Tag: M.W=100-200

Electric Literature of 16078-34-5, The chemical industry reduces the impact on the environment during synthesis 16078-34-5, name is 1-(2,3-Dihydro-1H-indol-5-yl)-ethanone, I believe this compound will play a more active role in future production and life.

Treat a 100 C. solution of 1-indolin-5-ylethanone (1.00 g, 6.02 mmol) in toluene (12 mL) with a solution of di-tert-butyl dicarbonate (1.97 g, 9.03 mmol) in toluene (12 mL) dropwise over 20 minutes. Continue heating the mixture for 30 minutes. Concentrate the reaction mixture. Purify by silica gel column chromatography with 15-35% (1:1 EtOAc:DCM) in hexanes to give the title compound (1.52 g, 97%) as a white solid. ES/MS (m/z): 262.0 (M+H).

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, 1-(2,3-Dihydro-1H-indol-5-yl)-ethanone, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Eli Lilly and Company; Bastian, Jolie Anne; Chen, Jiehao; Cohen, Jeffrey Daniel; Henry, James Robert; McMillen, William Thomas; Reaman, Bradley Earl; Rubio, Almudena; Sall, Daniel Jon; Zhao, Gaiying; (36 pag.)US2017/354641; (2017); A1;,
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Indoline | C8H9N – PubChem

13861-75-1, name is Spiro[cyclopropane-1,3′-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. COA of Formula: C10H9NO

Example 3 1′-((1-isopentyl-1H-benzo[d]imidazol-2-yl)methyl)spiro[cyclopropane-1,3′-indolin]-2′-one A dried flask under nitrogen was charged with sodium hydride (120 mg, 3.0 mmol) and DMF (1 mL). This rapidly stirred suspension was cooled to 0 C. using an ice/water bath and spiro[cyclopropane-1,3′-indolin]-2′-one (160 mg, 1.0 mmol, Preparatory Example 4) was added dropwise as a solution in DMF (2 mL). The ice/water bath was removed for 15 minutes before the mixture was recooled to 0 C. and 2-(chloromethyl)-1-isopentyl-1H-benzo[d]imidazole hydrochloride (236 mg, 1.0 mmol) was added dropwise as a solution in DMF (2.1 mL). The mixture was allowed to warm to rt and stirred there for 16 hours. The mixture was cooled to 0 C. and ice was added carefully. Partition between EtOAc and water was followed by separation, drying and concentration in vacuo. Preparative HPLC gave isolation of the desired compound, (110 mg, 0.31 mmol, 31%). 1H NMR (400 MHz): delta 0.96 (d, 6H), 1.45 (m, 2H), 1.60 (m, 2H), 1.69 (m, 1H), 1.82 (m, 2H), 4.26 (m, 2H), 5.35 (s, 2H), 6.83 (d, 1H), 7.02 (dd, 1H), 7.19 (dd, 1H), 7.29 (m, 3H), 7.47 (d, 1H), 7.81 (m, 1H). LC/MS 360 (MH+).

The synthetic route of 13861-75-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; re: Viral Ltd; Cockerill, Stuart; Pilkington, Christopher; Lumley, James; Angell, Richard; Mathews, Neil; US2014/308282; (2014); A1;,
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Adding a certain compound to certain chemical reactions, such as: 14192-26-8, name is Methyl 2-oxoindoline-6-carboxylate, 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 14192-26-8, Quality Control of Methyl 2-oxoindoline-6-carboxylate

A mixture of compound VI (lOg) and acetic anhydride (40ml) was stirred at about 110C-120C for about 2h. To this reaction mass, triethyl orthobenzoate (35.18gm) was slowly added at about 115-125C for 3h and distilled out low boiler simultaneously at about 120-125C. Then the reaction mass was cooled to about 90C, and concentrated under vacuum to obtain crude compound of formula V.

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Reference:
Patent; GLENMARK PHARMACEUTICALS LIMITED; NAIK, Samir; SRIVASTAVA, Sachin; PATIL, Pramod; PATIL, Premchand Bansilal; BHIRUD, Shekhar Bhaskar; (34 pag.)WO2019/48974; (2019); A1;,
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Electric Literature of 496-12-8,Some common heterocyclic compound, 496-12-8, name is Isoindoline, molecular formula is C8H9N, 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 stirred solution of isoindoline (2 g, 16.8 mmol) at 0 0C5 was added slowly concentrated H2SO4 (10 mL). Then a mixture of 70% HNO3 (2.1 mL, 33.6 mmol) and concentrated H2SO4 (2 mL) was added. After addition the mixture was stirred at 00C for 30 min. The reaction mixture was poured into ice water. The mixture was carefully neutralized with 50% aq. NaOH to pH 10 and extracted with EtOAc (3 x). The combined organic layers were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo to afford 5-nitroisoindoline as a brown solid. LCMS calc. = 165.1; found = 164.9 (M+H)+. 1H NMR (500 MHz5 CDCl3): delta 8.11 (d, J= 8.0 Hz, 2 H); 7.39 (d, J= 7.8 Hz, 1 H); 4.33 (s, 4 H); 2.31 (br s, 1 H).

