Month: August 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. 24566-79-8, name is N-(6-Bromohexyl)phthalimide, A new synthetic method of this compound is introduced below., name: N-(6-Bromohexyl)phthalimide

General procedure: A mixture of the intermediates 3a-3e (5 mmol) and corresponding secondary amine 4a-4g (5.5 mmol) was added in CH3CN (20 ml) at the presence of anhydrous K2CO3 (6 mmol). The mixture was heated at 65 C for 6-10 h. The solvent was evaporated in vacuo. The residue was dissolved in CH2Cl2 (25 mL), washed with water (20 mL × 3), and the combined organic phases were washed with saturated aqueous NaCl (30 mL), dried over sodium sulfate, and filtered. The solvent was evaporated under reduced pressure. The residue was purified on a silica gel chromatography using mixtures of petroleum/acetone as eluent to get the target products TM-1~TM-28.

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:
Article; Sang, Zhipei; Wang, Keren; Wang, Huifang; Yu, Lintao; Wang, Huijuan; Ma, Qianwen; Ye, Mengyao; Han, Xue; Liu, Wenmin; Bioorganic and Medicinal Chemistry Letters; vol. 27; 22; (2017); p. 5053 – 5059;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 32692-19-6, A common heterocyclic compound, 32692-19-6, name is 5-Nitroindoline, molecular formula is C8H8N2O2, 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: 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.

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:
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

Adding a certain compound to certain chemical reactions, such as: 959235-95-1, name is 6-(Trifluoromethoxy)indoline, 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 959235-95-1, Quality Control of 6-(Trifluoromethoxy)indoline

Under N2 flow at 5C, propylphosphonic anhydride (2.56 ml_, 4.26 mmol) was added dropwise to a mixture of 6-(thfluoromethoxy)indoline [CAS 953906-76-8] (577 mg, 2.84 mmol), 2-(4-chlorophenyl)-2-((3-(2-hydroxyethoxy)-5-methoxy- phenyl)amino)acetic acid 3f (1 .3 g, 3.70 mmol) and diisopropylethylamine (1 .03 ml_, 6.25 mmol) in 2-Me-THF (30 ml_). The mixture was stirred at room temperature for 4 h. Water was added and the mixture was extracted with EtOAc. The organic layer was washed with a 10% solution of K2CO3 in water and then with water, dried over MgSO4, filtered, and the solvent was evaporated under reduced pressure. Purification was carried out by flash chromatography on silica gel, (15-40 muiotatauiota, 40 g, Ch C /MeOH 99/1 ). The pure fractions were combined and evaporated to dryness, to give 2-(4-chlorophenyl)-2-((3-(2-hydroxyethoxy)-5- methoxyphenyl)amino)-1 -(6-(trifluoromethoxy)indolin-1 -yl)ethanone (Compound 3, 800 mg) as a racemic mixture. This fraction was combined with another batch (total amount: 1 .4 g) and crystallized from diisopropyl ether to give 1 .03 g of Compound 3. The enantiomers were separated via Preparative Chiral SFC (Stationary phase: Chiralpak IA 5 muetaeta 250 x 20 mm, Mobile phase: 55% CO2, 45% EtOH (+ 0.3% iPrNh )). The first eluted enantiomer was further purified via reverse phase chromatography (stationary phase: X-bridge-C-18 10 m 30 x 150 mm, mobile phase: 0.2% NH4HCO3/CH3CN gradient 60/40 to 0/100) to give Enantiomer 3A (312 mg). The second eluted Enantiomer 3B (436 mg) was not further purified.

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-(Trifluoromethoxy)indoline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JANSSEN PHARMACEUTICALS, INC.; KATHOLIEKE UNIVERSITEIT LEUVEN; BARDIOT, Dorothee Alice Marie-Eve; BONFANTI, Jean-Francois; KESTELEYN, Bart Rudolf Romanie; MARCHAND, Arnaud Didier M; RABOISSON, Pierre Jean-Marie Bernard; (76 pag.)WO2017/167953; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 13220-46-7,Some common heterocyclic compound, 13220-46-7, name is 4-Methylindolin-2-one, molecular formula is C9H9NO, 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.

Example 3 3-(3H-Isobenzofuran-1-ylidene)-4-methyl-1,3-dihydro-indol-2-one To a solution containing 4-methyloxindole (0.15 g, 1.02 mmol) and phthalide (0.178 g, 1.33 mmol) in 3.0 mL DMF was added 2.14 mL of sodium hexamethyldisilazane (1.0 M in tetrahydrofuran (THF)) over 1 min. The solution was stirred at room temperature for 30 min and then poured into 50 mL of 4% HCl to give a yellow solid. The aqueous mixture was extracted with EtOAc and the organic phase washed with saturated NaHCO3, H2O, dilute HCl, brine and the solution dried with Na2SO4. The solvent was removed in vacuo and the solid obtained was purified by chromatography (silica gel, CHCl3/EtOAc, 7:3). The solid obtained was recrystallized from EtOAc/hexanes to afford the title compounds (3.8 mg) as a yellow solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Methylindolin-2-one, its application will become more common.

Reference:
Patent; Allergan Sales, LLC; US6541504; (2003); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 6872-06-6,Some common heterocyclic compound, 6872-06-6, name is 2-Methylindoline, molecular formula is C9H11N, 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 compound 65 (0.20g, 0.77mmol) in anhydrous DMF (1mL) was added HATU (0.29g, 0.77mmol), the mixture was stirred at rt for 30min, then DIPEA (0.13mL, 0.77mmol) and p-toluidine (0.083g, 0.77mmol) was added. The mixture was stirred at rt for another 12h and monitored by TLC. Upon completion, the reaction mixture was diluted with water and extracted with EtOAc (3*20mL). The combined organic fractions were washed with brine, dried over Na2SO4, concentrated by evaporation under reduced pressure. Purification by silica gel column chromatography (gradient elution, gradient 0-25% EtOAc/60-90C petroleum ether) gave compound 7 (0.15g, 0.43mmol, 56% yield) as a white solid.

