Month: August 2021

Application of 1336963-95-1,Some common heterocyclic compound, 1336963-95-1, name is 6-Bromo-7-fluoroindoline-2,3-dione, molecular formula is C8H3BrFNO2, 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.

2-Amino-4-bromo-3-fluorobenzoic acid To a solution of 6-bromo-7-fluoroindoline-2,3-dione (1.41 g, 5.80 mmol) in 2 N NaOH (15 mL) was added H2O2(30%, 3 mL) at 0 C., the mixture was stirred at 0 C. for 30 min. After stirring at rt for 16 h, the mixture was poured into ice water, the solution was acidified with Conc. HCl, the precipitate was filtered and dried in the air to afford the desired product as a white solid (1.2 g, 89% yield).

The synthetic route of 1336963-95-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Araxes Pharma LLC; Liu, Yi; Li, Liansheng; Ren, Pingda; (176 pag.)US2018/15087; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 2436-29-5,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.

Into a heat-vacuum dried 50 mL recovery flask, DMF (13 mL), 3-phthalimidylpropanal (manufactured by Aurora Fine Chemicals, 266.0 mg, 1.13 mmol, 1 equivalent), N,N-diallylthioacetamide (244 muL, 1.35 mmol, 1.2 equivalents), and the Cu/(S,S)-Ph-BPE solution prepared as above (100 muL, 0.10 mmol, 0.09 equivalent) were added under an argon atmosphere. The recovery flask was transferred to a constant temperature bath of -40C, and the THF solution of 2,2,5,7,8-pentamethylchromanol lithium salt prepared as above (50 muL, 0.10 mmol, 0.09 equivalent) was added, followed by stirring at -40C for 24 hours. Subsequently, a saturated aqueous solution of ammonium chloride (5 mL) and 2,2-bipyridine (15.6 mg, 0.10 mmol, 0.09 equivalent) were added, and the resulting mixture was extracted three times with ethyl acetate (5 mL). The resulting organic layer was sequentially washed with distilled water, saturated sodium bicarbonate water, and saturated brine, and then dried over anhydrous sodium sulphate. After filtration and concentration, the residue thus obtained was purified by flash column chromatography (hexane/ethyl acetate = 7/1 to 2/1 (volume ratio)) to obtain the following thioamide compound A-4 as a yellow oily matter. Yield 251.1 mg (62%, 75%ee).

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

Reference:
Patent; Microbial Chemistry Research Foundation; SHIBASAKI, Masakatsu; KUMAGAI, Naoya; EP2679580; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 5394-18-3, name is 2-(4-Bromobutyl)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 5394-18-3, Computed Properties of C12H12BrNO2

General procedure: To a mixture of the corresponding R1R2NH (3.0 mmol), anhydrous K2CO3 (449 mg, 3.25 mmol) and KI (20.75 mg, 0.125 mmol) in CH3CN (12 ml) were added the appropriate intermediates 6-9 (2.5mmol). The reaction mixture was warmed to 60-65 C and stirred for 6-8 h under an argon atmosphere. After complete reaction, the solvent was evaporated under reduced pressure. Then water (25 mL) was added to the residue and the mixture was extracted with dichloromethane (25 mL×3). The combined organic phases were washed with saturated aqueous sodium chloride (30 mL), dried over sodium sulfate, and filtered. The solvent was evaporated to dryness under reduced pressure. The residue was purified on a silica gel chromatography using mixtures of petroleum ether/EtOAc as eluent, obtaining the corresponding intermediates 10-13a-d.

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; Li, Yuxing; Qiang, Xiaoming; Li, Yan; Yang, Xia; Luo, Li; Xiao, Ganyuan; Cao, Zhongcheng; Tan, Zhenghuai; Deng, Yong; Bioorganic and Medicinal Chemistry Letters; vol. 26; 8; (2016); p. 2035 – 2039;,
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. 446292-08-6, name is (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Recommanded Product: 446292-08-6

Add 4 kg of N-methylpyrrolidone to a 10 L reaction flask.Add 1.0kg of compound (II), add 0.3kg of 80% hydrazine hydrate, stir and heat.The reaction was stirred at 90 C for 4 h. The reaction solution was cooled to 45 ± 5 C,Add about 0.7kg of sulfuric acid, add the reaction, and cool the reaction solution to 5±5C for 1h~1.5h.Filtration, filter cake washed with N-methylpyrrolidone, ethanol,Transfer the wet product to the blast oven,The internal temperature of the oven was controlled to dry at 50-55 C for 16 ± 1 hour to obtain a white solid.Yield: 92%, product purity (HPLC): 99.5%.

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; Changzhou Pharmaceutical Factory Co., Ltd.; Guo Yijie; Jin Xiaofeng; Shao Zhichun; (13 pag.)CN110156768; (2019); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 2058-72-2, 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 2058-72-2 as follows.

General procedure: Isatin (10 mmol), 2,2,2-trifluoroethylamine hydrochloride (15 mmol) and p-toluenesulfonic acid (0.5mmol) were suspended in toluene (10 mL) in a two-neck flask with a water separator and a condenser.The mixture was then heated to separate the water until complete disappearance of the starting materials.After cooling to room temperature, the mixture was washed with a small quantity of saturated NaHCO3solution and dried by Na2SO4, After evaporation of the organic solvent, the crude residue was purified byflash chromatography (silica gel, hexane/EtOAc) and afforded the resulting ketimine.

According to the analysis of related databases, 2058-72-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Huang, Wei-Jie; Chen, Qing; Zhu, Wen-Run; Lin, Ning; Long, Xian-Wen; Pan, Wei-Gao; Weng, Jiang; Lu, Gui; Heterocycles; vol. 94; 5; (2017); p. 879 – 893;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 2058-72-2, 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. 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: At the first, a mixture containing (10% mol) aimin base ligand and transition metal salts (10% mol) was prepared in 10 ml dichloromethan. Then a mixture of isatin derivatives (1 mmol) and (S)-proline (1.1 mmol), in 10 mL ethanol was added to mixture. After completion of the reaction (monitored by TLC), the reaction mixture was extracted with dichloromethane (15 mL). The combined organic layer dried over anhydrous MgSO4. The organic layer was concentrated in vacuum to furnish the products, which were recrystallized from ethanol.

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; Taghizadeh, Mohammad Javad; Javidan, Abdollah; Jadidi, Khosrow; Journal of the Korean Chemical Society; vol. 59; 3; (2015); p. 205 – 208;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 1074-82-4, 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. 1074-82-4, name is Potassium 1,3-dioxoisoindolin-2-ide, This compound has unique chemical properties. The synthetic route is as follows.

(Synthesis of Intermediate 1)96.2 g (1.04 mol) of chloroacetone was added to 300 ml of N-methylpyrrolidone (NMP), and the mixture was stirred at 15 to 20 C. 175 g (0.945 mol) of phthalimide potassium was added in portions to the solution, while the temperature of reaction solution was kept at 30 C. or lower. After addition, the mixture was stirred at room temperature for two hours, to complete the reaction. After reaction, the reaction solution was poured into 3,000 ml of water, allowing precipitation of the crystal. The crystal was filtered, washed with water and dried, to give 163 g of an intermediate 1 (yield: 84.9%).

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

Reference:
Patent; FUJIFILM CORPORATION; US2012/238752; (2012); A1;,
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. Formula: C8H7NO

5-Acetyl-2-oxindole 2-Oxindole (3 g) was suspended in 1,2-dichloroethane and 3.2 mL acetyl chloride were slowly added. The resulting suspension was heated to 50 C. for 5 hours, cooled, and poured into water. The resulting precipitate was collected by vacuum filtration, washed copiously with water and dried under vacuum to give 2.9 g (73% yield) of the title compound as a brown solid.

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

Reference:
Patent; SUGEN, Inc.; US2003/69421; (2003); A1;; ; Patent; Sugen, Inc.; US6051593; (2000); A;,
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. 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Computed Properties of C9H6BrNO2

General procedure: The vacuum dried intermediate 3 (0.002 mol) was then reacted with mono- and di-substituted benzoic acids (0.003 mol) separately in presence of anhydrous potassium carbonate (0.003 mol) in DMF (10 mL). The reaction mixture was stirred at room temperature for about 2 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was poured into ice-cold water and allowed stir for 10 min. The solid obtained was filtered and washed successively with distilled water and recrystallized from ethanol to obtain4(a-n).

The synthetic route of 5332-26-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kumar, C.S. Chidan; Loh, Wan-Sin; Chandraju, Siddegowda; Win, Yip-Foo; Tan, Weng Kang; Quah, Ching Kheng; Fun, Hoong-Kun; PLoS ONE; vol. 10; 3; (2015);,
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Indoline | C8H9N – PubChem

These common heterocyclic compound, 552330-86-6, name is 5-Bromoisoindolin-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. Formula: C8H6BrNO

5-Bromoisoindolin-l-one (15 g, 70.74 mmol) and sodium methyl mercaptide (12.40 g,176.85 mmol) were mixed together in DMF (150 mL) and heated to 100 C for lh. The reaction mixture was cooled to room temperature and poured into water (160 mL), and the aqueous phase was extracted with EtOAc (400 mL). The layers were then separated and the aqueous phase extracted with EtOAc (3 x 200 mL). The combined organic extracts were washed with brine (3 x 100 mL), dried using a phase separator cartridge and concentrated in vacuo. 5-(Methylthio)isoindolin-1-one (12.00 g, 95%) was obtained as a yellow solid. The material was used in the next step without further purification. LC/MS: m/zrrl8O [M+H]. ?H NMR (500 MHz, DMSO-d6) i5 2.54 (s, 3H), 4.33 (s, 2H), 7.33 (d, 1H), 7.44 (s, 1H), 7.56 (d, 1H), 8.43 (s, 1H).

The synthetic route of 5-Bromoisoindolin-1-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; LEVER, Sarah; NARJES, Frank; OLSSON, Roine, Ingemar; VON BERG, Stefan; (124 pag.)WO2018/229155; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem