Month: September 2021

Application of 954-81-4, These common heterocyclic compound, 954-81-4, name is N-(5-Bromopentyl)phthalimide, 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.

Step A: Preparation of 2-{(S)-1-[5-(1,3-Dioxo-1,3-dihydroisoindol-2-yl)pentyl]pyrrolidin-3-yl}-2,2-diphenylacetamide A 200-mL three-necked flask was charged with 2,2-diphenyl-2-(S)-pyrrolidin-3-ylacetamide, the intermediate from Example A (2.8 g, 10 mmol), N-(5-bromo-pentyl)phthalimide (3.55 g, 12 mmol), triethylamine (4.27 mL, 30 mmol) and ACN (100 mL). The reaction mixture was stirred at 55 C. for 8 hours and then concentrated under reduced pressure. IPAc was added to the residue and this mixture was washed with 0.5 N NaOH (2*100 mL), brine (1*100 mL), dried over magnesium sulfate, filtered and concentrated to give 5 g of the title intermediate (100% yield). MS m/z [M+H+] calc’d for C31H33N3O3 496.3; found 496.4.

Statistics shows that N-(5-Bromopentyl)phthalimide is playing an increasingly important role. we look forward to future research findings about 954-81-4.

Reference:
Patent; Theravance, Inc.; US2005/203161; (2005); A1;,
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Reference of 923590-95-8,Some common heterocyclic compound, 923590-95-8, name is 4-Bromoisoindoline hydrochloride, molecular formula is C8H9BrClN, 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.

Adding a sodium hydroxide solution to the solution containing Compound I, And extracted with dichloromethane, Add Boc 2 O dropwise, react overnight, add water, separate dichloromethane, wash twice with saturated sodium chloride, dry over anhydrous sodium sulfate, concentrate, separate and purify by column chromatography, use 100-200 mesh silica gel column, wash Deionization using PE (petroleum ether): EA (ethyl acetate) = 40:1-20:1, to give an off-white solid 45g.

The synthetic route of 923590-95-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nanjing Xiaozhuang College; Shanghai Weifenqi Pharmaceutical Technology Co., Ltd.; Zhu Yuan; Wu Longzhong; Li Jianxiang; Yuan Yanfen; (11 pag.)CN109678787; (2019); A;,
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Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 324-03-8, name is 6-Fluoroindoline-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 324-03-8, Safety of 6-Fluoroindoline-2,3-dione

To a mixture of 5.0 g (30.3 mmol) 6-fluoro-1H-indole-2,3-dione in 75 mL of 33% aq. potassium hydroxide solution was added 4.67 g (53.0 mmol) pyruvic acid and this mixture was heated at 40C for 18 hours. After cooling to room temperature 10% aq. sulfuric acid was added (pH about 1). The formed solid was isolated by filtration and dried in vacuum. The solid was the desired 7-fluoroquinoline-2,4-dicarboxylic acid,which was used without further purification. Yield: 6.02 g (85%).1H-NMR (300 MHz, DMSO d6) 6 (ppm) = 7.78 (ddd, 1H), 7.99 (dd, 1H), 8.42 (s, 1H),8.89 (dd, 1H).

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; BAYER PHARMA AKTIENGESELLSCHAFT; HEISLER, Iring; BUCHMANN, Bernd; CLEVE, Arwed; HEROULT, Melanie; NEUHAUS, Roland; PETRUL, Heike; QUANZ-SCHOeFFEL, Maria; KOPITZ, Charlotte Christine; (285 pag.)WO2016/202935; (2016); A1;,
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Indoline | C8H9N – PubChem

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. SDS of cas: 102359-00-2

Ethyl chloroformate and TEA were added to a THF solution of 2-oxoindoline-5-carboxylic acid and stirred. The reaction solution was mixed with N,N-diethylethylenediamine, stirred and then purified to obtain N-[(2-diethylamino)ethyl]-2-oxoindoline-5-carboxamide as a brown solid. F+: 276.

The synthetic route of 2-Oxoindoline-5-carboxylic Acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; YAMANOUCHI PHARMACEUTICAL CO. LTD.; EP1396490; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 868066-91-5, These common heterocyclic compound, 868066-91-5, name is 5-Bromo-2-methylisoindolin-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.

[00532] Intermediate Sic: 2-methyl-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yI)isoindolin-1-one[00533] A round bottomed flask containing bis(pinacolato)diboron (354mg, 1 .3gmmol) and KOAc (326mg, 3.32mmol) in 1 ,4-dioxane (6.5mL) was evacuated/backfilled with nitrogen. Pd(dppt)C12.CH2CI2 (54mg, 0.O7mmol) was added and the flask was evacuated/backfilled with nitrogen again. The reaction mixture was then stirred and heated at 85 C overnight. After this timethe mixture was cooled to room temperature, filtered through a plug of celite and the solid was washed with EtOAc. The filtrate was concentrated and the residue purified by column chromatography using an eluent of 0-100% EtOAc in heptane to give 2-methyl-5-(4,4,5,5- tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-one (324mg,1.lgmmol, 89% yield) as a brown solid.1H NMR (CDCI3, 400MHz) O/ppm: 7.92 (1H, dd, J= 7.6Hz, 0.4Hz), 7.90-7.89 (1H, m), 7.85 (1H, dd, J 7.6Hz, 0.4Hz), 4.39 (2H, 5), 3.23 (3H, 5), 1.38 (12H, 5).MS Method 3: RT: 3.61 mi m/z 274.1 [M+H]

The synthetic route of 868066-91-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; REDX PHARMA PLC; ARMER, Richard; BELFIELD, Andrew; BINGHAM, Matilda; JOHNSON, Alice; MARGATHE, Jean-Francois; AVERY, Craig; HUGHES, Shaun; MORRISON, Angus; (278 pag.)WO2016/51193; (2016); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 6341-92-0, 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. 6341-92-0, name is 6-Chloroisatin belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A mixture of isatin 1 (1.0 mmol), malononitrile or cyanoacetic ester 2 (1.0 mmol), phthalhydrazide (1.0 mmol), and NiCl2 (0.2 mmol) in PEG 600 (5 mL) was stirred at 100 C for the appropriate time (refPreviewPlaceHolderTable 2). After complete conversion as indicated by TLC, water was added and the product was extracted with ethyl acetate (2×10 ml). The organic phase was dried over anhydrous Na2SO4, and concentrated under reduced pressure. The crude product was recrystallized from ethanol to afford the pure product.

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

Reference:
Article; Zhang, Xiao-Nan; Li, Yong-Xiao; Zhang, Zhan-Hui; Tetrahedron; vol. 67; 38; (2011); p. 7426 – 7430;,
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Adding a certain compound to certain chemical reactions, such as: 667463-64-1, name is 6-Bromo-1-methylindoline-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 667463-64-1, COA of Formula: C9H6BrNO2

I-3.1 (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 HCl. The organic layer is dried over MgSO4 and concentrated. The crystallized residue is dissolved in DCM, methanol is added and the DCM is removed in vacuo. The crystallized product is filtered by sunction and washed with cold methanol. Yield 63%, m/z 226/228 [M+H]+, rt 1.16 min, LC-MS Method V001-003.

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, 6-Bromo-1-methylindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GRAUERT, Matthias; ANDERSKEWITZ, Ralf; GRUNDL, Marc; OOST, Thorsten; PAUTSCH, Alexander; PETERS, Stefan; US2014/275155; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 32692-19-6, 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. 32692-19-6, name is 5-Nitroindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A solution of 3-chloromethyl-benzoyl chloride Compound 1b (11.5 g, 0.06 mol) in DCM (25 mL) was added dropwise to a cooled (-60 C.) solution of 5-nitro-2,3-dihydro-1H-indole Compound 1a (10 g, 0.06 mol) in DCM (200 mL) and TEA (10 mL, 0.07 mol). The reaction mixture was warmed to room temperature and stirred for 5 hrs. The mixture was poured into cold water and the organic layer was separated, washed with brine, dried (Na2SO4) and concentrated in vacuo to give the (3-chloromethyl-phenyl)-(5-nitro-2,3-dihydro-indol-1-yl)-methanone Compound 1c (20.69 g, >100%) as a light yellow solid which contained residual DCM.

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

Reference:
Patent; Baxter, Ellen W.; Nortey, Samuel O.; Reitz, Allen B.; Pulito, Virginia L.; Middleton, Steven A.; US2006/183902; (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. 6341-92-0, name is 6-Chloroisatin, This compound has unique chemical properties. The synthetic route is as follows., name: 6-Chloroisatin

General procedure: A 25-mL flask, equipped with a magnetic stirring bar, was charged with 2-(1,3-dithiolan-2- ylidene)acetonitrile 1a (143 mg, 1.0 mmol), isatin 2a (74 mg, 0.5 mmol), and MeCN (3.0 mL), followed by addition of a solution of I2 (25 mg, 0.1 mmol) in MeCN (1.0 mL). The reaction mixture was stirred at 80 C for 12 h. After 1a was consumed, as indicated by TLC, the reaction mixture was quenched with saturated aqueous Na2S2O3 (1.0 mL) and water (20.0 mL), and stirred for another 10 min. The fully precipitated solid was filtered and washed with water (20.0 mL). Then it was further washed with petroleum ether-ethyl acetate (1/1, V/V, 20.0 mL) and dried under vacuum to afford 3a.

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 6341-92-0.

Reference:
Article; Liang, Deqiang; Li, Xiangguang; Yang, Juan; Li, Yanni; Wang, Baoling; Cheng, Ping; Synthetic Communications; vol. 46; 23; (2016); p. 1924 – 1931;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 17702-83-9,Some common heterocyclic compound, 17702-83-9, name is 2-(8-Bromooctyl)isoindoline-1,3-dione, molecular formula is C16H20BrNO2, 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: 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.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(8-Bromooctyl)isoindoline-1,3-dione, its application will become more common.

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