The synthetic route of 6872-06-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Hu, Jianping; Wang, Yingqing; Li, Yanlian; Cao, Danyan; Xu, Lin; Song, ShanShan; Damaneh, Mohammadali Soleimani; Li, Jian; Chen, Yuelei; Wang, Xin; Chen, Lin; Shen, Jingkang; Miao, Zehong; Xiong, Bing; European Journal of Medicinal Chemistry; vol. 150; (2018); p. 156 – 175;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 6341-92-0, name is 6-Chloroisatin, 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 6341-92-0, Computed Properties of C8H4ClNO2

General procedure: A mixture of the isatin 1 or acenaphthenequinone 4 (1 mmol), indole 2 (2 mmol), p-TSA (10mol %), CH2Cl2 (10 mL) was added to 50 mL flask and stirred at room temperature until the thecompletion of the reaction (Scheme 1, 2). Then the solid was filtered and washed with CH2Cl2 (5mL) and ethanol (5 mL) in turns, affording the product in excellent yields, which wasrecrystallized from ethanol to produce pure crystalline products. The products were identified byelemental analysis, MS, 1H NMR, 13C NMR, and IR spectra.

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

Reference:
Article; Yu, Jiangxia; Shen, Tianhua; Lin, Yan; Zhou, Yongbing; Song, Qingbao; Synthetic Communications; vol. 44; 14; (2014); p. 2029 – 2036;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 2913-97-5, name is N-(2-Oxoethyl)phthalimide, molecular formula is C10H7NO3, 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: 2913-97-5

Aldehyde reaction partner selection was key in order to assign donor and acceptor roles to aldehydes in the previously discussed aldol reaction. Aldol reactions between Compound 1 and oc-non-branched aldehydes such as isovaleraldehyde and hexanal afforded P-hydroxy-y- (diprotected) amino aldehydes Compounds 6 under identical conditions to those used in Table 5 (see, Scheme 10, hereinbelow, wherein R is a non-branched substituent containing at least two hydrogen atoms) . No formation of (3-hydroxy-a-amino aldehydes was detected. In these instances, aldehyde Compound 1 acted as the acceptor. Slow addition of aldehyde Compound 1 to isovaleraldehyde in thepresence of the catalyst did not change the outcome of the reaction.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2913-97-5, its application will become more common.

Reference:
Patent; THE SCRIPPS RESEARCH INSTITUTE; WO2006/23720; (2006); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 480-91-1, These common heterocyclic compound, 480-91-1, name is Isoindolin-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.

General procedure: Isoindolin-1-one (200 mg, 1.50mmol) was dissolved in super-dry DMSO (4 mL), and Cs2CO3 (1215 mg, 3.75 mmol), CuI (58 mg, 0.30mmol) and N1,N2-dimethylethane-1,2-diamine (27 mg, 33 muL, 0.30 mmol) were added to the solution.The resulting mixture was stirred at room temperature for 10 min, after which iodobenzene (2.25mmol) was added. Then the mixture was heated to 120 C. When TLC showed that isoindolin-1-onehad been fully converted, the reaction was stopped. The mixture was extracted with ethyl acetate (20mL) and H2O (10 mL). The water phase was re-extracted with ethyl acetate (20 mL). The organic layerwas combined and washed with brine (10 mL). Then the solution was dried over anhydrous MgSO4,filtered and concentrated, and the crude residue was purified by flash chromatography over silica gelusing CH2Cl2/CH3OH as the gradient elution to afford the title compounds.

The synthetic route of 480-91-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Yixuan; Wang, Huiqiang; Jiang, Xinbei; Jiang, Zhi; Guo, Tingting; Ji, Xingyue; Li, Yanping; Li, Yuhuan; Li, Zhuorong; Molecules; vol. 24; 5; (2019);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 19727-83-4, 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. 19727-83-4, name is 6-Nitroindoline, This compound has unique chemical properties. The synthetic route is as follows.

To a mixture of 6-nitroindoline (2 mmol) and TEA (2.2 mmol) in CH2Cl2 (20 mL) was added di-tert-butyl dicarbonate (2 mmol). The mixture was stirred at 25 C. for 16 h. The mixture was washed with satd. aq. NaHCO3 (20 mL) and brine (20 mL), and then was dried and concentrated.

The chemical industry reduces the impact on the environment during synthesis 6-Nitroindoline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Carruthers, Nicholas I.; Chai, Wenying; Dax, Scott L.; Jablonowski, Jill A.; Li, Xiaobing; Lovenberg, Timothy W.; Murray, William V.; Rudolph, Dale A.; Seierstad, Mark; Youngman, Mark A.; US2005/70534; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products 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.

Step B : 5-methoxy-1-nitroso-2,3-dihydro-1H-indole; To 10 ml of 50% acetic acid solution at 0 C. there is added, all at once, 0.499 g of the compound of Step A above. At 0 C., 0.232 g of sodium nitrite dissolved in 5 ml of water is added dropwise. Once the addition is complete, the reaction mixture is stirred at 0 C. for 1 hour 30 minutes. After adding water, the aqueous phase is extracted 3 times with dichloromethane; the combined organic phases are washed with water and dried over magnesium sulphate. Evaporation to dryness yields the expected product, which is used in the subsequent reaction without purification.

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; LES LABORATOIRES SERVIER; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; UNIVERSITE PARIS SUD; US2009/176794; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem