.9 ml_, 122 mmol), (Boc)2O (10.6g, 48.6 mmol) and catalytic DMAP. EPO The mixture was stirred overnight. Reaction was washed with brine, and the organic layer was dried (Na2SO4), filtered and concentrated. Chromatography (20% EtOAc/hexanes) provided 1-Boc-6-nitroindoline (10 g, 78%).

The synthetic route of 19727-83-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; PHARMACOPEIA DRUG DISCOVERY, INC.; WO2007/24944; (2007); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 19727-83-4, name is 6-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. Safety of 6-Nitroindoline

1-Methyl-2,3-dihydro-1H-indol-6-ylamine. 6-Nitroindoline (2 mmol) was combined with methyl iodide (2.2 mmol), n-Bu4I (7.4 mg, 0.020 mmol), and K2CO3 (350 mg, 2.5 mmol) in acetone (10 mL). The mixture was stirred at 25 C. for 16 h. The mixture was partitioned between CH2Cl2 and satd. aq. NaHCO3 (20 mL), and the organic layer was dried and concentrated. Purification by silica gel chromatography provided 1-methyl-6-nitroindoline (300 mg, 84%).

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

Reference:
Patent; Carruthers, Nicholas I.; Chai, Wenying; Dax, Scott L.; Jablonowski, Jill A.; Li, Xiaobing; Lovenberg, Timothy W.; Murray, William V.; Rudolph, Dale A.; Seierstad, Mark; Youngman, Mark A.; US2005/70534; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem