Month: February 2021

Electric Literature of 16800-68-3, A common heterocyclic compound, 16800-68-3, name is 1-Acetylindolin-3-one, molecular formula is C10H9NO2, 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: 1a (35.0 mg, 0.2 mmol, 1 equiv.), tert-BuOK (22.4 mg, 0.2 mmol, 1.0 equiv.) were added to a Schlenk tube. Then 2 ml THF was added using a syringe. The reaction mixture was stirred 15min,and then added iodonium salt 2 (0.2 mmol, 1.0 eq). The reaction was stirred at 30C for 10 hours.After cooling to room temperature, the solvent was removed in vacuo and the residue was purifiedby silica gel using a proper eluent (EtOAc/Hexane) to afford the desired products

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, Yanxia; Han, Jianwei; Liu, Zhen-Jiang; Synlett; vol. 26; 18; (2015); p. 2593 – 2597;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-one, 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: C10H9Cl2NO

2 moles of Piperazine Benzisothiazole , 1 mole of 5-(2-chloroethyl)-6- chlorooxindole in water (20 times based on benzisothiazole) and in the presence of dispersing agent. All the reactants are charged in to the flask and refluxed under nitrogen, -under stirring ^or^ r2-i6hr. After the completion “of the reaction,” the” reaction mass is cooled to room temperature and the resulting mass is filtered. It is slurried inwater and then in IPA and isolated by filtration. The solid is dried at 95- 1000C.Yield: 92%, Purity 99 %( min).

The synthetic route of 118289-55-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALKEM LABORATORIES LTD.; WO2009/116085; (2009); A2;,
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 64483-69-8 as follows. category: indolines-derivatives

General procedure: Indolinone 1 (1000 mg, 52.3 mmol) was suspended in acetic anhydride (10 mL) and refluxed at 130 C for 8 h. The reaction mixture was allowed to cool to 50 C and (triethoxymethyl)benzene(2930 mg, 131 mmol) was added. The resulting reaction mixture was stirred at 120 C for 6 h. Then, volatiles were removed in vacuo and petroleum ether was added to the obtained residue. After triturating for 15 min, the separated solids were filtered and washed with petroleum ether and then dried under vacuum to afford974 mg (51%) of title compound.

According to the analysis of related databases, 64483-69-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Edupuganti, Ramakrishna; Taliaferro, Juliana M.; Wang, Qiantao; Xie, Xuemei; Cho, Eun Jeong; Vidhu, Fnu; Ren, Pengyu; Anslyn, Eric V.; Bartholomeusz, Chandra; Dalby, Kevin N.; Bioorganic and Medicinal Chemistry; vol. 25; 9; (2017); p. 2609 – 2616;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 102359-00-2, 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.

EXAMPLE 45 To a suspension of 1.76 g of 5-carboxyoxindol in 200 ml of methylene chloride was added 2 ml of pyridine. After completion of addition, to the suspension was added dropwise 1.4 g of thionyl chloride with stirring held at 0 to 20 C. After completion of addition, the mixture was stirred at the same temperature for 1 hour, and a solution of 1.74 g of benzylpiperazine in 10 ml of methylene chloride was added dropwise thereto. The mixture was then stirred for 4 hours at room temperature. The reaction mixture was thoroughly washed with an aqueous potassium carbonate solution, then washed with water, and dilute hydrochloric acid, dried over sodium sulfate, and the solvent was distilled off. The residue was isolated and purified by silica-gel column chromatography [silica-gel: WAKO C-200, eluent: chloroform:methanol (V/V)=20:1] followed by recrystallization from isopropyl alcohol to give 298 mg of 5-(4-benzyl-1-piperazinylcarbonyl)oxindol. m.p.: 151-153 C.

The synthetic route of 102359-00-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Otsuka Pharmaceutical Co., Ltd.; US4737501; (1988); A;,
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. 3783-77-5, name is 2-(3-Oxobutyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C12H11NO3

To a solution of spiro[isobenzofuran-1(3H), 4′-piperidine] hydrochloride (2.80 g) and 2-(3-oxobutyl)-1H-isoindol-1,3(2H)-dione (2.0 g) in THF-methanol (1:1 v/v, 40 ml), 0.3 M sodium cyanoborohydride-1/2 zinc chloride solution in methanol (44 ml) was added and stirred for 20 hours at room temperature. Saturated aqueous sodium hydrogencarbonate solution was added to the reaction liquid, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and condensed under reduced pressure. The resulting solid was washed with a small amount of methanol to provide 2-(3-spiro[isobenzofuran-1(3H), 4′-piperidin-1-yl]butyl-1H-isoindol-1, 3(2H)-dione (578 mg) as a white solid.

According to the analysis of related databases, 3783-77-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BANYU PHARMACEUTICAL CO., LTD.; EP1595867; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 954-81-4, name is N-(5-Bromopentyl)phthalimide, 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 954-81-4, Recommanded Product: N-(5-Bromopentyl)phthalimide

Under a protective nitrogen atmosphere, sodium hydride (NaH, 48 mg, 1.2 mmol) is added into a solution of berbamine dihydrochloride (205 mg, 0.3 mmol) in N,N-dimethyl formamide (5 ml) at 0 C., after being stirred for 1 hour, 2-(5-bromoamyl)-isoindoline-1,3-dione (133 mg, 0.45 mmol) is added therein. The reaction solution is heated to 80 C. overnight. Then the reaction mixture is evaporated under vacuum, and purified by a preparative thin layer chromatography to give white or pale yellow compound (BS-BE-002) (98.4 mg, 39.8%). [0109] LC/MS m/z: M+1 824.2 100% (purity). 1H NMR (CDCl3) delta:7.8267.809 (dd, 2H, J=5.5 Hz, 5.5 Hz), 7.6927.680 (dd, 2H, J=6.0 Hz, 5.5 Hz), 7.267.243 (m, 2H), 7.0847.071 (d, 1H, J=6.5 Hz), 6.796.733 (m, 2H), 6.6236.607 (d, 1H, J=8.0 Hz), 6.529 (s, 1H), 6.395 (s, 1H), 6.272 (s, 1H), 5.971 (s, 1H), 4.0694.042 (t, 2H, J=6.5 Hz, 7.0 Hz), 3.783 (s, 2H), 3.750 (s, 3H), 3.7183.689 (t, 2H, J=7.0 Hz, 7.5 Hz), 3.610 (s, 1H), 3.399 (s, 1H), 3.2453.208 (m, 2H), 3.121 (s, 3H), 3.0232.779 (m, 6H), 2.569 (s, 3 H), 2.540 (s, 1H), 2.3702.338 (m, 1H), 2.250 (s, 3H), 1.9261.869 (m, 2H), 1.7884.682 (m, 3H), 1.5701.507 (m, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, N-(5-Bromopentyl)phthalimide, and friends who are interested can also refer to it.

Reference:
Patent; HANGZHOU BENSHENG PHARMACEUTICAL CO., LTD.; Xu, Rongzhen; Rong, Frank; Xie, Fuwen; Lai, Hongxi; US2013/158068; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 16800-68-3, name is 1-Acetylindolin-3-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. Application In Synthesis of 1-Acetylindolin-3-one

General procedure: To 5-bromo-N-acetyl indoxyl (0.018 mole), Titanium isopropoxide (0.027 mole) was added under nitrogen atmosphere. The mass was stirred for 30 min at room temperature. N-Methyl piperazine (0.02 mole) was added neat to the above complex. The reaction mass was further at room temperature for 5 hr. Absolute ethanol (20 mL) was added to the thick slurry mass followed by the addition of sodium triacetoxyborohydride (0.036 mole). After completion of the reaction (TLC), the reaction mass was diluted with water (100 mL) and the precipitated titanium complex was removed by filtration. The solid on the filter was washed with ethyl acetate till colourless filtrate was obtained. The filtrate was basified with aqueous ammonia whereby compound went into organic layer. The organic layer was separated, washed with brine solution (1 x 50 mL) and dried over anhydrous magnesium sulfate. Solvent was removed under reduced pressure and the residual mass was purified by flash chromatography over silica gel using 70 % ethylacetate in n-hexane to obtain the title compound in 70% yield.

The synthetic route of 1-Acetylindolin-3-one has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nirogi, Ramakrishna V.S.; Deshpande, Amol D.; Kambhampati, Ramasastri; Badange, Rajesh Kumar; Kota, Laxman; Daulatabad, Anand V.; Shinde, Anil K.; Ahmad, Ishtiyaque; Kandikere, Vishwottam; Jayarajan, Pradeep; Dubey; Bioorganic and Medicinal Chemistry Letters; vol. 21; 1; (2011); p. 346 – 349;,
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, Recommanded Product: 6-Chloroisatin

D. 6-Chloro-2-oxindole Reaction of 36.2 g of 6-chloroisatin with hydrazine hydrate followed by sodium ethoxide in ethanol, substantially according to C above, afforded 14.2 g of 6-chloro-2-oxindole, mp 196-198 C.

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; Pfizer Inc.; US4658037; (1987); A;; ; Patent; Pfizer Inc.; US4652658; (1987); A;,
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. 19727-83-4, name is 6-Nitroindoline, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C8H8N2O2

To a solution of 6-nitroindoline (13) (590 mg, 3.6 mmol), tert-butyl 4-oxopiperidine-1-carboxylate (860 mg, 4.3 mmol) in acetic acid (10.0 mL) was added sodium triacetoxyborohydride (1.14 g, 5.4 mmol) at 0C and the reaction mixture was stirred for 1 hr at this temperature and then heated to room temperature overnight. After the reaction completed, water was added to the the mixture and the mixture was extracted with CH2Cl2. The organic phase was washed with water and saturated NaHCO3, dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated under reduced pressure to afford the crude product, which was purified by column chromatography to give the tert-butyl 4-(6-nitroindolin-1-yl) piperidine-1-carboxylate (14) 0.92 g, yield: 73.6%. 1H NMR (400 MHz, DMSO-d6) delta 8.77 (s, 1H), 7.89 (d, J = 8.1 Hz, 1H), 7.47 (d, J = 8.1 Hz, 1H), 4.20 (t, J = 8.5 Hz, 2H), 3.29(m, 4H), 3.26 (t, J = 8.5 Hz, 2H), 2.93(m, 1H), 2.20(m, 3H), 1.67(m, 1H), 1.38(m, 9H). MS (ESI) m/z: 348 [M+H]+.

According to the analysis of related databases, 19727-83-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Tian, Jinlong; Sun, Nannan; Yu, Mingcheng; Gu, Xianfeng; Xie, Qiong; Shao, Liming; Liu, Jin; Liu, Li; Wang, Yonghui; European Journal of Medicinal Chemistry; vol. 167; (2019); p. 37 – 48;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 86626-38-2,Some common heterocyclic compound, 86626-38-2, name is 4-Bromoindoline, molecular formula is C8H8BrN, 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.

A mixture of above obtained 4-bromoindoline (759 mg, 3.81 mmol), and (Boc)2O (976 mg, 4.48 mmol) in MeCN (8 mL) was stirred at room temperature overnight. After evaporated, the residue was dissolved in ethyl acetate (40 mL), washed with water (3¡Á20 mL) and brine (1¡Á20 mL). The organic layer was concentrated and purified by column chromatography on silica gel (petroleum ether) to give 0601-177 (840 mg, 74%) as a white solid. 1H-NMR (400 MHz. DMSO-d6) delta 1.50 (s, 9H), 3.02 (t, J=8.8 Hz, 2H), 3.94 (t, J=8.8 Hz, 2H), 7.12 (m, 2H), 7.56 (m, 1H).

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

Reference:
Patent; Curis, Inc.; Bao, Rudi; Lai, Chengjung; Qian, Changgeng; US2013/102595; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem