Category: indolines-derivatives

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. 56341-37-8, name is 6-Chlorooxindole, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C8H6ClNO

EXAMPLE 20c; Preparation of intermediate E/Z-3-[4-Chloro-2-(6-chloro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-phenoxy]-2,2-dimethyl-propionic acid methyl ester; 3-(4-chloro-2-formyl-phenoxy)-2,2-dimethyl-propionic acid methyl ester (6.7 g, 25 mmol) and 6-Chloro-1,3-dihydro-indol-2-one (4.35 g, 25 mmol) were mixed in 20 mL of anhydrous methanol. Then pyrrolidine (2 mL, 25 mmol) was added dropwise at r.t. The mixture was heated to 70 C. for 3 h and cooled to room temperature. The precipitate was collected by filtration and dried to give title compound as yellow solid (Yield: 7 g, 67%).m/z (M+H)+: 420

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 56341-37-8.

Reference:
Patent; Chen, Li; Han, Xingchun; He, Yun; Yang, Song; Zhang, Zhuming; US2009/163512; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 172078-33-0, 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. 172078-33-0, name is Indolin-5-ol belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Example 49: 5-Hydroxy-2,3-dihydro-indole-l-carboxylic acid tert-butyl esterA mixture of 2,3-dihydro-lH-indol-5-ol (1.0 g, 7.8 mmol), di-te/t-butyldicarbonate (4.0 g, 18 mmol), chloroform (20 mL) and saturated sodium bicarbonate aq. (8 mL) was stirred at room temperature over night. The organic phase was separated and washed twice with water, dried over MgSO4, filtered and concentrated to give crude product. The crude material was treated with ether and filtered to give product (1.1 g, yield: 60%). ESI-MS: 258.10 (M+23)+, 1H NMR (400 MHz, DMSO) delta 9.00 (s, IH), 7.48 (ws, IH), 6.61 (d, IH), 6.51 (dd, IH), 3.84 (t, 2H), 2.96 (t, 2H), 1.48 (s, 9H).

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

Reference:
Patent; BIOGEN IDEC MA INC.; THOMAS, Jermaine; LIU, Xiaogao; LIN, Edward, Yin-Shiang; ZHENG, Guo, Zhu; MA, Bin; CALDWELL, Richard, D.; GUCKIAN, Kevin, M.; KUMARAVEL, Gnanasambandam; TAVERAS, Arthur, G.; WO2011/17561; (2011); A1;,
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. 883-44-3, name is 2-(3-Hydroxypropyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C11H11NO3

Compound 330(2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(((3-((5-(tert-butyl)-lH-benzo[d]imidazol- 2-yl)amino)propyI)amino)methyl)tetrahydrofuran-3,4-diolStep 1. Preparation of 3-(l,3-dioxoisoindolin-2-yl)propanal2-(3-hydroxypropyl)isoindoline-l,3-dione (414 mg, 2.0 mmol) and IBX (1.68 g, 6 mmol) were dissolved in EA (25 mL) and the reaction mixture was heated to reflux with stirring for 3 h. And then the mixture was filtrated and rinsed with EA (15 mL x 3), the filtrate was concentrated to afford the product (crude, 412 mg, yield: 100 %) as a yellow solid which was directly used for next step without further purification.

According to the analysis of related databases, 883-44-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; EPIZYME, INC.; CHESWORTH, Richard; KUNTZ, Kevin, Wayne; OLHAVA, Edward, James; PATANE, Michael, A.; WO2012/82436; (2012); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 954-81-4, name is N-(5-Bromopentyl)phthalimide, 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 954-81-4, Safety of N-(5-Bromopentyl)phthalimide

60 g (0.302 mol) N-[(E)-4-pyridylmethyleneamino]aniline in 350 ml N,N-dimethyl5 formamide were stirred at 20C under argon atmosphere. The reaction mixture wascooled down -30C. 22 g (0.903 mol) sodium hydride was added slowly while keeping the reaction temperature below -25C. Afterwards, a solution of 121 g (0.452 mol) N-(5-bromopentyl)phthalimide in 500 ml N,N-dimethylformamide was added into the mixturedropwise within one hour. After the addition, the product mixture was warmed to 20Cand continued to stir for another 12 hours. Then, the reaction was quenched by adding20 ml water. Another 600 ml water were poured into the reaction mixture. The formedprecipitate was collected by filtration and washed with distilled water. The obtainedcrude product was used for the next step directly without further purification.Yield: 88 g (75%), yellow solid.ESI-MS m/z 412.2 [W].

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, N-(5-Bromopentyl)phthalimide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BASF SE; BACHMANN, Frank; CREMER, Christian; FROEHLING, Beate; MURPHY, Bryan Patrick; ZHANG, Guiru; TORGERSON, Peter Marte; (123 pag.)WO2016/146813; (2016); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 104618-32-8, 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 104618-32-8 as follows.

To a solution of the title compound from above step A (1.5 g, 6.7 mmol) in ethanol (100 mL) was added ketone derivative (1.6 g, 6.7 mmol) in ethanol (50 mL). The reaction mixture was stirred for 5 h at room temperature. The solvent was removed to give the title compound as a solid (3.1, quantitative). The product was used in the next step without any purification.

According to the analysis of related databases, 104618-32-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AC Immune, S.A.; US2011/280808; (2011); A1;,
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 13220-46-7 as follows. name: 4-Methylindolin-2-one

Example 76 (R,Z)-5-(2-hydroxy-3-morpholinopropyl)-3-methyl-2-((4-methyl-2-oxoindolin-3-ylidene)methyl)-5,6,7,8-tetrahydropyrrolo[3,2-c]azepin-4(1H)-one 5-(2-Hydroxy-3-morpholin-4-yl-propyl)-3-methyl-4-oxo-1,4,5,6,7,8-hexahydro-pyrrolo[3,2-c]azepine-2-carbaldehyde 53f (30 mg, 0.09 mmol) and 4-methyl-1,3-dihydro-indol-2-one (12 mg, 0.08 mmol) were dissolved in 156 mul of ethanol, and added with 4.4 mul of piperidine to the solution at room temperature. Upon completion of the addition, the reaction mixture was stirred at 45 C. for 16 hours. After thin lay chromatography showed the disappearance of starting materials, the reaction mixture was naturally cooled down to room temperature, and filtered. The filter cake was washed with anhydrous ethanol (1 ml*2) and dried to obtain the title compound (R,Z)-5-(2-hydroxy-3-morpholinopropyl)-3-methyl-2-((4-methyl-2-oxoindolin-3-ylidene)methyl)-5,6,7,8-tetrahydropyrrolo[3,2-c]azepin-4(1H)-one 76 (12 mg, yield 30%) as a orange solid.

According to the analysis of related databases, 13220-46-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ChoTang, Peng Cho; Su, Yidong; Li, Yali; Zhang, Lei; Zhao, Fuqiang; Yang, Jialiang; Zhou, Ying; Bie, Pingyan; Qian, Guangtao; Ju, Minggang; US2010/75952; (2010); 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. 17702-83-9, name is 2-(8-Bromooctyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Formula: C16H20BrNO2

General procedure: 2-(omega-Bromoalkyl)-isoindoline-1,3-dione (1 equiv) with N-methylbenzylamine (1 equiv) or its substituted analog in the presence of K2CO3 (3 equiv) was stirred in acetonitrile under reflux for 16 h. Once the reaction was finished, the solvent was evaporated under vacuum, producing a residue that was further dissolved in 50 mL of 5 M NaOH and extracted with ethyl acetate (3 x 50 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (dichloromethane to dichloromethane/methanol 98:2), yielding a yellow oil. The final product was obtained in the form of hydrochloride salt. The following compounds were obtained.

The synthetic route of 17702-83-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Guzior, Natalia; Bajda, Marek; Rakoczy, Jurand; Brus, Boris; Gobec, Stanislav; Malawska, Barbara; Bioorganic and Medicinal Chemistry; vol. 23; 7; (2015); p. 1629 – 1637;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 675109-26-9, These common heterocyclic compound, 675109-26-9, name is 6-Bromoisoindolin-1-one, 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.

A mixture of 6-bromoisoindolin-1-one (287 mg, 1.35 mmol), 1-methyl-5-(tributylstannyl)-1H-imidazole (500 mg, 1.35 mmol), Pd(dppf)Cl2 (33 mg, 0.041 mmol) and Cs2CO3 (1.32 g, 4.05 mmol) in dioxane (50 mL) and water (8 mL) was heated to 100 C. overnight. After cooling, the mixture was concentrated under vacuum and purified by column chromatography on silica gel ((1%-3% MeOH in DCM) to afford 9A (220 mg, 76% yield) as a brown solid: 1H NMR (400 MHz, DMSO-d6) delta 8.66 (s, 1H), 7.76-7.15 (m, 4H), 7.15 (s, 1H), 4.43 (s, 2H), 3.72 (s, 3H); ESI m/z 214.1 [M+1]+.

Statistics shows that 6-Bromoisoindolin-1-one is playing an increasingly important role. we look forward to future research findings about 675109-26-9.

Reference:
Patent; Seal Rock Therapeutics, Inc.; BROWN, Samuel David; US2018/291002; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 19727-83-4, 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. 19727-83-4 name is 6-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: Into a Schlenk tube (volume: ca. 20 mL) connected to a balloon partially filled with Ar gas, Pd/LDH (75 mg, Pd: 3 mol %), 4-isopropylpiperidine (0.5 mmol), decane (internal standard, 0.1 mmol), octane (2.0 mL), and a Teflon-coated magnetic stir bar were successively placed, and the reaction mixture was vigorously stirred at 120 C, in 1 atm of Ar. After the reaction was completed, the conversion of 4-isopropylpiperidine and the yield of 4-isopropylpyridine were determined by GC analysis. The reactions of piperidine and 4-methylpiperidine were conducted in a test tube with an Ar balloon. During these reactions, the upper side of the test tube was cooled by refrigerant (-5 C).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Nitroindoline, and friends who are interested can also refer to it.

Reference:
Article; Oyama, Takashi; Yatabe, Takafumi; Jin, Xiongjie; Mizuno, Noritaka; Yamaguchi, Kazuya; Chemistry Letters; vol. 48; 6; (2019); p. 517 – 520;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 7477-63-6, The chemical industry reduces the impact on the environment during synthesis 7477-63-6, name is 7-Chloroisatin, I believe this compound will play a more active role in future production and life.

General procedure: Mg(ClO4)2 (10 mol percent) was added to a mixture of isatin (2 mmol), malononitrile or ethyl cyanoacetate (2mmol), and dimedone (2 mmol) in aqueous ethanol solution(50percent, v/v, 5 mL), and the resulting mixture was stirred at 50¡ãC for 30-60 min. Upon completion of the reaction (TLC),the mixture was allowed to cool to room temperature. The resulting solid was filtered and washed successively with water (2 ¡Á 30 mL) and cold aqueous ethanol (2 ¡Á 1 mL) to afford pure product 4.

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, 7-Chloroisatin, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Wu, Chunlei; Shen, Runpu; Chen, Jianhui; Hu, Chunqi; Bulletin of the Korean Chemical Society; vol. 34; 8; (2013); p. 2431 – 2435;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem