Category: indolines-derivatives

Adding a certain compound to certain chemical reactions, such as: 104618-31-7, name is 2-(4-Hydroxycyclohexyl)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 104618-31-7, Recommanded Product: 104618-31-7

To a solution of PPh3 (1.28 g, 4.9 mmol) in THF (12 mL) was added dropwise DEAD (852 mg, 4.9 mmol) at -10 C. After the white solid was appeared, compound 2-(4-hydroxycyclohexyl)isoindoline-1,3-dione (600 mg, 2.45 mmol) was added, followed by CH3COSH (0.35 mL, 4.9 mmol) at -10 C. The mixture was stirred at room temperature overnight. TLC (PE:EA=1:1) showed the reaction was complete. The mixture was poured into water (200 mL) and extracted with EtOAc (100 mL). The aqueous layer was extracted with EtOAc (100 mL×3). The combined extracts were dried over Na2SO4, filtered and concentrated in vacuo to give S-(4-(1,3-dioxoisoindolin-2-yl)cyclohexyl) ethanethioate (600 mg, 81%) as a white solid.

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

Reference:
Patent; Tolero Pharmaceuticals, Inc.; Xu, Yong; Brenning, Benjamin Gary; Kultgen, Steven G.; Liu, Xiaohui; Saunders, Michael; Ho, Koc-Kan; (119 pag.)US9416132; (2016); B2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 104618-31-7, These common heterocyclic compound, 104618-31-7, name is 2-(4-Hydroxycyclohexyl)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.

To a mixture of 7-bromoquinoxalin-5-ol (47.53 g, 211.2 mmol), 2-(4- hydroxycyclohexyl)isoindoline-l,3-dione (52.41 g, 213.7 mmol), and PPh3 (87.31 g, 332.9 mmol) in THF (740 mL) at 21 C was added tert-butyl (NZ)-N-tert- butoxycarbonyliminocarbamate (DTBAD) (79.51 g, 328.0 mmol) in portions over 40 min so as to maintain the temperature below 30 C and the resultant reaction mixture was stirred at room temperature for a further 20 h. The reaction was evaporated in vacuo. The residual reddish-brown viscous oil was dissolved in CH2C12 and filtered through a plug of silica in a glass column using applied air pressure (plug was made with 1L of dry silica suspended in CH2C12). The plug was eluted with CH2C12, the fractions were combined and evaporated in vacuo to afford a red-brown viscous oil/foam, that was then dissolved in 700 mL of MeOH before precipitating. The mixture was stirred at room temperature for 1 h, filtered, washed with cold MeOH (500 mL) and Et20 (100 mL), then dried in vacuo to yield a tan solid that was suspended in 300 mL MeOH and brought to reflux for 10 min. The suspension was cooled to room temperature and filtered, washed with a further MeOH and Et20 (4: 1), and dried in vacuo to provide 2-[4-(7- bromoquinoxalin-5-yl)oxycyclohexyl]isoindoline-l,3-dione (58.43 g, 126.6 mmol, 59.94%). 1H NMR (400 MHz, CDC13) d 8.96 (d, J = 1.8 Hz, 1H), 8.86 (d, J = 1.8 Hz, 1H), 7.91 (d, J = 1.9 Hz, 1H), 7.89 – 7.82 (m, 2H), 7.78 – 7.67 (m, 2H), 7.30 (d, J = 1.9 Hz, 1H), 4.95 (s, 1H), 4.29 (tt, J = 12.5, 3.7 Hz, 1H), 2.87 (qd, J = 13.1, 3.5 Hz, 2H), 2.44 (d, J = 15.2 Hz, 2H), 1.80 (t, J = 14.1 Hz, 2H), 1.67 (d, 2H). ESI-MS m/z calc. 451.05316, found 452.19 (M+l)+; Retention time: 0.92 minutes.

Statistics shows that 2-(4-Hydroxycyclohexyl)isoindoline-1,3-dione is playing an increasingly important role. we look forward to future research findings about 104618-31-7.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WEINBERG, Marc, Saul; D’ASTOLFO, Diego, Sebastian; MAHAJAN, Sudipta; (258 pag.)WO2019/143675; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 5181-35-1, 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. 5181-35-1, name is 2-(2-Bromoethoxy)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 2-(2-bromoethoxy)isoindoline- l,3-dione (20 g, 74 mmol, prepared according to the procedure described in step 1 of preparation 38), (lH-tetrazol- 5-ylmethyl)-carbamic acid tert-butyX ester (7.66 g, 74 mmol, prepared as per procedure described in step 2 of preparation 19) in dimethylformamide (100 ml) was added cesium carbonate (24.13 g, 74 mmol) lot wise under stirring at 25 C. After 16 hours, the reaction mixture was filtered and filtrate was slowly poured into chilled water (700 ml) and stirred for 30 minutes. The precipitated compound was filtered and washed with water (100 ml). The solid compound was dried at 35C for 2 hours under high vacuum, to provide 16 g of tert-butyX [(2-{2-[(l,3-dioxo- l,3-dihydro-2H- isoindol-2-yl)oxy]ethyl}-2H-tetrazol-5-yl)methyl] carbamate in 55% yield. Analysis: Mass: 389.4 (M+l); for Molecular weight: 388 and Molecular formula: Ci7H20N6O5.

The chemical industry reduces the impact on the environment during synthesis 2-(2-Bromoethoxy)isoindoline-1,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Patent; WOCKHARDT LIMITED; TADIPARTHI, Ravikumar; PATIL, Vijaykumar Jagdishwar; DEKHANE, Deepak; SHAIKH, Mohammad Usman; BIRAJDAR, Satish; DOND, Bharat; PATEL, Mahesh Vithalbhai; (100 pag.)WO2017/81615; (2017); 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. 1127-59-9, name is 7-Methylindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows., category: indolines-derivatives

A solution of 7-methylindoline-2,3-dione (7.08 g, 44 mmol), NaOH (1.77 g, 44 mmol) and KCl (7.08 g, 95 mmol) in water (80ml) was cooled to 0 C and 33% H2O2 (6.02 mL, 0.66 mmol) was added dropwise over 1.5 hours. After an additional 45 minutes at room temperature the addition of acetic acid (16 mL) caused precipitation of the product. Recrystallization from water gave the title compound (5.26 g, 80%) as a pale brown solid. mp 162 – 164 C (Litt7. 174 – 176 C). 1H NMR (300 MHz, DMSO-d6) delta 7.61 (dd, J = 8.0, 1.3 Hz, 1H), 7.13 (dd, J = 7.1, 1.3 Hz, 1H), 6.45 (dd, J = 8.0, 7.1 Hz, 1H), 2.10 (s, 3H). 13C NMR (75 MHz, DMSO-d6) delta 169.9, 149.6, 134.3, 129.0, 122.9, 114.3, 109.3, 17.7

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 1127-59-9.

Reference:
Article; Hansen, Martin; Jacobsen, Stine Engesgaard; Plunkett, Shane; Liebscher, Gudrun Eckhard; McCorvy, John D.; Braeuner-Osborne, Hans; Kristensen, Jesper Langgaard; Bioorganic and Medicinal Chemistry; vol. 23; 14; (2015); p. 3933 – 3937;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 6941-75-9, name is 5-Bromoisoindoline-1,3-dione, molecular formula is C8H4BrNO2, 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. category: indolines-derivatives

To a solution of 4-bromophthalimide (22.6 g, 100 mmol) in dried tetrahydrofuran (250 mL) was added dropwise borane-dimethyl sulfide complex (51 mL, 500 mmol), stirred at room temperature for 2 hours, and then refluxed overnight. After cooling, methanol was carefully added dropwise to quench the excess borane. The resulting mixture was evaporated and concentrated, and then the residue was purified by silica gel column chromatography to give 5-bromoisoindoline (10.36 g). Yield: 52%. MS m/z[ESI]: 198.0[M+1].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6941-75-9, its application will become more common.

Reference:
Patent; Centaurus BioPharma Co., Ltd.; Chai Tai Tianqing Pharmaceutical Group Co., Ltd.; Lianyungang Runzhong Pharmaceutical Co., Ltd.; XU, Xinhe; SHEN, Yu; XIAO, Dengming; LUO, Hong; PENG, Yong; HAN, Yongxin; ZHANG, Aiming; YANG, Ling; (51 pag.)EP3257857; (2017); A1;,
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. 3484-35-3, name is 5-Methylindolin-2-one, A new synthetic method of this compound is introduced below., SDS of cas: 3484-35-3

General procedure: To a solution of 3-substituted-5-benzylidene-2-thioxo-4-thiazolidinone (3a-3h, 8a-8f) (0.003 mol) in 1,4-dioxane (15 ml) was added HC(OEt)3 (2 ml) and BF3·Et2O (2 ml). The reaction mixture was heated to 80 C and stirring was continued at the same temperature for 4 h. The resulting 2-ethylthio-3-substituted-5-benzylidene-4-thiazolium fluoroborate (4a-4h, 9a-9f) was precipitated, filtered off, and dried without any additional purification, as starting material for the following reactions. To a mixture of thiazolium fluoroborate (4a-4h, 9a-9f) (0.003 mol) and indolin-2-one (11a-11f) (0.003 mol) in acetonitrile (15 ml) was added triethylamine (0.91 g, 0.009 mol) dropwise at 25 C, and the mixture was stirred for 4 h at the same temperature. The orange precipitate was collected and washed with ethyl acetate (8 ml). The crude product thus obtained was recrystallized from methanol or acetone to give compound (5a-5s, 10a-10s).

The synthetic route of 3484-35-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Shuobing; Zhao, Yanfang; Zhang, Guogang; Lv, Yingxiang; Zhang, Ning; Gong, Ping; European Journal of Medicinal Chemistry; vol. 46; 8; (2011); p. 3509 – 3518;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 15937-07-2, name is 5,6-Dimethoxyindoline, 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 15937-07-2, Product Details of 15937-07-2

The experimental steps and operations are: at room temperature,18 g of Compound 2 was dissolved in 200 mL of acetonitrile, and the mixture was vigorously stirred in an environment where the container was exposed to air or oxygen, and the reaction was continued.The TLC tracks the reaction until the material completely disappears, which takes approximately 16-24 hours.The crude product was concentrated under reduced pressure on a rotary evaporator, and purified using silica gel column chromatography eluting with petroleum ether ethyl acetate (90:10, v/v).Obtaining Compound 3 as a colorless crystal; placing a single crystal in the receiving bottle. The weight of the compound 3 was 11.5 g, and the yield was 71% (the total yield of the two-step reaction).

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, 5,6-Dimethoxyindoline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Yantai Liudi Pharmaceutical Technology Co., Ltd.; Yang Jiade; Wang Xiujie; Fan Yulong; Qu Wenchao; Chen Tingting; (14 pag.)CN108484471; (2018); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 56341-37-8, name is 6-Chlorooxindole, 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 6-Chlorooxindole

General procedure: To the 3-subtitutedphenyl-1H-pyrazole-5-carbaldehydes 11(a-d) prepared in the above step was added corresponding substituted oxindoles and catalytic amount of piperdine (1.0ml) in ethanol. Heated the reaction mixture to reflux for 4h at 85C. The solid compounds obtained in the reaction vessel were filtered and washed with ethanol for 4-5 times. After complete air drying the final compounds (Z)-3-((3-phenyl-1H-pyrazol-5-yl)methylene)indolin-2-one analogs 12(a-u) were obtained as pure solids (yield 75-80%).

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

Reference:
Article; Kamal, Ahmed; Shaik, Anver Basha; Jain, Nishant; Kishor, Chandan; Nagabhushana, Ananthamurthy; Supriya, Bhukya; Bharath Kumar; Chourasiya, Sumit S.; Suresh, Yerramsetty; Mishra, Rakesh K.; Addlagatta, Anthony; European Journal of Medicinal Chemistry; vol. 92; (2015); p. 501 – 513;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 6341-92-0, A common heterocyclic compound, 6341-92-0, name is 6-Chloroisatin, molecular formula is C8H4ClNO2, 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 117 2-(6-Chloro-2,3-dioxo-2,3-dihydro-indol-1-yl)-3-cyclopentyl-N-thiazol-2-yl-propionamide A mixture of sodium hydride (60% in oil, 264 mg) in N,N-dimethylformamide at 0 C. was treated with a solution of 6-chloro-1H-indole-2,3-dione (1.0 g) in N,N-dimethyl formamide (total volume is 25 mL). The reaction mixture was then stirred for 30 min at 0 C. After this time, the reaction mixture was treated with 2-bromo-3-cyclopentyl-propionic acid methyl ester (prepared as in Example 1, 1.55 g) and stirred for another 1 h at 0 C. The reaction mixture was then allowed to warm to room temperature and stirred for 3 h. After this time, the reaction was diluted with water and extracted with methylene chloride. The organic layers were combined and then dried over sodium sulfate, filtered to remove the drying agent and the filterate concentrated in vacuo. The residue obtained was then purified by silica gel column chromatography to afford 2-(6-chloro-2,3-dioxo-2,3-dihydro-indol-1-yl)-3-cyclopentyl-propionic acid methyl ester (1.4 g, 76%).

The synthetic route of 6341-92-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kester, Robert Francis; US2012/142705; (2012); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 954-81-4, 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. 954-81-4, name is N-(5-Bromopentyl)phthalimide belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Procedure M1. A mixture of the appropriate 2-(bromoalkyl)isoindoline-1,3-dione (1 equiv) with amine (pyrrolidine or morpholine) (1.1 equiv) in the presence of K2CO3 (3 equiv) was stirred in acetonitrile under reflux for 20 h. Subsequently, the solvent was evaporated under reduced pressure,producing a residue which was further dissolved in 20 mL of water and extracted with DCM(3 x 30 mL). The organic layer was dried with anhydrous Na2SO4. The solvent was then evaporated and the residue was purified by silica gel column chromatography (S3) yielding a yellow oil. The finalproduct was transformed into hydrochloride salt. The following compounds were obtained. 2-(5-(Pyrrolidin-1-yl)pentyl)isoindoline-1,3-dione (1) [55]. Procedure M1. Reaction of 2-(5-bromopentyl)isoindoline-1,3-dione [37] (0.5 g, 1.69 mmol) with pyrrolidine (0.13 g, 1.86 mmol) and K2CO3 (0.7 g,5.1 mmol) in acetonitrile (25 mL), after 20 h, column chromatography gave oil product. Yield 0.35 g(73%). TLC (S3) Rf = 0.13. MW 286.17. Formula: C17H22N2O2. MS: m/z 287.28 [M + H]+. 1H-NMR(300 MHz, CDCl3) delta ppm: 7.89-7.77 (m, 2H), 7.78-7.65 (m, 2H), 3.69 (t, J = 6.9 Hz, 2H), 3.00 (m, 4H),2.06-1.88 (m, 4H), 1.81-1.65 (m, 4H), 1.48-1.21 (m, 4H). Hydrochloride salt: M.p. 190C. Elementalanalyses (%) for C17H22N2O2 HCl Calc. C 63.25; N 8.63; H 7.18, found: C 62.73; N 8.54; H 7.27.

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, N-(5-Bromopentyl)phthalimide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Hebda, Michalina; Bajda, Marek; Wieckowska, Anna; Szal?aj, Natalia; Pasieka, Anna; Panek, Dawid; Gody?, Justyna; Wichur, Tomasz; Knez, Damijan; Gobec, Stanislav; Malawska, Barbara; Molecules; vol. 21; 4; (2016);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem