Month: April 2021

Reference of 60434-13-1, The chemical industry reduces the impact on the environment during synthesis 60434-13-1, name is 5-Chloro-1-methylindoline-2,3-dione, I believe this compound will play a more active role in future production and life.

General procedure: A solution of N-methylisatin (322 mg, 2.0 mmol), phenylacetylene (306 mg, 3.0 mmol), CuI (76 mg, 0.4 mmol), and Cs2CO3 (978 mg, 3.0 mmol) in CH3CN (4.0 mL) was stirred at room temperature for 18 h. After aqueous extractive workup and column chromatographic purification process (CH2Cl2/EtOAc, 15:1) 1a was obtained as a pale yellow solid, 347 mg (66%).1-12 Other compounds were prepared similarly,1-12 and the propargylic alcohols were used in the next hydrogenation step without further identification process.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 5-Chloro-1-methylindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Note; Seo, Da Young; Min, Beom Kyu; Roh, Hwa Jung; Kim, Jae Nyoung; Bulletin of the Korean Chemical Society; vol. 38; 10; (2017); p. 1231 – 1234;,
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. 675109-26-9, name is 6-Bromoisoindolin-1-one, A new synthetic method of this compound is introduced below., COA of Formula: C8H6BrNO

(4) The compound obtained in step (3) (80 g, 0.38 mol) was dissolved in 1 L of dichloromethane.A 1 N solution of borane tetrahydrofuran (1 L) was added dropwise and stirred at room temperature for 4 hours.Then heated to reflux for 3 hours. The system cooled down,100 ml of 2N hydrochloric acid was added dropwise and the mixture was stirred at room temperature for 3 hours and then refluxed for 4 hours. Cooling filtration,The cake was washed with dichloromethane to give an off-white powder that was the target.

The synthetic route of 675109-26-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Xinyuan Pharmaceutical Technology Co., Ltd.; Wu Tianjun; (9 pag.)CN107474006; (2017); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 1168150-46-6, 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. 1168150-46-6, name is (E)-Methyl 3-(methoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A mixture of intermediate (3a, 3b, 6a, 6b, 10a, 10b, 11a-d, and14a-g, 1.5 mmol) and methyl (E)-3-(methoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate (1.5 mmol) in methanol (10 mL) wasstirred under reflux for 5-10 h. When TLC showed the completionof the reaction, the solution was cooled to room temperature. Theprecipitate was filtered off to give a crude product, which wasrecrystallized from methanol to provide the target compounds.

The synthetic route of (E)-Methyl 3-(methoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Qin, Mingze; Tian, Ye; Sun, Xiaoqing; Yu, Simiao; Xia, Juanjuan; Gong, Ping; Zhang, Haotian; Zhao, Yanfang; European Journal of Medicinal Chemistry; vol. 139; (2017); p. 492 – 502;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 40314-06-5, name is 5-Methylisoindoline-1,3-dione, molecular formula is C9H7NO2, 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. Recommanded Product: 5-Methylisoindoline-1,3-dione

N-4-methylphenylglycine ethyl ester (0.3 mmol) under air atmosphere,A phthalimide compound (0.2 mmol) and cuprous chloride (0.02 mmol) were placed in a dry reaction tube with stirring magnets.Then into the test tubeAn acetonitrile solvent (2 mL) was added and the reaction tube was reacted in an air atmosphere at 60 C for 24 hours.After the reaction was completed, it was cooled to room temperature, and the solvent was distilled off under reduced pressure using a rotary evaporator.The residue was purified by column chromatography to give a pure pale yellow solid 3 mThe yield was 65%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 40314-06-5, its application will become more common.

Reference:
Patent; Donghua University Of Science And Technology; Zhu Zhiqiang; Xiao Lijin; Xie Zongbo; Yue Changgao; (12 pag.)CN108623514; (2018); A;,
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. 110568-64-4, name is 6-Nitroisoindolin-1-one, A new synthetic method of this compound is introduced below., Recommanded Product: 110568-64-4

Synthesis of tert-butyl 5-nitro-1-oxoisoindoline-2-carboxylate (2) To a stirred solution of 5-nitroisoindolin-1-one (1, 0.4 g, 2.24 mmol) in acetonitrile (20 mL), N,N-dimethylaminopyridine (0.41 g, 3.37 mmol) followed by di-tert-butyl dicarbonate (0.75 mL, 3.37 mmol) were added. The reaction mixture was allowed to stir at room temperature for 12 h. The reaction mixture was quenched with water and extracted with ethyl acetate. The organic layer was washed with brine, separated, dried over sodium sulphate and concentrated under reduced pressure. The crude was purified by silica gel column chromatography using 25% ethyl acetate in hexane to afford tert-butyl 5-nitro-1-oxoisoindoline-2-carboxylate (2). Yield: 0.36 g, 57%; MS (ESI) m/z 279 [M+1]+.

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; eFFECTOR Therapeutics, Inc.; Sprengeler, Paul A.; Reich, Siegfried H.; Ernst, Justin T.; Webber, Stephen E.; Shaghafi, Mike; Murphy, Douglas; Tran, Chinh; (131 pag.)US10112955; (2018); B2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 20870-78-4, 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. 20870-78-4 name is 5-Bromoindolin-2-one, 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.

5-Bromo-2-oxindole 16 (150 mg, 0.71 mmol), benzeneboronic acid (113 mg, 0.92 mmol), tetrakis(triphenylphosphine)palladium(0) (61 mg, 0.05 mmol) and Natrium carbonate (250 mg, 2.41 mmol) were suspended in toluene (1.5 mL) and ethanol (1.5 mL) and refluxed for 12 h at 100 C. Water was added and extracted 3 times with ethyl acetate. The combined organic layers were wash with 1N hydrochloric acid, brine, dried over MgSO4, filtered and concentrated in vacuum to give 75 mg (51%) as a light brown solid and was used for the next step without further structure determination.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromoindolin-2-one, and friends who are interested can also refer to it.

Reference:
Article; Goering, Stefan; Taymans, Jean-Marc; Baekelandt, Veerle; Schmidt, Boris; Bioorganic and Medicinal Chemistry Letters; vol. 24; 19; (2014); p. 4630 – 4637;,
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. 141452-01-9, name is Methyl indoline-5-carboxylate, A new synthetic method of this compound is introduced below., HPLC of Formula: C10H11NO2

The indoline-5-carboxylate (177mg, 1.0mmol) was dissolved in pyridine (4mL), and4- (4- (2- (3- (chlorosulfonyl) benzamido) -4,5,6,7-tetrahydro-benzo [b] thiophen-3-carboxamido) phenethyl) benzoate (800mg, 1.26mmol),The reaction was heated to reflux for 18 hours.The reaction solution was diluted with ethyl acetate (80mL),0.1mol / L hydrochloric acid and washed (10mL ¡Á 3).The organic phase was dried over anhydrous sodium sulfate,concentrate.The crude product was purified by silica gel column chromatography (petroleum ether / dichloromethane (v / v) = 1/1) to give a yellow solid 491mg,Yield: 63.2%.

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; Guangdong East Sunshine Pharmaceutical Co., Ltd.; Wang, Xiaojun; Yang, Xinye; Zhou, Pingjian; Yang, Chuanwen; Lin, Jihua; Xiong, Shaohui; Zhang, Yingjun; Xiao, Ying; Wang, Hui; Cao, Shengtian; Wu, Fangyuan; Ouyang, Luo; (74 pag.)CN105524053; (2016); A;,
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.

6-Nitroindoline (5 g) was dissolved in 200 mL ofdichloroethane. N-Methyl-4-piperidone (5 g) was added to themixture, followed by NaHB(OAc)3 (12 g) and 1 mL of glacialAcOH. The mixture was stirred at RT overnight. A saturatedNaHC03 (200 mL) solution was added to the reaction mixtureand stirred for 1 h. The resulting mixture was separated byseparation funnel. The organic layer was extracted once withsaturated NaHC03 solution and once with brine. The resultingorganic layer was dried over MgS04, filtered andconcentrated in vacuo. The crude material was purified byflash chromatography on silica gel with 2:1 EtOAc:MeOH toafford orange oil. MS: 262 (M+l) . Calc’d. for C14H19N302 -261.3.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Nitroindoline, its application will become more common.

