Category: indolines-derivatives

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. 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, A new synthetic method of this compound is introduced below., HPLC of Formula: C9H6BrNO2

General procedure: A mixture of isatin (0.14 g, 1mmol), 5,5-dimethylcyclohexanedione (0.14 g, 1 mmol), 2-hydroxy-4H-benzo[4,5]thiazolo[3,2-a]pyrimidin-4-one (0.22 g, 1 mmol) and H3PW12O40 (0.06 g, 3 mol%) in dry acetonitrile (5 ml) was refluxed. The reaction progress was monitored by thin-layer chromatography (eluent: ethylacetate/hexane (2:1)). After completion of the reaction, the reaction mixture was cooled to room temperature. Then, the precipitated product was filtered and washed with acetonitrile (10ml). The obtained crude mass was purified by column chromatography over silica gel using ethylacetate/hexane (1:1) as eluent to give the desired product.

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:
Article; Jannati, Saeideh; Esmaeili, Abbas Ali; Tetrahedron; vol. 74; 24; (2018); p. 2967 – 2972;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 39603-24-2, name is 5,7-Dimethylindoline-2,3-dione, molecular formula is C10H9NO2, 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. Product Details of 39603-24-2

General procedure: A mixture of isatins 1c, e-g (1 mmoL) with an equimolar amount of 2-mercaptobenzimidazole6 (0.15 gm, 1 mmoL) and bromoacetic acid 3 (0.14 g, 1 mmoL) in glacial acetic acid (10 mL) in thepresence of sodium acetate (0.16 g, 2 mmoL), was heated under reflux for 2 h. The obtained solid wasfiltered off while hot, washed with hot ethanol, dried and recrystallized from DMF to afford the targethybrids 7a-d.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 39603-24-2, its application will become more common.

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

Adding a certain compound to certain chemical reactions, such as: 18711-13-2, name is 4,7-Dichloroindoline-2,3-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 18711-13-2, Product Details of 18711-13-2

General procedure: To the stirred solution of beta-keto ester 2(aei) (1.0 mmol) and DABCO (30 mol %) in 5 mL THF was added isatin 1(aeh) (1 mmol).The mixture was then stirred at room temperature for stipulated time (5-8 h). After completion of reaction as indicated by TLC, thesolvent was removed at reduced pressure on a BUCHI rotary evaporator. The residue was then purified by column chromatography on silica gel (hexane/ethyl acetate4:1 to 1:1) to afford thedesired product 3(a-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, 4,7-Dichloroindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Thakur, Pramod Bhagwan; Sirisha, Katukuri; Sarma, Akella Venkata Subrahmanya; Nanubolu, Jagadeesh Babu; Meshram, Harshadas Mitaram; Tetrahedron; vol. 69; 31; (2013); p. 6415 – 6423;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 71294-03-6, 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. 71294-03-6 name is 7-Fluoroindolin-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.

7-Fluoro-1,3-dihydro-indol-2-one (7.3 g, 48 mmol) and lithium chloride (6.67 g, 158 mmol) was dissolved in THF (200 mL). The solution was then cooled to -78 C. and n-butyllithium (2.5 M, 40 mL, 100 mmol) was added slowly over a 15 minute period. After 20 minutes at -78 C., methyl iodide (6 mL, 96 mmol) was added and the mixture allowed to warm to room temperature. After 24 hours, the mixture was poured into water and extracted with ethyl acetate, dried (MgSO4), and concentrated in vacuo. Flash chromatography (SiO2, Hexane/ethylacetate 9/1 then 8/2) gave 7-fluoro-3,3-dimethyl-1,3-dihydro-2H-indol-2-one (4.1 g, 48%)

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

Reference:
Patent; Wyeth; US2006/9509; (2006); 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. 6326-79-0, name is 6-Bromoisatin, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 6326-79-0

To a suspension of 6-bromoisatin (Richman) (5.0 g, 22.1 mmol) in water (55 ml) was added [NAOH] (0.94 g, 23.5 mmol, 1.1 equiv) and the mixture was warmed to approximately [35 C] for 30 minutes to form a solution. The solution was cooled to [5 C] and a solution of sodium nitrite (1.70 g, 24.8 mmol, [1.] [1] equiv) was added dropwise over approximately 30 minutes, keeping the temperature below 10 C. The whole mixture was added dropwise via a cannula to a vigorously stirred solution of concentrated sulphuric acid (4.48 g, 45.7 mmol, 2.0 equiv) in water (55 ml) keeping the temperature below [10 C.] The mixture was stirred for 20 minutes and a solution of tin (II) chloride (10.2 g, 54.0 mmol, 2.4 equiv) in concentrated hydrochloric acid (21 ml) was added dropwise. The mixture was stirred at [5 C] for 2 hours and the resulting crude 5-methylindazole-3-carboxylic acid was isolated by filtration and washed several times with water. The yellow solid was then azeotroped with toluene (3 x 100 ml) to remove water prior to the next step to leave a yellow/green solid. LCMS MH+ 238/240 [(79BR/8LBR),] RT 2.69 min.

According to the analysis of related databases, 6326-79-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTEX TECHNOLOGY LIMITED; WO2004/14864; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 16800-68-3, name is 1-Acetylindolin-3-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. SDS of cas: 16800-68-3

3 -propyl-propyne acid 4 – nitrophenyl-unitz (69.3 mg 0.3 mmol), was used. 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 3h 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, 36 mg and gave rise 92% to unit_.

The synthetic route of 1-Acetylindolin-3-one has been constantly updated, and we look forward to future research findings.

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

Reference 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.

General procedure: To a 25 mL round bottomed flask was added different substituted oxindoles 8 (0.2 mmol, 1.0 equiv.) and bromoethylsulfonium salt 9 (132.99 mg, 0.3 mmol, 1.5 equiv.), DMF (2 mL). The mixture was stirred at room temperature for 5min and Et3N (61.88 mg, 0.6 mmol, 3.0 equiv.) was added into reaction system. The mixture was stirred for 6h at room temperature until the reaction completed, quenched with saturated ammonium chloride solution (5 mL), and was extracted with EtOAc (3×30 mL). The combined organic layer washed with H2O (2×10 mL), dried with anhydrous sodium sulfate. After concentration, product was purified using column chromatography on silica gel with suitable eluent. Spiro[cyclopropane-1,3?-indoline]-2?-one (10a). Colorless crystalline (24 mg, 75 % yield). mp 177 – 180 C. Analytical data for 10a was consistent with that previously reported [10h]. 1H NMR (300 MHz, CDCl3): delta 8.94 (s, 1H), 7.16 – 7.26 (m, 1H), 6.97 – 7.00 (m, 2H), 6.84 (d, J=7.4Hz, 1H), 1.75 – 1.79 (m, 2H), 1.52 – 1.56 (m, 2H); delta13C NMR (75 MHz, CDCl3): delta 179.8, 140.8, 131.3, 126.8, 122.0, 118.6, 109.9, 27.6, 19.5. HRMS (ESI-TOF) calcd for C10H10NO [M+H] +: 160.0757; found: 160.0757.

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:
Article; Qin, Hui; Miao, Yuanyuan; Zhang, Ke; Xu, Jian; Sun, Haopeng; Liu, Wenyuan; Feng, Feng; Qu, Wei; Tetrahedron; vol. 74; 47; (2018); p. 6809 – 6814;,
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. 18711-13-2, name is 4,7-Dichloroindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 4,7-Dichloroindoline-2,3-dione

A. Synthesis of 4,7-dichloro-1-pentyl-1H-indole-2,3-dione To a mixture of sodium hydride (0.17 g, 6.94 mmol, 60% dispersion in mineral oil) in anhydrous N,N-dimethylformamide (5.00 mL) was added a solution of 4,7-dichloro-1H-indole-2,3-dione (1.00 g, 4.60 mmol) in N,N-dimethylformamide (5.00 mL) at 0 C. The brown reaction mixture was stirred for 0.5 h followed by the addition of a solution of 1-bromopentane (0.84 g, 5.55 mmol) in anhydrous N,N-dimethylformamide (5.00 mL). The reaction mixture was stirred at ambient temperature for 16 h and poured into wet ethyl ether (30.0 mL). After the organic layer was separated, it was washed with water (2*20.0 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to dryness. The gummy residue was dried under vacuum and the solid was triturated with ether to give the title compound (0.98 g, 98%): MS (ES+) m/z 286.2 (M+1).

According to the analysis of related databases, 18711-13-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; XENON PHARMACEUTICALS INC.; US2010/173967; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 2058-72-2, name is 5-Bromo-1-methylindoline-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. Recommanded Product: 2058-72-2

General procedure: A mixture of corresponding compound 1(0.5 mmol), isatin 3 (0.5 mmol), and sarcosine (0.5 mmol) in acetonitrile (40 mL) (for 1a-c) or in amixture of acetonitrile (30 mL) and chloroform (10 ml) (for 1d-f) was refluxed with stirring for 36 or 72 h for starting compounds 1a-c and 1d-f, respectively. Then the reaction mixture was cooled to room temperature, the precipitate of compounds 4a-e,j,o was filtered off and washed with acetonitrile and water. The reaction mixture of compounds 4f-i,k-n,p-t was concentrated on a rotary evaporator to half of an original volume. After cooling, the precipitate was filtered off and washed with water. Recrystallization from acetonitrile or methanol (4n) gave dispirocompounds 4a-t.

The synthetic route of 5-Bromo-1-methylindoline-2,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Izmest’ev, Alexei N.; Gazieva, Galina A.; Sigay, Natalya V.; Serkov, Sergei A.; Karnoukhova, Valentina A.; Kachala, Vadim V.; Shashkov, Alexander S.; Zanin, Igor E.; Kravchenko, Angelina N.; Makhova, Nina N.; Beilstein Journal of Organic Chemistry; vol. 12; (2016); p. 2240 – 2249;,
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. 14192-26-8, name is Methyl 2-oxoindoline-6-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C10H9NO3

Methyl oxindole-6-carboxylate (300.0 g / 1.5691 mol) was suspended in toluene (900.0 ml) at ambient temperature. Chloroacetic anhydride (282.27 ml / 1.494 eq) was added and the suspension was stirred at reflux for 4 hours. The suspension was cooled to ambient temperature, stirred for 30 minutes and the crystalline product filtered off. The crude product was washed with methyl cyclohexane, ice-cold MeOH and Et20 and dried in vacuum to obtain 358.1 g (85.3 %) of l-(2-chloro-acetyl)-2-oxo-2,3-dihydro-lH-indole-6-carboxylic acid methyl ester.

According to the analysis of related databases, 14192-26-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; RATIOPHARM GMBH; TEVA PHARMACEUTICALS USA, INC.; ALBRECHT, Wolfgang; FISCHER, Dirk; JANSSEN, Christian; WO2012/68441; (2012); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem