Indolines-derivatives

Electric Literature of 59-48-3,Some common heterocyclic compound, 59-48-3, name is Indolin-2-one, molecular formula is C8H7NO, 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.

PREPARATION H 5-Acetyloxindole The titled compound was prepared by reaction of oxindole with acetyl chloride and aluminum chloride in carbon disulfide.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Indolin-2-one, its application will become more common.

Reference:
Patent; Pfizer Inc.; US4678802; (1987); A;,
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 22190-33-6 as follows. Product Details of 22190-33-6

REFERENCE EXAMPLE 8 1-boc-5-Bromoindoline 5-bromoindoline (10 g) was added in one portion to molten Boc-anhydride (11.6 g) at 30-40 C. Immediate effervescence was followed by the formation of a solid cake which was triturated with pentane to give the title compound (15 g) as a white powder.

According to the analysis of related databases, 22190-33-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Aventis Pharma Ltd.; Aventis Recherche Developpment; US6608084; (2003); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 118289-55-7, A common heterocyclic compound, 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-one, molecular formula is C10H9Cl2NO, 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.

Example 5 Preparation of 5- [2- [4- (1, 2- benzisothiazol-3-yl) -1-piperazinyl] ethyl] -6-chloro-1, 3-dihydro-2H-indol-2-one (Ziprasidone base) Example 2 was repeated with the exception that 10 ml of 1-butyl-3-methylimidazolium bromide was used instead of 8 ml of 1-ethyl-3-methylimidazolium methyl sulfate. After the completion of the reaction the presence of 5- [2- [4- (1, 2- benzisothiazol-3-yl) -1-piperazinyl] ethyl] -6-chloro-1, 3- dihydro-2H-indol-2-one was confirmed by HPLC.

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; KRKA; EP1889844; (2008); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 87-48-9, name is 5-Bromoindoline-2,3-dione, molecular formula is C8H4BrNO2, 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: Isatin derivatives 1a-c (0.005 mol) were stirred in acetonitrile(20 mL) with (0.007 mol) of the appropriate methyl iodide 2, propyliodide 3 or benzyl bromide 7a-d in the presence of catalytic amountof potassium iodide with (0.010 mol) of dry potassium carbonate atreflux temperature. The reaction was monitored with TLC. Aftercomplete of reaction, the mixture was poured into ice-water, theformed solid was collected, washed with water and recrystallizedfrom ethanol-water to furnish the final compounds 4a-f and 8a-l[58-61].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 87-48-9, its application will become more common.

Reference:
Article; Eldehna, Wagdy M.; Abo-Ashour, Mahmoud F.; Nocentini, Alessio; El-Haggar, Radwan S.; Bua, Silvia; Bonardi, Alessandro; Al-Rashood, Sara T.; Hassan, Ghada S.; Gratteri, Paola; Abdel-Aziz, Hatem A.; Supuran, Claudiu T.; European Journal of Medicinal Chemistry; vol. 162; (2019); p. 147 – 160;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 17564-64-6, 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. 17564-64-6 name is 2-(Chloromethyl)isoindoline-1,3-dione, 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.

Example 17: (E)-3-[3′-Adamantan-l-yl-4′-(l,3-dioxo-l,3-dihydroisoindol-2- ylmethoxy)-biphenyl-4-yl] -acrylic acid ST5632AA1; STEP 1: A solution of (E)-3-(3′-adamantan-l-yl-4′-hydroxybiphenyl-4-yl)acrylic acid tert-hutyl ester (200 mg, 0.464 mmol), N-chloromethylphthalimide (91 mg, 0.464 mmol), K2CO3 (70 mg, 0.464 mmol) and NaI (70 mg, 0.464 mmol) was stirred overnight at RT in the dark. The solvent was evaporated and the residue was taken up in EtOAc. The organic phase was washed with water, dried over Na2SO4, filtered and evaporated under reduced pressure. 3-[3′- Adamantan-l-yl-4′-(l,3-dioxo-l,3-dihydroisoindol-2-ylmethoxy)-biphenyl-4- yl] acrylic acid tert-hutyl ester was obtained after purification on silica gel (EtOAc/hexane 15:85) in 55%yield (150 mg).1H NMR (DMSO-ds) delta: 7.30-8.05 (m, 12H); 6.55 (d, J = 16 Hz, IH); 5.70 (s, 2H); 2.05 (s, 6H); 1.95 (s, 3H); 1.60 (s, 6H); 1.50 (s, 9H).

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

Reference:
Patent; SIGMA-TAU INDUSTRIE FARMACEUTICHE RIUNITE S.P.A.; CABRI, Walter; GIANNINI, Giuseppe; BATTISTUZZI, Gianfranco; ALLOATTI, Domenico; PISANO, Claudio; DALLAVALLE, Sabrina; BRUNETTI, Tiziana; WO2010/72727; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, 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 102359-00-2, Recommanded Product: 2-Oxoindoline-5-carboxylic Acid

General procedure: A solution of 9a-d (2 mmol), EDCI (3 mmol) and HOBt (3 mmol) in dry DCM (20 mL) was stirred at 0C for 3.5 h. Then different substituted amines (2.2 mmol) and DIPEA (4 mmol) were added and the reaction was stirred at r.t. for another 1.5 h. The organic layer was washed with water and brine and dried over Na2SO4. Removal of the solvent gave a residue that was purified by column chromatography (silica gel, CH2Cl2-MeOH 100: 1 as an eluent) to furnish 10a-n as white solids.

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, 2-Oxoindoline-5-carboxylic Acid, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Guo, Jing; Zhu, Mingyue; Wu, Tianxiao; Hao, Chenzhou; Wang, Kai; Yan, Zizheng; Huang, Wanxu; Wang, Jian; Zhao, Dongmei; Cheng, Maosheng; Bioorganic and Medicinal Chemistry; vol. 25; 13; (2017); p. 3500 – 3511;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 88150-75-8, name is Ethyl 4-(2-(1,3-dioxoisoindolin-2-yl)ethoxy)-3-oxobutanoate, 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 88150-75-8, Formula: C16H17NO6

To a solution of ethyl 4-(2-phthalimidoethoxy)acetoacetate in toluene was added 3000 ml of isopropyl alcohol, 564 g of 2-chlorobenzaldehyde was added with stirring, 17 5g acetic acid, 24.8g piperidine; 20 ~ 30 C, stirring 9 ~ 10h, adding 589g beta-aminocrotonic acid methyl ester, heating to 55 ~ 58 C, and stirring at 55 ~ 58 C reaction, stirring 7h sampling, TLC plate to confirm the end of the reaction, cooling to below 25 C, adding 3200ml acetic acid; then seeded to 0 ~ 5 C, the same temperature for 5h, crystallization; filtration crystallization, with 800ml isopropyl alcohol washing, the wash was run twice (400 ml each) and dried under reduced pressure to give 1611 g of phthaloyl amlodipine in a yield of 76.1%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 4-(2-(1,3-dioxoisoindolin-2-yl)ethoxy)-3-oxobutanoate, and friends who are interested can also refer to it.

Reference:
Patent; Qianhui Pharmaceutical (Anhui) Co., Ltd.; Yang Huilai; Mao Jie; Sun Xuexi; (7 pag.)CN106749187; (2017); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 52351-75-4, name is 6-Methoxyindoline-2,3-dione, 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. Formula: C9H7NO3

General procedure: A sealed tube was charged with isatin 1 (1a 147 mg, 1.0 mmol), ammonia hydrate 2 (25%, 421 mg, 3.0 mmol) and H2O2 (30%, 227 mg, 2.0 mmol) at room temperature, and then solvent DMSO (4 mL) was added. The resulting mixture was stirred at 30 C in a sealed vessel under air after 4 h, then added 50 mL water to the mixture, extracted with CH3COOC2H5 3 times (3 x 50 mL). The extract was washed with 30% NaCl solution (V/V), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (Petroleum ether/Ethyl acetate = 3:1) to yield the desired product 3a as a yellow solid (89% yield).

The synthetic route of 6-Methoxyindoline-2,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Yu-Wei; Zheng, Lei; Jia, Feng-Cheng; Chen, Yun-Feng; Wu, An-Xin; Tetrahedron; vol. 75; 11; (2019); p. 1497 – 1503;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 5181-35-1, 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. 5181-35-1, name is 2-(2-Bromoethoxy)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

Compound VII: Weigh 2.3g o-nitrobenzyl mercaptan (14.2mmol) And 5.73g of N-(2-bromoethoxy)phthalimide (21.3mmOl) in a round bottom flask, Dissolved with 25ml dimethyl sulfoxide, To the reaction solution was added 3ml of triethylamine (21.3mmol), and reacted at room temperature for 4h; TLC monitoring showed that o-nitrobenzyl mercaptan was completely consumed. To the reaction mixture, an appropriate amount of water was added and the mixture was extracted with dichloromethane for 2-3 times. The organic phase was collected, dried over anhydrous sodium sulfate, Separation by column chromatography (RhoEpsilon:EpsilonAlpha = 5:1), 3.74 g of compound VII (N- (2 – ((2-nitrobenzyl) mercapto) ethoxy) phthalimide was obtained as a white solid (73.2% yield). As shown in FIG. 4, FIG. 4 is a nuclear magnetic hydrogen spectrum of the compound YPi11 prepared in this example.

The chemical industry reduces the impact on the environment during synthesis 2-(2-Bromoethoxy)isoindoline-1,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Patent; University of Science and Technology of China; Huang Jianfeng; Shi Jing; Chu Guochao; (21 pag.)CN107698474; (2018); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 5332-26-3, name is 2-(Bromomethyl)isoindoline-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 5332-26-3, category: indolines-derivatives

Example 1 Diphenyl(phthalimidomethyl)phosphine oxide IV Toluene (25 ml) was added to a mixture of ethyl diphenylphosphinite (5 g, 21.71 mmole) and the N-(bromomethy)phthalimide III (5.21 g, 21.70 mmole) at room temperature. The reaction mixture was heated to 90 C. and maintained at this temperature for 48 h when the reaction was complete as indicated from the TLC of the reaction mixture. The reaction mixture was concentrated under reduced pressure, triturated with toluene and filtered to furnish the phosphine oxide compound IV as a solid; yield: 6 g, 76.5%.

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; HELVETICA INDUSTRIES (P) LIMITED; US2011/263870; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem