Tag: M.W=200-300

Electric Literature of 65435-04-3, 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. 65435-04-3, name is 5-(2-Chloroacetyl)indolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A suspension of 9.3 g 5-chloroacetyl-2-oxindole was stirred in 90 mL pyridine at 80-90 C. for 3 hours then cooled to room temperature. The precipitate was collected by vacuum filtration and washed with 20 mL of ethanol. The solid was dissolved in 90 mL of 2.5 N sodium hydroxide and stirred at 70-80 C. for 3 hours. The mixture was cooled to room temperature and acidified to pH 2 with 0.5 N hydrochloric acid. The precipitate was collected by vacuum filtration and washed thoroughly with water to give crude 5-carboxy-2-oxindole as a dark brown 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-(2-Chloroacetyl)indolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sugen, Inc.; US6395734; (2002); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 181140-34-1, 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. 181140-34-1, name is (R)-(-)-N-(2,3-Epoxypropyl)phthalimide, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Compounds 3-7 have been synthesized using a procedure originallyreported 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. thenrefluxed for 12 h. The reaction monitored by TLC. Solvent was removed by rotary evaporator under reduced pressure after completionof the reaction.

The chemical industry reduces the impact on the environment during synthesis (R)-(-)-N-(2,3-Epoxypropyl)phthalimide. I believe this compound will play a more active role in future production and life.

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

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. SDS of cas: 923590-95-8

Step 4: 1-t-Butyl 2-methyl (2S,4R)-4-(11(4-bromo-1,3-dthydro-2H-isoindol-2-yl)carbonyl]oxy}pyrrolidine-1,2-dicarboicylate To a solution of (2S,4R)-B0C-4-hydroxyproline methyl ester (126.3 g, 515 mmol) in DMF (960 mL) at 0 C. was added N,N’-carbonyldiimidazole (83.51 g, 515 mmol). The reaction mixture was stirred at room temperature for 3 h. 4-Bromoisoindoline hydrochloride (120 g, 515 mmol) and diisopropylethylamine (96.3 mL, 540 mmol) were added and the reaction mixture heated to 50 C. for 6 h then allowed to cool to room temperature and stirred overnight The reaction mixture was partitioned between EtOAc (3 L) and 10% aqueous KHSO4 (6 L), the aqueous re-extracted with EtOAc (2 L) and the combined organic phases washed with 10% aqueous NaHCO3, brine, dried over Na2SO4 and solvent evaporated to a foam (239 g). LRMS (ESI) m/z 471.0 [(M+14)* ; calcd for C20H20BrN2O6: 471.1].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 923590-95-8, its application will become more common.

Reference:
Patent; Gilead Sciences, Inc.; US2010/160403; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 15362-40-0, 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. 15362-40-0, name is 1-(2,6-Dichlorophenyl)-2-indolinone belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: The desired compounds 2(a-d), 3(b-d) and 4(b-d) were procured by subjecting an equivalent mixture of compounds 9 (a-d) (1 mmol) and an active methylene compound- barbituric acid, oxindole and indolinone (1 mmol), respectively in methanol (2 mL) using catalytic amount of piperidine to microwave irradiations at 120 oC for 30 min. The reaction was monitored by TLC after every 10 min. The yellow solid obtained was filtered followed by washing with methanol and dried in air.

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, 1-(2,6-Dichlorophenyl)-2-indolinone, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kaur, Manpreet; Singh, Palwinder; Bioorganic and Medicinal Chemistry Letters; vol. 29; 1; (2019); p. 32 – 35;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 2436-29-5, name is 3-(1,3-Dioxoisoindolin-2-yl)propanal, molecular formula is C11H9NO3, 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. Formula: C11H9NO3

In a 10 ml reaction tube, adding phosphine nitrogen ligand L10a (0.35 mg, 0 . 65 mumol) with the three-phenyl phosphorus is great (0.48 mg, 0 . 50 mumol), system through the vacuum line, replace the nitrogen 3 times, and steams newly added new degassed toluene 2 ml, solution in 90 C under stirring 3 hours, cooling to room temperature, solvent is removed under reduced pressure. At the same time in another 10 ml hydrogenation bottle, adding beta – aminoketone laq (40.6 mg, 0.2 mmol) with anhydrous sodium carbonate (2.12 mg, 0 . 02 mmol), system through the vacuum line, replace the nitrogen 3 times. A syringe has been coordination of the new catalyst for steaming and new degassing of ethanol (3 ml) containing dissolved out and injected into the substrate and additive in the reaction tube, the reaction system is put in an autoclave, in 25 C and H2(50 Bar) is stirred under the condition 24 hours, the solvent is removed under reduced pressure, taking a small amount of the mixed system is nuclear magnetic resonance to determine the conversion rate. The rest of the survivor column chromatography separation, to obtain the pure product 2 aq. The conversion is 100%, enantiomeric excess is 92%. 2 Aq: white solid. According to the embodiment 1 – 12 and not the result of the symmetrical field of catalytic hydrogenation of the well known common sense, can without any doubt be inferred in this embodiment of the product structure is shown in formula (II) of the structure.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2436-29-5, its application will become more common.

Reference:
Patent; Shanghai Jiao Tong University; Shanghai Zizhu Rising Industrial Technology Institute; Zhang Wanbin; Liu Delong; Wang Yanzhao; Jiang Xiuchen; Cao Lingyu; (32 pag.)CN105085372; (2018); B;,
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. 6941-75-9, name is 5-Bromoisoindoline-1,3-dione, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H4BrNO2

Example 38Preparation of ethyl 2-(1-oxo-6-vinylphthalazin-2(1H)-yl)acetate (BI24) Step 1. 5-Bromo-3-hydroxyisoindoline-1-one (BI25); A mixture of Zn powder (1.73 g, 26.154 mmol), copper (II) sulfate pentahydrate (0.02 g, 0.08 mmol) and 2M aq NaOH (27 mL) were cooled to 0 C. 5-Bromoisoindoline-1,3-dione (5 g, 22 mmol) was added at the same temperature over the period of 30 min. The reaction mixture was stirred at 0 C. for 30 min and 3 h at RT. The reaction mixture was filtered and the filtrate was neutralized with concentrated HCl. The reaction mixture was diluted with ethanol and extracted with ethyl acetate. The combined ethyl acetate layer was dried over Na2SO4 and concentrated under reduced pressure to afford the crude title compound as a brown solid, which was used in the next step without further purification (1.3 g): mp 258-261 C.; 1H NMR (400 MHz, DMSO-d6) delta 9.03 (br, 1H), 7.81 (m, 2H), 7.69 (m, 1H), 6.44 (m, 1H), 5.88 (d, J=9.3 Hz, 1H); ESIMS m/z 225.83 ([M-H]-); IR (thin film) 1684, 3246, 606 cm-1.

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; Hunter, James E.; Lo, William C.; Watson, Gerald B.; Patny, Akshay; Gustafson, Gary D.; Pernich, Dan; Brewster, William K.; Camper, Debra L.; Lorsbach, Beth; Loso, Michael R.; Sparks, Thomas C.; Joshi, Hemant; Mandaleswaran, Adiraj; Sanam, Ramadevi; Gundla, Rambabu; Iyer, Pravin S.; US2012/329649; (2012); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 101207-45-8, name is 2-(4-Methylbenzyl)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. COA of Formula: C16H13NO2

Synthesis intermediate 4. Dissolve 12.3g of 2- (4-methylbenzyl) -1H-isoindole-1,3-dione in chloroform, then add 8.7g of chlorosulfonic acid, and react at 80 C for 3h After completion, 15.75 g of Intermediate 4 was obtained after washing with water and removing the solvent, and the yield was 95%.

The synthetic route of 2-(4-Methylbenzyl)isoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhengzhou Shouxing Pharmaceutical Institute Co., Ltd.; Deng Zhaoxi; (13 pag.)CN110483497; (2019); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 129487-92-9, A common heterocyclic compound, 129487-92-9, name is tert-Butyl 5-aminoindoline-1-carboxylate, molecular formula is C13H18N2O2, 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.

Compound 5-aminodihydroindole-1-carboxylic acid tert-butyl ester (200 mg, 0.77 mmol) and 4,6-dichloropyridazine-3-carboxylic acid methyl ester 1a (200 mg, 0.97 mmol) were dissolved in ethanol ( 10mL),It was then heated to 90 C in a sealed tube and stirred for 12 hours.After cooling to room temperature, the solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography (petroleum ether / ethyl acetate = 1/1).The target product 5-((6-chloro-3- (methoxycarbonyl) pyridazin-4-yl) amino) dihydroindole-1-carboxylic acid tert-butyl ester 35a (200 mg, white solid) was obtained,Yield: 58%.

The synthetic route of 129487-92-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Beijing Nuochengjianhua Pharmaceutical Technology Co., Ltd.; Chen Xiangyang; Pang Yucheng; (142 pag.)CN110818641; (2020); A;,
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 3335-98-6 as follows. Quality Control of 1-Phenyloxindole

General procedure: A mixture of isatins (1, 1.0 mmol), indolin-2-ones (2, 1.0 mmol) and ZrCl4 (23 mg, 0.1 mmol) was heated in anhydrous ethanol (5 mL) under reflux. After the disappearance of the reactants (8-12 h, monitored by TLC), the mixture was slowly cooled to room temperature. The red solids precipitated and were collected by filtration, then washed by a small amount of anhydrous ethanol to deliver pure compounds 3.

According to the analysis of related databases, 3335-98-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Liu, Meilin; Qiu, Shaozhong; Ye, Yu; Yin, Guodong; Tetrahedron Letters; vol. 57; 52; (2016); p. 5856 – 5858;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

400727-63-1, name is tert-Butyl 5-nitroisoindoline-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. HPLC of Formula: C13H16N2O4

To a solution of tert-butyl 5-nitroisoindoline-2-carboxylate (1.4) (3.8 g, 14.4 mmol) in MeOH (50 mL) was added 10% Pd/C (380 mg). The suspension was degassed under vacuum and purged with H2 several times. The mixture was stirred under H2 balloon at 50 C overnight. TLC showed the reaction was complete. The suspension was filtered through celite, which was washed three times with MeOH. The combined filtrate was concentrated and the residue was purified by column chromatography (eluted 50% EtOAc in hexanes) to afford tert-butyl 5- aminoisoindoline-2-carboxylate (1.5) (3.1 g, 92.2 %). [00327] LCMS: 235.3[M+1]+.

The synthetic route of 400727-63-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CELGENE AVILOMICS RESEARCH, INC.; SCHWARTZ, C., Eric; SURAPANENI, Sekhar, S.; WORM, Karin Irmgard; (266 pag.)WO2016/90079; (2016); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem