Category: indolines-derivatives

Adding a certain compound to certain chemical reactions, such as: 201940-08-1, name is tert-Butyl 5-bromoisoindoline-2-carboxylate, 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 201940-08-1, Computed Properties of C13H16BrNO2

Example 3-91 a 2,3-Dihydro-1H-isoindole-5-carboxylic acid methyl ester was synthesised according to the following scheme: A mixture of 5-bromo-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester (200 mg, 0.67 mmol), Pd(OAc)2 (30 mg, 0.2 equiv), DPPP (55 mg, 0.2 equiv), TEA (0.93 mL, 10 equiv) and MeOH:DMSO (1:1, 4 mL) was stirred for 16 h under CO (balloon) at 80 C. LC-MS and TLC (20% EtOAc-Hexane) showed completion of the reaction. The Reaction mixture was concentrated to remove MeOH and diluted with EtOAc (10 mL), and washed with water (2*25 mL). The organic layer was dried (Na2SO4), concentrated and purified by silica gel column chromatography (eluent=20% EtOAc-Hexane), giving pure 1,3-dihydro-isoindole-2,5-dicarboxylic acid 2-tert-butyl ester 5-methyl ester (150 mg, 81%). MS (APCI+): m/z 178.1 (MH+-Boc).

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, tert-Butyl 5-bromoisoindoline-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Blatt, Lawrence M.; Andrews, Steven W.; Condroski, Kevin R.; Doherty, George A.; Jiang, Yutong; Josey, John A.; Kennedy, April L.; Madduru, Machender R.; Stengel, Peter J.; Wenglowsky, Steven M.; Woodard, Benjamin T.; Woodard, Laura; US2005/267018; (2005); A1;,
Indoline – Wikipedia,
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Synthetic Route of 6780-38-7,Some common heterocyclic compound, 6780-38-7, name is 2-(1,3-Dioxoisoindolin-2-yl)acetyl chloride, molecular formula is C10H6ClNO3, 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.

271 g of water was put in a 1 L four-necked flask and cooled to 10 C. 7 7 g (570.4 mmol) of potassium carbonate was added thereto and dissolved. This was cooled to 3 C. and 30.1 g (223.2 mmol) of 2,2,2-trifluoroethylamine hydrochloride was added thereto. The solution was stirred at 3 C. for 10 minutes, and a solution of 50 g (223.2 mmol) of phthaloylglycyl chloride dissolved in 150.7 g of acetonitrile was added dropwise thereto at such a rate that the reaction solution kept at 20 C. or lower. After stirring for 1 hour, the product precipitated in the reaction was filtered and washed with 150.7 g of water. The obtained solid was dried under reduced pressure at 60 C. to obtain 2-phthaloyl-N- (2,2,2-trifluoroethyl) acetamide as a white solid. The yield was 59.7 g, and the yield was 93.5%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(1,3-Dioxoisoindolin-2-yl)acetyl chloride, its application will become more common.

Reference:
Patent; Nissan Chemical Industries, Ltd.; Moriyama, yuji; (16 pag.)JP5652628; (2015); B2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 611-09-6, 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. 611-09-6 name is 5-Nitroindoline-2,3-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.

General procedure: A mixture of an isatin (1mmol), molononitrile (1mmol), CH activatedacid (1mmol), and [C4(DABCO)2]·2OH(2mol%) inwater (3mL)was stirred at 80 C. The reaction progress was monitored by TLC [eluent:n-hexane:EtOAc (9:2)] (It is important to that by beginning of thereaction the products were precipitated in the reaction medium).After completion of the reaction, the mixture was cooled to room temperature and the solid product was filtered, washed with cold distilledwater (2 mL) to obtain essentially pure products. The solid productswere recrystallized from ethanol if necessary.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Nitroindoline-2,3-dione, and friends who are interested can also refer to it.

Reference:
Article; Goli-Jolodar, Omid; Shirini, Farhad; Seddighi, Mohadeseh; Journal of Molecular Liquids; vol. 224; (2016); p. 1092 – 1101;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 39603-24-2, 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. 39603-24-2 name is 5,7-Dimethylindoline-2,3-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.

General procedure: A mixture of isatins 1a-g (1 mmoL) with an equimolar amount of N,N’-diphenyl/(p-tolyl)thiourea2a,b (1 mmoL) and bromoacetic acid 3 (0.14 g, 1 mmoL) in glacial acetic acid (10 mL) in the presenceof sodium acetate (0.16 gm, 2 mmoL), was heated under reflux for 3 h. The formed solid was filteredoff while hot, washed with hot ethanol, dried and recrystallized from DMF to furnish the targethybrids 4a-n.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5,7-Dimethylindoline-2,3-dione, and friends who are interested can also refer to it.

Reference:
Article; El-Naggar, Mohamed; Eldehna, Wagdy M.; Almahli, Hadia; Elgez, Amr; Fares, Mohamed; Elaasser, Mahmoud M.; Abdel-Aziz, Hatem A.; Molecules; vol. 23; 6; (2018);,
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. 16800-68-3, name is 1-Acetylindolin-3-one, This compound has unique chemical properties. The synthetic route is as follows., Safety of 1-Acetylindolin-3-one

3 – (3 – Methylphenyl) propyne acid 4 – nitrophenyl-unitz (84.3 mg 0.3 mmol), was obtained. N- Acetylindole -3 -unitz 26.3 mg (0.15 mmol), the carbene-unitz (0.015 mmol), 3.96 mg, 1 diazabicycloundecene 8 – (-7 -) and methylene-methylene chloride shown in Formula 45 mul IV 0.3 mmol were placed in 3 ml a 25 ml unitunito-two-port 2h bottle, and reacted 30 C, under unituniteous conditions, and concentrated, under inert atmosphere protection, unitant-like conditions. The eluate fractions of all the products 10:1 detected were collected by chromatography with petroleum ether: ethyl acetate in the timetime as eluent column chromatography, and the solvent was evaporated to obtain the residue unit, 45 mg and gave rise 96% to unit_.

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 16800-68-3.

Reference:
Patent; China Pharmaceutical University; Du Ding; Sun Kewen; (10 pag.)CN110156800; (2019); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 20870-79-5, 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. 20870-79-5, name is 5-Nitroindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

5-Amino-2-oxindole 5-Nitro-2-oxindole (6.3 g) was hydrogenated in methanol over 10% palladium on carbon to give 3.0 g (60% yield) of the title compound as a white solid,

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-Nitroindolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sugen, Inc.; US6878733; (2005); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

201940-08-1, name is tert-Butyl 5-bromoisoindoline-2-carboxylate, 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. category: indolines-derivatives

To solution of the aryl bromide (0.200 g, 0.67 mmol) and Pd (PPh3) 4 (39 mg, 0.33 mmol) dissolved in THF under N2 was cannulated the crude vinyl zinc species from step A. The reaction was heated at 50C for 36 hours, and the then filtered through a plug of A1203 with aid of EtOAc and concentrated to give an oil which was used without further purification

The synthetic route of 201940-08-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; INTERMUNE, INC.; ARRAY BIOPHARMA INC.; WO2005/37214; (2005); A2;,
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. 181140-34-1, name is (R)-(-)-N-(2,3-Epoxypropyl)phthalimide, A new synthetic method of this compound is introduced below., category: indolines-derivatives

General procedure: Compounds 3-7 have been synthesized using a procedure originally reported by Roehrig et al.16 Chiral amine or amino alcohol (0.6 mmol, 1.2 equiv) in 10 mL isopropanol was added to the solutionof (R)-N-(2,3-epoxypropyl)phthalimide (102 mg, 0.50 mmol)in 10 mL of isopropanol at in an ice bath and stirred for 1 h. then refluxed for 12 h. The reaction monitored by TLC. Solvent was removed by rotary evaporator under reduced pressure after completion of the reaction.

The synthetic route of 181140-34-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Karakaplan, Mehmet; Jameel, Basam; Tetrahedron Asymmetry; vol. 27; 14-15; (2016); p. 597 – 602;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 4702-13-0, 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. 4702-13-0 name is N-Phthaloylglycine, 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.

STEP A:; To a stirred solution of A/-phthaloylglycine (11.92 g, 58 mmol) indichloromethane (200 mL) at room temperature, oxalyl chloride (7.5 mL, 87mmol) was added. DMF (two drops) was then added. The resulting solutionwas concentrated after stirring four hours at room temperature.Dichloromethane (100 mL, dry) was then added to the residue. Benzylamine(9.5 mL, 87 mmol) was added slowly into the resulting solution. Triethylamine(12 mL, 87 mmol) was then added slowly into the solution. Dichloromethane(200 mL) and methanol (50 mL) were added 30 min after the completedaddition of triethylamine. The resulting solution was extracted with 2 N HCIsolution twice, 1 N NaOH solution one time and 1 N HCI one time, and thendried over MgSO4. The solution was filtered and concentrated to yield N-benzyl-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-acetamide as a white solid.MH+= 294.9.

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

Reference:
Patent; JANSSEN PHARMACEUTICA, N.V.; BAXTER, Ellen; BOYD, Robert; COATS, Steve; JORDAN, Alfonzo; REITZ, Allen; REYNOLDS, Charles H.; SCOTT, MALCOLM; SCHULZ, Mark; DE WINTER, Hans Louis Jos; WO2006/17844; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 7147-90-2,Some common heterocyclic compound, 7147-90-2, name is 5-Chloroisoindoline-1,3-dione, molecular formula is C8H4ClNO2, 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.

General procedure: Phthalimide 6a (148mg, 1mmol), 124 1,4-dibromobutane (1.080g, 5mmol), 12 potassium carbonate (276mg, 2mmol) was added to 115 acetone (3mL), and the reaction mixture was refluxed for 2h. After cooling to room temperature, the reaction mixture was purified by column chromatography using 125 PE: acetone (40:1) as eluent to give 126 7a (260mg, 92%) as a white solid.

The synthetic route of 7147-90-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Xu, Mingshuo; Wang, Yu; Yang, Feipu; Wu, Chunhui; Wang, Zhen; Ye, Bin; Jiang, Xiangrui; Zhao, Qingjie; Li, Jianfeng; Liu, Yongjian; Zhang, Junchi; Tian, Guanghui; He, Yang; Shen, Jingshan; Jiang, Hualiang; European Journal of Medicinal Chemistry; vol. 145; (2018); p. 74 – 85;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem