Month: September 2021

Related Products of 20870-90-0, A common heterocyclic compound, 20870-90-0, name is 5-Bromo-1-methyl-2-oxoindoline, molecular formula is C9H8BrNO, 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: A mixture of 5-bromo-1-methyl-1,3-dihydro-2H-indol-2-one (1 g, 4 mmol) [Maybridge, cat10430564], 4,4,5,5,4?,4?,5?,5?-octamethyl-[2,2?]bi[[1,3,2]dioxaborolanyl] (1.7 g, 6.6 mmol), [1,1?-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complexed with dichloromethane (1:1) (200 mg, 0.2 mmol) and potassium acetate (1.3 g, 13 mmol) in 1,4-dioxane (40 mL) was purged with nitrogen and then stirred at 90 C. overnight. After cooling to room temperature, the reaction mixture was concentrated. The residue was purified by flash chromatography eluting with 0 to 25% EtOAc in hexanes to give the desired product. LC-MS calculated for C15H21BNO3 (M+H)+: m/z=274.1. found 274.1.

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; Incyte Corporation; Wu, Liangxing; Konkol, Leah C.; Lajkiewicz, Neil; Lu, Liang; Xu, Meizhong; Yao, Wenqing; Yu, Zhiyong; Zhang, Colin; He, Chunhong; (107 pag.)US2016/9712; (2016); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 61-70-1, These common heterocyclic compound, 61-70-1, name is 1-Methylindolin-2-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.

To a 5 L 4-neck flask (equipped with a mechanical stirrer, condenser, N2 inlet and NAOH scrubbing solution) was charged sequentially with carbon disulfide (CS2) (1.5 L), anhydrous aluminum chloride (AIC13) (2.7 mol, 359 g, 6 equiv) and CHLOROACETYL chloride (0.585 mol, 66.1 g (46.6 mL), 1.3 equiv). 1- methyl-1, 3-dihydroindol-2-one (0.45 mol, 66.2 g, 1 equiv) was added portionwise over 1 hour; the addition was accompanied with temperature increase of 20–> 310 C. After the addition of 1-methyl-1, 3-dihydroindol-2-one was complete the reaction mixture was stirred 0.75 hour at which time stirring of the reaction mixture was not possible. The reaction mixture was refluxed for 3.5 hours then cooled to room temperature. The carbon disulfide (CS2) was decanted, the residue cooled in an ice/water bath. The reaction mixture was quenched by very slow addition of ice and water. The resulting tan suspension was stirred overnight at room temperature. The solids was collected, washed with water (4X), dried on the filter for 15 min followed by drying overnight in hood. The product was further dried in a vacuum oven at- 50 C for 24 hours; the product was pulverized and dried in a vacuum oven for an additional 3 hours AT-70 C to give 91.6 g (91%) of 5-(2-CHLOROACETYL)-1- METHYL-1, 3-dihydroindol-2-one of a salmon colored solid, mp 197-200 C.

The synthetic route of 61-70-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WARNER-LAMBERT COMPANY LLC; WO2004/37820; (2004); 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

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

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

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

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

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

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

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