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

Reference:
Patent; MERCK & CO., INC.; WO2007/81569; (2007); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 17564-64-6, The chemical industry reduces the impact on the environment during synthesis 17564-64-6, name is 2-(Chloromethyl)isoindoline-1,3-dione, I believe this compound will play a more active role in future production and life.

General procedure: The initial carbonyl compound (50 mmol) was dissolved/suspended in ethanol (50 mL) and magnetically stirred with thiosemicarbazide (50 mmol) and catalytic amounts of acetic acid for 8-24 h at room temperature. The obtained thiosemicarbazone was filtered, washed with appropriate solvent (n-hexane, petroleumether or diethyl ether) and dried under vacuum. The intermediate thiosemicarbazone (50 mmol) reacted with ethyl bromoacetate (50 mmol), in methanol (50 mL) and sodium acetate (50 mmol) at room temperature under magnetic stirring for 24 h. The resulting 4-thiazolidinone was poured on ice, filtered or extracted with chloroform (3 x 100 mL) and purified by column chromatography (SiO2, ethyl acetate/n-hexane). Then, the obtained thiazolidinone (50 mmol) was dissolved/suspended in 50 mL of anhydrous acetone in the presence of anhydrous potassium carbonate (50 mmol), and reacted with equimolar amounts of 4-nitrobenzyl bromide, 1-(chloromethyl)naphthalene and N-(chloromethyl)phthalimide for 24-48 h. The product was poured on ice, filtered or extracted with chloroform (3 x 50 mL) and purified by column chromatography (SiO2, ethyl acetate/n-hexane) in order to obtain the title compoundsin high yields. 7.1.58 2-((2-(2-(4-Methylpentan-2-ylidene)hydrazono)-4-oxothiazolidin-3-yl)methyl)isoindoline-1,3-dione (6C) Yellow powder, mp 66-67 C, 75% yield; 1H NMR (400 MHz, DMSO-d6): delta 0.91-0.92 (d, J = 6.8 Hz, 6H, 2 * CH3), 1.91 (s, 3H, CH3), 1.94-2.01 (m, 1H, CH), 2.14-2.16 (d, J = 7.2 Hz, 2H, CH2), 3.82 (s, 2H, CH2, thiazolidinone), 5.73 (s, 2H, ArCH2), 7.74-7.80 (m, 2H, Ar), 7.86-7.88 (m, 2H, Ar).

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, 2-(Chloromethyl)isoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; De Monte, Celeste; Carradori, Simone; Bizzarri, Bruna; Bolasco, Adriana; Caprara, Federica; Mollica, Adriano; Rivanera, Daniela; Mari, Emanuela; Zicari, Alessandra; Akdemir, Atilla; Secci, Daniela; European Journal of Medicinal Chemistry; vol. 107; (2016); p. 82 – 96;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 56341-37-8, name is 6-Chlorooxindole, 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 56341-37-8, COA of Formula: C8H6ClNO

6-Chloroindolin-2-one (8.35 g, 50 mmol) and 3-chloro-2-fluorobenzaldehyde (8.295 g, 52.5 mmol) were stirred at reflux in the presence of piperidine (1 ml) for 6 hours. The reaction suspension was then filtered, and the solid obtained was washed with methanol and dried to give a yellow solid product, (E)-6-chloro-3-(3-chloro-2-fluorobenzylidene)indol2-one (14.63g, 47.5mmol). Yield: 95%. 1H NMR (400MHz, DMSO): delta 10.85 (s, 1 H), 7.70 (q, J=7.3Hz 2 H), 7.54 (s, 1 H), 7.36 (t, J=8Hz 1 H), 7.16 (d, J=8Hz 1 H), 6.92-6.86 (m, 2 H); MS: Calcd for C15H9Cl2FNO ([M+H]+): 308, found: 308.0.

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; Xiao, Fei; MA, Jie; XIAO, Fei; REN, Hongjun; WANG, Wei; XU, Hongtao; WANG, Meng; ZOU, Lihui; DING, Fei; SU, Fei; (41 pag.)EP3498712; (2019); 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. 324-03-8, name is 6-Fluoroindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 6-Fluoroindoline-2,3-dione

Exampie 1; 7-fluoro-3-hvdroxvquinolin-2{1H)-one; The title compound was prepared by the procedure depicted Sn Scheme 1 and described in detail below, using the general method of S-Y. Sit et al., Bioorqanic Medicinal Chem Lett.1996, beta, 499. Step 1. 6-Fluoro-1H-indo.e-2,3-dione (6-fluoroisatin, 200 mg, 1.2 mMoi), diethylamide (0.24 ml. 2.3 mMol), and ethyl diazoacetate (0,24 mL 2.3 mMol) were dissolved in ethanoi (15 mL) and stirred at room temperature for 64 hours. Removal of solvent in vacuo then provided the diazo intermediate as an Oil (LCMS m/z 278.0 [M-1]); this was treated with hydrochloric acid (1N, 75 rnL), and allowed to react for 40 hours at room temperature Filtration of the reaction mixture yielded ethyl 7-f.uoro-3- hydroxy-2-oxo-1.2-dihyo’roquinoiine-4-carboxylate as an orange solid (144 mg, 0.57 mMol). LCMS m/z 252.1 (M+1). 1H NMR (400 MHz, CD3OD) delta 1.42 (t, J^7,0 Hz13H), 4.48 (q, J =7.0 Hz, 2H)8 7.02 (m, 2H), 7.87 (del. J =5.6. 8.9 Hz, 1H).

The synthetic route of 324-03-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; DUPLANTIER, Allen Jacob; GAN, Xinmin; HU, Lain-Yen; LU, Jiemin; SHEEHAN, Susan Mary Kult; WO2010/58314; (2010); 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. 84575-27-9, name is 7-Methoxyindoline-2,3-dione, A new synthetic method of this compound is introduced below., Product Details of 84575-27-9

To a stirring suspension of 7-methoxyindoline-2,3-dione (11 g, 64 mmol) in water (64 ml) was added potassium hydroxide (5.5 g, 80 mmol). The reaction mixture was stirred at 40C for 5h. The reaction mixure was allowed to cool to room temperature, the precipitate was removed through filtration and the filtrate lyophilized to give the title compound as a white solid. The product was used without purification in the next step. LC/MS = 196 [M+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; MERCK SHARP & DOHME CORP.; ALI, Amjad; ZHOU, Gang; KUANG, Rongze; LIM, Yeon-Hee; LO, Michael Man-Chu; TING, Pauline, C.; BIJU, Purakkattle; RUIZ, Manuel de Lera; DEGRADO, Sylvia, J.; TUNG, Alexander, L.; HENDERSON, Timothy, J.; HONG, Liwu; KIM, Jae-Hun; KIM, David Won-Shik; LEE, Joe, F.; WU, Jie; WU, Heping; XIAO, Yushi; YU, Tao; ZHU, Xiaohong; MCCORMICK, Kevin, D.; TAGAT, Jayaram, R.; XIAO, Dong; KHAN, Tanweer; CAO, Jianhua; BERLIN, Michael; ZHANG, Yonglian; (80 pag.)WO2016/126570; (2016); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 39603-24-2, name is 5,7-Dimethylindoline-2,3-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 39603-24-2, Computed Properties of C10H9NO2

General procedure: To a round bottom flask containing 5 ml glycerol was added respective isatin (1 mmol) and respective thiosemicarbazide/semicarbazide (1 mmol) under stirring. The temperature of the reaction was set at 40 oC and the resulting mixture was stirred till completion and progress of reaction was monitored with TLC (Hexane/EtOAc 2:1). The reaction was quenched with hot water whence glycerol got dissolved in water and the resulting insoluble solid precipitate was filtered and dried to obtain the crude product which was as good as pure (1H NMR). The aqueous phase containing glycerol was extracted with methyl t-butyl ether (4 ¡Á 25 mL) to remove any trace of organic compounds and then evaporated in vacuo to give pure glycerol which was used for the next cycle.

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, 5,7-Dimethylindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Tiwari, Jyoti; Saquib, Mohammad; Singh, Swastika; Tufail, Fatima; Singh, Jaya; Singh, Jagdamba; Synthetic Communications; vol. 47; 21; (2017); p. 1999 – 2006;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

13220-46-7, name is 4-Methylindolin-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. SDS of cas: 13220-46-7

5-Bromo-4-methyloxindole and 5,7-Dibromo-4-methyloxindole 4-Methyl-2-oxindole (5 g) in 40 mL of acetonitrile was treated with 7.26 g of N-bromosuccinimide and stirred at room temperature for 4 hours. Thin layer chromatography (ethyl acetate:hexane 1:2, silica gel) showed a mixture of 5-bromo (Rf 0.3) and 5,7-dibromo (Rf 0.5) products. Another 7.26 g of N-bromosuccinimide was added and the mixture stirred for 4 additional hours. The solid was collected by vacuum filtration, washed with 20 mL of acetonitrile and dried to give a 1:1 mixture of mono and dibromo compounds. The filtrate was concentrated and chromatographed on silica gel (ethyl acetate:hexane (1:2)) to give 1.67 g of 5-bromo-4-methyl-2-oxindole as a beige solid. The remaining 1:1 mixture of solids was recrystallized twice from glacial acetic acid to give 3.2 g of 5,7-dibromo-4-methyl-2-oxindole as a light orange solid. The filtrates from this material were chromatographed as above to give 0.6 g of 5-bromo-4-methyl-2-oxindole and 0.5 g of 5,7-dibromo-4-methyl-2-oxindole.

The synthetic route of 13220-46-7 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