Reference:
Patent; AMGEN INC.; WO2006/12374; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 5428-09-1, name is 2-Allylisoindoline-1,3-dione, 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 5428-09-1, SDS of cas: 5428-09-1

To a solution of 2-allylisoindoline-1,3-dione 11(13.0 g, 69.4 mmol) in CH2CI2 (500 mL) was added AIIyITMS (79.0 g, 110 mL, 694 mmol) and Grubbs I generation catalyst. The reaction was heated to 60 ¡ãC and stirred under reflux for 4 h.Tris(hydrodxymethyl)phosphine (1 M solution in i-PrOH, 58 mL) was added and stirred under reflux for 12 h, while the color of the reaction turned from black to orange. Sat. aq. NaCI solution (100 mL) was added to the reaction and the organic phase was separated. The aqueous phase was extracted with CH2CI2 (3 x 200 mL). The combined organic layers were dried over MgSO4 and the solvent was removedunder reduced pressure. Column chromatography over SiC2 (Cyclohexane/ EtOAc =85:15) afforded the title compound (15.0 g, 54.9 mmol, 78.9 percent) as a yellow resin.R: 0.57 (Cyclohexane/EtOAc = 85:15)1H NMR (300 MHz, CDCI3) 6 = -0.10?0.09 (m, 9H), 1.44 (d, J = 8.2 Hz, 1.6 H), 1.72(d, J= 8.8 Hz, 0.4 H), 4.21 (d, J= 6.5 Hz, 1.6 H), 4.29 (dd, J= 14.5, 5.9 Hz, 0.4 H),5.26 ? 5.47 (m, 0.8 H), 5.56 ? 5.70 (m, 0.2 H), 5.70 ? 5.87 (m, 0.8 H), 5.94 ? 6.09 (m,0.2 H), 7.65 ? 7.74 (m, 2H), 7.79 ? 7.88 (m, 2H).?3C NMR (75 MHz, cdcl3) 6 = -2.05, -1.83, -1.43, 18.92, 22.73, 34.72, 39.87, 120.51,121.30, 123.12, 130.78, 132.24, 133.76, 133.90, 167.99.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Allylisoindoline-1,3-dione, and friends who are interested can also refer to it.

Reference:
Patent; MAX-PLANCK-GESELLSCHAFT ZUR FOeRDERUNG DER WISSENSCHAFTEN E.V.; WANG, Yansong; HAUSCH, Felix; BISCHOFF, Matthias; POMPLUN, Sebastian; WO2015/110271; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 1914-02-9, name is 3,3-Dimethylindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 3,3-Dimethylindoline

EXAMPLE 1 N-(3,3-Dimethylindolin-1-yl)-3-(4-imidazolyl)propionamide monohydrochloride (E1) STR9 A suspension of 3-(4-imidazolyl)propionic acid monohydrochloride (2.0 g) (Chem. Ber. 66, 156 [1933]) in thionyl chloride (10 ml) and DMF (3 drops) was stirred at room temperature for 3 h. The excess thionyl chloride was removed by rotary evaporation and the residue re-evaporated with 2*50 ml of dry toluene. The residue was suspended in CH2 Cl2 (100 ml) and a solution of 3,3-dimethyl indoline (1.7 g) and triethylamine (4 ml) in CH2 Cl2 (50 ml) was added with stirring and cooling. The reaction mixture was stirred overnight, washed with saturated NaHCO3 and the lower organic layer dried (Na2 SO4). Concentration of the organic extracts afforded the crude product which was purified by column chromatography on silica, eluding with CHCl3 containing increasing quantities of methanol.

The synthetic route of 1914-02-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Beecham Group p.l.c.; US4918079; (1990); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem