Month: February 2021

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. 337536-15-9, name is 4-Bromoisoindolin-1-one, A new synthetic method of this compound is introduced below., Product Details of 337536-15-9

EXAMPLE 54A 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-isoindolinone A suspension of Example 1C (10.6 g, 50 mmol) and 4,4,5,5,4′,4′,5′,5′-octamethyl-[2,2′]bi[[1,3,2]dioxaborolanyl] (15.23 g, 60 mmol) in DMF (390 mL) was stirred until a clear yellow solution was obtained. The solution was then treated with potassium acetate (14.72 g, 150 mmol), degassed with nitrogen, treated with [1.1′-bis(diphenylphosphino)-ferrocene]dichloropalladium [II].CH2Cl2 (7 g, 8.5 mmol) and heated to 90 C. overnight. The reaction was cooled to room temperature and filtered through diatomaceous earth (Celite), and concentrated. The concentrate was partitioned between water and ethyl acetate and filtered through diatomaceous earth (Celite). The organic phase was dried (Na2SO4), filtered, and concentrated. The crude product was purified by silica gel chromatography eluding with 100% ethyl acetate and triturated from hexanes to give 4.56 g (35% yield) of the desired product. m.p.: 189-191 C.

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; Curtin, Michael L.; Davidsen, Steven K.; Frey, Robin R.; Heyman, Howard R.; Holms, James H.; Michaelides, Michael; Steinman, Douglas H.; US2005/26976; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 667463-64-1,Some common heterocyclic compound, 667463-64-1, name is 6-Bromo-1-methylindoline-2,3-dione, molecular formula is C9H6BrNO2, 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.

Step 2: Synthesis of Intermediate 1-5.2 1-5.1 (15.0 g, 63 mmol) and hydrazine hydrate (30 mL, 618 mmol) are heated to 125 C for 72 h. To the cool reaction mixture DCM is added and extracted with water and 1 M HC1. The organic layer is dried over MgSO4 and concentrated. The crystallized residue is dissolved in DCM, methanol is added and the DCM is removed under vacuum. The crystallized product is filtered withsunction and washed with cold methanol. Yield 63%, m/z 226/228 [M+H]+, rt 1.16 mi LC-MS Method VOOl 003.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Bromo-1-methylindoline-2,3-dione, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ANDERSKEWITZ, Ralf; GRAUERT, Matthias; GRUNDL, Marc; OOST, Thorsten; PAUTSCH, Alexander; PETERS, Stefan; WO2014/140091; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 21857-45-4, 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. 21857-45-4, name is 5-Methoxyindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 23 alpha-(5-Methoxy-1-indolinyl)-m-tolunitrile An ice cold slurry of 5.89 g (42.6 mmole) of K2 CO3 and 5.3 g (35.5 mmole) of 5-methoxyindoline in 55 ml of DMF was treated dropwise with a solution of 7.28 g (37.3 mmole) of alpha-bromo-m-tolunitrile in 50 ml of DMF. After stirring for 1 hour at room temperature, the reaction mixture was concentrated under high vacuum. The residue was partitioned between methylene chloride (250 ml) and water (250 ml). The organic layer was separated, washed with 5% NaOH (300 ml), brine (300 ml), dried over Na2 SO4 and concentrated under vacuum to yield 9.28 g (98.9% yield) of alpha-(5-methoxy-1-indolinyl)-m-tolunitrile.

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

Reference:
Patent; Hoechst-Roussel Pharmaceuticals, Inc.; US4448784; (1984); A;,
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. 341988-36-1, name is Methyl indoline-6-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., name: Methyl indoline-6-carboxylate

To the solution of methyl ind line~6-carboxyiate (150 mg, 0,85 mmoi) in 5 ml acetone were added K2CO3 (351 mg, 2.54 mmoi) and 3-(triuQromethyl)benzenesuifonyi chloride (271 mu,, 1.69 mmoi). The reaction mixture was stirred at room temperature overnight. The completion of the reaction was monitored by HPLC Upon completion, the solvent was removed in vacuo. The crude product was purified by Combiflash silica gel chromatography (0-20percent of EtOAc in hexarse), which provided 277 mg (85percent) of the title compound as a colorless solid; 1H NMR (400 MHz, CDCis) 5 = 8.25 (d, J – 1.5 Hz, 1 H), 8.12 (s, 1 H), 8.00 (d, J – 8.1 Hz, 1 H), 7.84 (d, J = 7.9 Hz, 1 H), 7,74 (d.d, J =¡¤ 1.4, 7.8 Hz, 1 H), 7.66 – 7.58 (m, 1 H), 7.17 (d, J – 7.9 Hz, 1 H), 4.01 (t, J – 8.6 Hz, 2 H), 3.95 (s, 3 H), 3.00 (t, J ~ 8.6 Hz, 2 H).

According to the analysis of related databases, 341988-36-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THE SCRIPPS RESEARCH INTITUTE; GRIFFIN, Patrick, R.; KAMENECKA, Theodore, M.; DOEBELIN, Christelle; CHANG, Mi, Ra; (109 pag.)WO2018/52903; (2018); 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. 19727-83-4, name is 6-Nitroindoline, This compound has unique chemical properties. The synthetic route is as follows., Formula: C8H8N2O2

1. 1-Cyano-6-nitroindoline To a cooled (4 C.) and stirred solution of 6-nitroindoline (3.04 g) in a mixture of glacial acetic acid (22 ml), water (11 ml) and absolute ethanol (23 ml) was added solid cyanogen bromide (2.93 g) followed by 1N aqueous sodium hydroxide solution (25 ml) over 3 minutes. The mixture was then allowed to warm to room temperature, stirred for a further 21 hours and the solid formed was collected by filtration, washed with water and dried over phosphorous pentoxide to give the title compound (2.94 g) as a solid; deltaH (250 MHz, DMSO-d6) 7.90 (1H, dd, J=8.1 and 2.2 Hz), 7.55-7.50 (2H, m), 4.23 (2H, t, J=8.4 Hz), 3.30 (2H, t, J=8.4 Hz); m/z (CI) 189 (M-).

According to the analysis of related databases, 19727-83-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Merck, Sharp & Dohme Ltd.; US5681833; (1997); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 774-47-0, 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. 774-47-0 name is 5,6-Difluoroindoline-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: To a stirred solution of potassium hydroxide (5 equiv.) in water (4 mL/g) in an ice-water bathwas added the isatin (1 equiv.) portionwise. The reaction mixture was stirred at roomtemperature for 10 minutes, then cooled in an ice-water bath and acetone (4 mL/g) wasadded dropwise. The reaction mixture was stirred in a 70 C heating block for the specifiedtime, then was cooled in an ice-water bath and a solution of aqueous 5 M hydrochloric acidwas added dropwise until the mixture reached pH 5-6. The reaction mixture was stirred atroom temperature for 10 minutes and then filtered. The resultant solid was filtered, driedand purified as specified

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5,6-Difluoroindoline-2,3-dione, and friends who are interested can also refer to it.

Reference:
Article; Lindsay-Scott, Peter J.; Barlow, Helen; Synlett; vol. 27; 10; (2016); p. 1516 – 1520;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 32692-19-6, name is 5-Nitroindoline, 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 32692-19-6, Recommanded Product: 5-Nitroindoline

General procedure: We described the synthesis of the compound 1 (Table 2) to illustrate the general procedure for TFA accelerated Petasis three-component reaction. The descriptions of the preparations of all reported compounds are in the Supporting information section. To a magnetically stirred mixture of 5-nitroindoline (0.164 g, 1.0 mmol), 4-tolyboronic acid (0.135 g, 1.0 mmol), and glyoxylic acid monohydrate (0.092 g, 1.0 mmol) in CH2Cl2 (5 ml) was added TFA (20 mul). The mixture was stirred at room temperature for 4 h. After the completion of the reaction (TLC monitoring), half of the solvent was evaporated by means of a rotovap. The resulting solid was filtered through a sintered glass funnel. The collected solid was thoroughly washed with petroleum ether and a small amount of ice water (5 ml), and then dried in vacuo at room temperature for 24 h to afford 0.26 g (83.3 %) of 2-(5-nitroindolin-1-yl)-2-(p-tolyl) acetic acid as a light yellow solid.

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:
Article; Zhang, Jing; Yun, Fan; Xie, Rui; Cheng, Chunhui; Chen, Guangyao; Li, Jingxuan; Tang, Pingwah; Yuan, Qipeng; Tetrahedron Letters; vol. 57; 35; (2016); p. 3916 – 3919;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 102359-00-2, These common heterocyclic compound, 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, 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.

General procedure: To a solution of 4 (1.77 g, 10 mmol) in 120 mL ofdichloromethane and 10 mL of DMF was added 4-methylmorpholine or DIEA (10 mL), TBTU (4.81 g, 15mmol) and aniline derivatives (11 mmol). The mixture wasstirred under room temperature for 18 h and washed in turnwith 5% sodium carbonate solution, 5% citric acid solutionand saturated sodium chloride solution. After dried byanhydrous sodium sulfate, the organic layer was evaporatedto dryness. The residue was purified with flash chromatography(CH2Cl2:CH3OH, 50:1) to afford intermediates 5a-5l, which were used in the next step in short time. To asolution of compounds 5a-5l (1.0 mmol) in 10 mL methanolwas added piperidine (30 muL) and 1H-pyrrole-2-carbaldehyde/furan-2-carbaldehyde (1.0 mmol). The mixturewas stirred at 60 C for 5 h and cooled to room temperature.After kept in fridge overnight, the target compounds 6a-6land 7a-7l were obtained in high yields.

Statistics shows that 2-Oxoindoline-5-carboxylic Acid is playing an increasingly important role. we look forward to future research findings about 102359-00-2.

Reference:
Article; Ai, Juntao; Lv, Meng; Li, Xiaohui; Chen, Zhuo; Hu, Gaoyun; Li, Qianbin; Medicinal Chemistry Research; vol. 27; 1; (2018); p. 161 – 170;,
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. 59-48-3, name is Indolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Product Details of 59-48-3

5-(Bromo)-1,3-dihydro-indol-2-one A solution of oxindole (2.0 g, 15.0 mmol) and sodium acetate (2.1 g, 25.5 mmol) in CHCl3 (20 cm3) was treated with bromine (2.4 g, 15.0 mmol) in CHCl3 (10 cm3). After 30 min. the mixture was allowed to warm to RT and stirred for 1 h. The reaction mixture was diluted with EtOAc (500 cm3) and poured into water. The aqueous layer was extracted with EtOAc (*2), the combined organic layers were washed with water, sat. sodium hydrogen carbonate solution, brine, dried (MgSO4), and evaporated to give the title compound (3.1 g, 14.6 mmol, 96 %) as an off-white solid which was used without further purification: mp. 221-223 C.; 1H NMR (DMSO-d6) delta3.51 (s, 2H), 6.76 (d, 1H, J=8.1 Hz), 7.33(dd, 1H, J=8.1, 1.7 Hz), 7.37 (s, 1H), 10.49 (br s, 1H); 13C NMR (DMSO-d6) delta36.10 (t), 111.21 (d), 113.16 (s), 127.54 (d), 128.3 (s), 130.40 (d), 143.34 (s), 176.24 (s); MS (EI) m/z 211, 213 (M)+.

The synthetic route of 59-48-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; American Home Products Corporation; Ligand Pharmaceuticals, Inc.; US6391907; (2002); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 2058-72-2, 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. 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A mixture of compound 3 (1 mmol) and the appropriate isatinderivative 4a-i (1 mmol) in absolute ethyl alcohol and catalyticamount of glacial acetic acid was heated under reflux for 4 hrs,filtered while hot and the collected solid was washed with ethanol.The crude products 5a-i were re-crystallized from ethanol/DMFmixture (3:1) to furnish the pure title compounds 5a-i in 43-94%yields.

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

Reference:
Article; Almutairi, Maha S.; Zakaria, Azza S.; Ignasius, P. Primsa; Al-Wabli, Reem I.; Joe, Isaac Hubert; Attia, Mohamed I.; Journal of Molecular Structure; vol. 1153; (2018); p. 333 – 345;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem