Month: February 2021

Adding a certain compound to certain chemical reactions, such as: 446292-08-6, name is (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)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 446292-08-6, Computed Properties of C22H19N3O6

5L three-necked flask with a compound of formula (II)(100, (^, 24011111101),Anhydrous ethanol 6001111 (6ml / g), stirring, suspended state,Room temperature dropMethylamine solution(40% aqueous solution, 56 g, 720 mmo 1),The reaction system gradually heated to 60 ~ 63 C, keep the temperature stirring for 2 hours,(20 ~ 25 C), suction filter, filter cake methanol washing, drying and drying for 6 hours, to give the formula (20 ~ 25 C), and then cooled to 55 C, III) hydrochloride of the structural compound in a yield of 85%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione, and friends who are interested can also refer to it.

Reference:
Patent; SHENZHEN HYBIO PHARMACEUTICAL CO., LTD.; YUAN, HUIXING; XIAO, QING; LI, GUOTAO; MA, YAPING; YUAN, JIANCHENG; (21 pag.)CN104016975; (2017); B;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 611-09-6, These common heterocyclic compound, 611-09-6, name is 5-Nitroindoline-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.

General procedure: First, 0.01g of the CoFe2O4(at)SiO2(at)SO3H was dispersed for 30min and after that an amount of 1mmol from isatin, malononitrile and dimedone with ethanol/water (ratio 1:1) were mixed, and the final mixture was placed in 80C at the reflux condition. After completing the reaction by passing a certain time, the con -taining solution was separated by centrifuging and the crude product extracted and washed with ethyl acetate, and then Na 2 SO 4 was added to dehydrating the product. After that, the solvent was removed by using a rotary evaporator and finally the product recrystallized in hot ethanol to gain the pure product. Moreo -ver, the catalyst was washed and applied for several times to examine reusability. Structural assignments of the products are based on their 1 HNMR, 13 CNMR and IR spectra.

Statistics shows that 5-Nitroindoline-2,3-dione is playing an increasingly important role. we look forward to future research findings about 611-09-6.

Reference:
Article; Zamani-Ranjbar-Garmroodi, Bardia; Nasseri, Mohammad A.; Allahresani, Ali; Hemmat, Kaveh; Research on Chemical Intermediates; vol. 45; 11; (2019); p. 5665 – 5680;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 1074-82-4, 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 1074-82-4 as follows.

To a stirred solution of 1,5-dibromopentane (13-k) (170.58 mL, 1.26 mol) in DMF (1.5 L) was added potassium phthalate (12-k) (78.0 g, 0.42 mol) portion-wise over 30 min at room temperature. After complete addition, the reaction mixture was stirred at 90C for 18 h, then quenched with water (3 L) and extracted with diethyl ether (500 mL x 4). The combined organic extracts were washed with water (500 mL x 2), followed by brine (500 mL x 2) and dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to obtain the crude. The residue was purified by silica gel column chromatography (60-120 mesh) using 5-10% EtOAc / hexanes to afford 14-k as an off-white solid (81 g, 65% yield). 1H NMR (400 MHz, CDC13): delta 7.82 (dd, J= 5.5, 3.1 Hz, 2H), 7.69 (dd, J= 5.5, 3.0 Hz, 2H), 3.68 (t, J= 7.2 Hz, 2H), 3.38 (t, J= 6.8 Hz, 2H), 1.93-1.85 (m, 2H), 1.70 (p, J= 7.5 Hz, 2H), 1.53-1.43 (m, 2H).

According to the analysis of related databases, 1074-82-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CV6 THERAPEUTICS (NI) LIMITED; SPYVEE, Mark; (500 pag.)WO2018/98206; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 3485-84-5, name is N-Vinylphthalimide, molecular formula is C10H7NO2, 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. Quality Control of N-Vinylphthalimide

Step 2: Preparation of 4-{3-[(E)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)vinyl]-phenoxy}-N-methylpyridine-2-carboxamide To a degassed solution of solution 4-(3-iodophenoxy)-N-methylpyridine-2-carboxamide (11.4 g, 32.4 mmol) in anhydrous DMF (100 mL) was added palladium acetate (0.15 g, 0.65 mmol), tri-o-tolylphosphine (0.79 g, 2.58 mmol), 2-vinyl-1H-isoindole-1,3(2H)-dione (5.60 g, 32.4 mmol), and DIPEA (11.5 mL 64.5 mmol). After degassing the mixture again, the reaction was heated at 90 C. overnight under nitrogen. The reaction mixture was then cooled to rt and concentrated. The mixture was diluted with water and extracted with DCM (2*). The organic solutions were combined and washed with brine, dried over Na2SO4, filtered, and concentrated. The residue was purified by column chromatography to give 4-{3-[(E)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)vinyl]-phenoxy)-N-methylpyridine-2-carboxamide (8.9 g, 69%) as a yellow solid. 1H NMR (300 MHz, CDCl3) delta: 8.40 (d, 1H), 7.96-8.05 (m, 1H), 7.89-7.94 (m, 2H), 7.73-7.80 (m, 3H), 7.65 (d, 1H), 7.33-7.44 (m, 3H), 7.20 (t, 1H), 6.96-7.01 (m, 2H), and 3.01 (d, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3485-84-5, its application will become more common.

Reference:
Patent; Millennium Pharmaceuticals, Inc.; US2008/64729; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 132898-96-5, name is 2,3-Dioxoindoline-5-sulfonyl chloride, 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 132898-96-5, category: indolines-derivatives

T he hydrochloride salt of 3,3-difluoropyrrolidine (475 mg, 3,3 mmol) ^as added to a solution of2.3-dioxoiotando.me-5-suifonyl chloride (1 ,0 g, 4, 1 mmol) and diisopropyleth) 1 amine (2 0 ml, 12 mmol) in 1 : 1 CH2Cl2ZTHF (40 mL) at -50 C. The solution was warmed to room temperature and stirred at that temperature for 12 hours The reaction mixture was then concentrated, dissolved in CH2Cl2. and washed with saturated NaHCOj and brine. The organic layer was dried (MgSO4), filtered, concentrated, and purified by flash chromatography on silica gel (5% MeOH in CH2Cl2) to provide 575 mg of the product as an orange 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, 2,3-Dioxoindoline-5-sulfonyl chloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; WYETH LLC (FORMERLY KNOWN AS WYETH); DOLLINGS, Paul, Jeffrey; DONNELL, Andrew, Forrest; GILBERT, Adam, Matthew; ZHANG, Minsheng; HARRISON, Boyd, Lynn; STANTON III, Charles, John; O’NEIL, Steven, Victor; HAVRAN, Lisa, Marie; CHONG, Dan, Chaekoo; WO2010/77839; (2010); A1;,
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 875003-43-3 as follows. Application In Synthesis of 7-Fluoro-1-methylindoline-2,3-dione

Step 1b: Preparation of 7-fluoro-1-methyl-1,3-dihydro-indol-2-one (7); 7-Fluoro-1-methyl-1H-indole-2,3-dione (6, 2.48 g, 0.0138 mol) is heated with neat hydrazine hydrate (30 ml) at 130 C. for 30 minutes. The mixture is cooled, diluted with ice water and extracted with ethyl acetate. The extract is washed with brine, dried (Na2SO4), and evaporated to give the title compound as a solid. HPLC r.t. 4.07 min; MS for C9H8FNO m/z 165.16 (M+H)+.

According to the analysis of related databases, 875003-43-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Josyula, Vara Prasad Venkata Nagendra; Gordeev, Mikhail; Luehr, Gary; US2006/229349; (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. 603-62-3, name is 3-Nitrophthalimide, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 3-Nitrophthalimide

Example 4; Preparation of 3-Nitro-N-ethoxycarbonyl-phthalimide According to Scheme D; Ethyl chloroformate (1.89 g, 19.7 mmol) was added dropwise over 10 minutes to a stirred solution of 3-nitrophthalimide (3.0 g, 15.6 mmol) and triethylamine (1.78 g, 17.6 mmol) in DMF (20 mL) at about 0-5 C. under nitrogen. The reaction was allowed to warm to room temperature and stirred for 4 hours. The reaction mixture was slowly added to an agitated mixture of ice and water (60 mL). The slurry was filtered and the solid was crystallized from CHCl3 (15 mL) and petroleum ether (15 mL) to yield 3.1 g (75%) of the product as an off-white solid: mp 100.0-100.5 C.; 1H NMR (CDCl3) delta 8.25(d, J=7.5 Hz, 1 H), 8.20(d, J=8.0 Hz, 1 H), 8.03(t, J=7.9 Hz, 1 H), 4.49(q, J=7.1 Hz, 2 H), 1.44(t, J=7.2 Hz, 3 H); 13C NMR (CDCl3) delta 161.45, 158.40, 147.52, 145.65, 136.60, 132.93, 129.65, 128.01, 122.54, 64.64, 13.92; HPLC, Waters Nova-Pak/C18, 3.9¡Á150 mm, 4 micron, 1 mL/min, 240 nm, 30/70 CH3CN/0.1% H3PO4(aq), 5.17 min (98.11%); Anal. calculated for C11H8N2O6: C, 50.00; H, 3.05; N, 10.60. Found: C, 50.13; H, 2.96; N, 10.54.

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 603-62-3.

Reference:
Patent; Celgene Corporation an orgnization of the state New Jersey; US2007/4920; (2007); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 56341-37-8, name is 6-Chlorooxindole, 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 56341-37-8, SDS of cas: 56341-37-8

To a solution of 6-chlorooxiindole (5.0 g, 29.8 mmol) in acetonitrile (50 mL) at 10C, NBS (5.8 g, 32.8 mmol) was added. The reaction mixture was stirred at room temperature for 3 h. The reaction was monitored by LC-MS. The reaction mixturewas evaporated to dryness and extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried over anhydrous Na2SO4 and concentrated. This was further purified by trituration with n-hexane to yield title compound (7.0 g, 95.8%) as a brown solid. LCMS: (M-H) = 244.9; 1H NMR: (DMSO-d6, 300MHz) 610.61(s, 1H), 7.56(s, 1H), 6.98(s, 1H), 3.51(s, 2H).

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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; MADANAHALLI RANGANATH RAO, Jagannath; GURRAM RANGA, Madhavan; PACHIYAPPAN, Shanmugam; WO2014/202528; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 17564-64-6, name is 2-(Chloromethyl)isoindoline-1,3-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. Computed Properties of C9H6ClNO2

The N,Se acetal 5 was prepared by a slight and safer modification of the original procedure4 where, the required phenylselenol intermediate was replaced by sodium phenylselenolate. In a 50 mL three-neck flask equipped with a reflux condenser were placed diphenyl diselenide (0.63 g, 2 mmol) and 16 mL of dry DMF. The solution was heated at 60 C and stirred rapidly under nitrogen while NaBH4 (0.15 g, 4 mmol) was added portionwise. Hydrogen was evolved and the reaction mixture turned colorless and homogeneous upon complete reduction of the selenide. The reaction was heated at 110 C for 1 h and then cooled to room temperature. Solid N-chloromethylphthalimide (0.78 g, 4 mmol) was added to the orange solution. After stirring at room temperature for 12 h, 2 N aqueous hydrochloric acid (10 mL) was added carefully to the white suspension. The entire product mixture was poured into 50 mL of water and 40 mL of diethyl ether, mixed, and separated. The aqueous phase was extracted with 20 mL of diethyl ether and the combined organic phases were washed with H2O (4 ¡Á 10 mL), 10 mL of brine, dried over sodium sulfate and concentrated. The solid residue was washed with light petroleum (2 ¡Á 10 mL) and dried over P2O5 to afford 5 in 82% yield and with spectral data in good agreement with those reported in the literature.4

The synthetic route of 2-(Chloromethyl)isoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Temperini, Andrea; Minuti, Lucio; Tetrahedron Letters; vol. 53; 22; (2012); p. 2709 – 2711;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 102359-00-2, 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. 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, This compound has unique chemical properties. The synthetic route is as follows.

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.

The chemical industry reduces the impact on the environment during synthesis 2-Oxoindoline-5-carboxylic Acid. I believe this compound will play a more active role in future production and life.

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