Tag: M.W=100-200

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. 3484-35-3, name is 5-Methylindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., Formula: C9H9NO

General procedure: To a solution of 3-substituted-5-benzylidene-2-thioxo-4-thiazolidinone (1-19) (0.003 mol) in 1,4-dioxane (15 mL) was added HC(OEt)3(2 mL) and BF3Et2O (2 mL). The reaction mixture washeated to 80 C and stirring was continued at the same temperature for 4 h. Theresulting 2-ethylthio-3-substituted-5-benzylidene- 4-thiazolium fluoroborate (Ic, IIc) was precipitated, filteredoff, and dried without any additional purification, as starting material forthe following reactions. To a mixture of thiazolium fluoroborate (Ic, IIc) (0.003 mol) and correspondingindolin-2-one (0.003 mol) in acetonitrile (15 mL) was added triethylamine (0.91g, 0.009 mol) dropwise at 25 C, and the mixture was stirred for 4 h at thesame temperature. The orange precipitate was collected and washed with ethylacetate (8 mL). The crude product thus obtained was recrystallized from methanol or acetone to give compound (1-19).

According to the analysis of related databases, 3484-35-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wang, Feng; Liu, Zijian; Wang, Jian; Tao, Jun; Gong, Ping; Bao, Xue; Zhao, Yanfang; Wang, Yulin; European Journal of Medicinal Chemistry; vol. 101; (2015); p. 126 – 132;,
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Related Products of 56341-37-8, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 56341-37-8 name is 6-Chlorooxindole, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

[Step 1] (3E/Z)-6-chloro-3-[(2-chloro-3-fluoropyridin-4-yl)methylene]-1,3-dihydro-2H-indol-2-one [0083] N,N-Diisopropylethylamine (0.46 ml, 2.63 mmol) was added to a methanol (130 ml) solution of 6-chloro-1,3-dihydro-2H-indol-2-one (2.20 g, 13.11 mmol) and 2-chloro-3-fluoroisonicotinaldehyde (2.20 g, 13.8 mmol) and the resulting mixture was heated to reflux for 16 hours. After cooling, the precipitate was collected by filtration, washed with cold methanol and dried to give 3.37 g (83%) of the title compound as a solid. MS (APCI) m/z: 309 (M+H)+.

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

Reference:
Patent; Daiichi Sankyo Company, Limited; YOSHIDA, Shoko; SUGIMOTO, Yuuichi; EP2894156; (2015); A1;,
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

4-(2-Carboxyethyl)-2-formyl-3-methylpyrrole (90 mg), 74 mg 4-methyl-2-oxindole, and 75 muL piperidine in 2 mL of ethanol were heated at 95 C. for 5 hours. The reaction mixture was cooled and concentrated. The residue was suspended in 6 N aqueous hydrochloric acid. The precipitate was filtered, washed with water to pH 6 and dried in a vacuum oven to give 80 mg (52%) of the title compound as a brown solid.1HNMR (360 MHz, DMSO-d6): delta 13.33 (s, br, 1H, NH-1′), 10.84 (s, br, 1H, NH-1), 7.54 (s, 1H, H-vinyl), 7.12 (d, J=2.0 Hz, 1H, H-2′), 7.01 (t, J=7.75 Hz, 1H, H-6), 6.79 (d, J=7.75 Hz, H-5), 6.74 (d, J=7.75 Hz, 1H , H-7), 2.64 (t, J=7.65 Hz, 2H, CH2CH2COOH), 2.57 (s, 3H, CH3), 2.42 (t, J=7.65 Hz, 2H, CH2CH2COOH), 2.19 (s, 3H, CH3); MS m/z (relative intensity, %) 311 ([M+1]+, 100).

The synthetic route of 13220-46-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sugen, Inc.; US6878733; (2005); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 21857-45-4, These common heterocyclic compound, 21857-45-4, name is 5-Methoxyindoline, 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.

Step 2: To a solution of 3-(4-nitro-1 H-pyrazol-1-yl)propanal (200 mg, 1 .18 mmol) in MeOH (12.0 mL), 5-methoxyindoline (176 mg, 1 .18 mmol) was added. This reaction mixture was stirred at rt for 1 h, then NaBH4 (121 mg, 3.20 mmol) was added and stirred for another 30 min at rt. The reaction mixture was quenched with water and extracted with EtOAc (2x). The combined org. layers were dried (MgS04), filtered and the solvent was removed under reduced pressure to yield 5-methoxy-1-(3-(4-nitro-1 H-pyrazol-1 -yl)propyl)indoline, which was used in the next step without further purification. LC-MS conditions B: tR = 0.56 min, [M+H]+= 303.15.

Statistics shows that 5-Methoxyindoline is playing an increasingly important role. we look forward to future research findings about 21857-45-4.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; BOLLI, Martin; BOSS, Christoph; BROTSCHI, Christine; GUDE, Markus; HEIDMANN, Bibia; SIFFERLEN, Thierry; WILLIAMS, Jodi, T.; WO2012/110986; (2012); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 324-03-8, name is 6-Fluoroindoline-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 324-03-8, category: indolines-derivatives

To a stirred solution of starting material E-1.1-6 (55.0 g; 333.1 mmol) in DMF (550 ml_) is added K2CO3 (55.2 g; 399.7 mmol) and 2-iodo-propane (73.6 g; 433.0 mmol) at 25 C. The reaction mixture is stirred at 25 C for 16 h. Then the mixture is diluted with water and extracted with ethyl acetate. The organic layer is concentrated under reduced pressure to obtain crude compound. The crude is purified by column chromatography using silicagel (230-400 pm) with eluting mixture of ethyl acetate and hexane. Yield: 51 % (35.0 g; 169.0 mmol) HPLC-MS: (M+H)+ = 208; tRet = 2.02 min; method RND-FA-4.5-MIN

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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; TONTSCH-GRUNT, Ulrike; BAUM, Anke; RUDOLPH, Dorothea Ingrid; (85 pag.)WO2019/145410; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 14192-26-8, 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. 14192-26-8, name is Methyl 2-oxoindoline-6-carboxylate belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a 25 mL round bottomed flask was added different substituted oxindoles 8 (0.2 mmol, 1.0 equiv.) and bromoethylsulfonium salt 9 (132.99 mg, 0.3 mmol, 1.5 equiv.), DMF (2 mL). The mixture was stirred at room temperature for 5min and Et3N (61.88 mg, 0.6 mmol, 3.0 equiv.) was added into reaction system. The mixture was stirred for 6h at room temperature until the reaction completed, quenched with saturated ammonium chloride solution (5 mL), and was extracted with EtOAc (3×30 mL). The combined organic layer washed with H2O (2×10 mL), dried with anhydrous sodium sulfate. After concentration, product was purified using column chromatography on silica gel with suitable eluent.

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, Methyl 2-oxoindoline-6-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Qin, Hui; Miao, Yuanyuan; Zhang, Ke; Xu, Jian; Sun, Haopeng; Liu, Wenyuan; Feng, Feng; Qu, Wei; Tetrahedron; vol. 74; 47; (2018); p. 6809 – 6814;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 114041-16-6, 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. 114041-16-6, name is 5,6-Dimethoxyisoindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Compound 8 (70.6 mg, 0.24 mmol) and 5,6-dimethoxyisoindoline(68.5 mg, 0.38 mmol) were dissolved in CH3CN (30 mL), followed by addition of K2CO3 (138.8 mg, 1.00 mmol). The mixture was heated under reflux and stirred at 90 C for 6 h. After cooling and filtration, the solvent was removed under reduced pressure. The residue was purified by silica gel chromatography (petroleum ether/ethyl acetate/triethyamine) = 10:10:1, v/v/v) to afford 13(56.8 mg, 59%)

The synthetic route of 5,6-Dimethoxyisoindoline has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Liang; Ye, Jiajun; He, Yingfang; Deuther-Conrad, Winnie; Zhang, Jinming; Zhang, Xiaojun; Cui, Mengchao; Steinbach, Joerg; Huang, Yiyun; Brust, Peter; Jia, Hongmei; Bioorganic and Medicinal Chemistry; vol. 25; 14; (2017); p. 3792 – 3802;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 60434-13-1, 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. 60434-13-1, name is 5-Chloro-1-methylindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A mixture of substituted isatin (12.3 mmol), hydrazine hydrate (368 mmol), potassium hydroxide (245 mmol), and ethylene glycol (242 mmol) were heated at 100 C for 1 h. The reaction mixture was cooled on ice bath and acidified using concd HCl (drop wise addition) along with vigorous stirring. The precipitated product was vacuum filtered and washed with hexanes to give substituted indolin-2-ones in 90-95% yield.

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-Chloro-1-methylindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Jha, Mukund; Chou, Ting-Yi; Blunt, Brian; Tetrahedron; vol. 67; 5; (2011); p. 982 – 989;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 17564-64-6, 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. 17564-64-6, name is 2-(Chloromethyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

Butanethiol (902 mg, 10 mmol), carbon disulfide (761 mg, 10 mmol), and THF (5 mL) were placed in 25 mL round-bottomed flask. A solution of KOH (561 mg, 10 mol) in 3 mL of water was added dropwise under stirring at room temperature. The resulting solution was stirred at room temperature for a further 15 min. Then the solution was added slowly into a solution of N-(chloromethyl)phthalimide (1.96 g, 10 mmol) in acetone (10 mL). The reaction mixture was stirred for 30 min. After removal of the solvent, the residue was diluted with ethyl acetate (100 mL). The solution was washed sequentially with water (2*50 mL) and saturated brine (2*50 mL), dried over anhydrous Na2SO4, and the solvent was removed by rotary evaporation, the residue was recrystallized from a mixture of petroleum ether and ethyl acetate to give S-[(1-tert-butoxycarbonylamino-4-phthalimido)butan-2-yl] S’-butyl trithiocarbonate (1k) as yellow crystals 2.86 g, 88% yield, mp: 89-91 C. Lit. 17 89-91 C. 1H NMR (CDCl3, 400 MHz) (delta, ppm) 0.93 (t, J=7.2 Hz, 3H, CH3), 1.42 (hextet, J=7.2 Hz, 2H, CH2), 1.64-1.72 (m, 2H, CH2), 3.37 (t, J=7.2 Hz, 2H, CH2), 5.65 (s, 2H, CH2), 7.75 (dd, J=5.2, 3.0 Hz, 2H, ArH), 7.87 (dd, J=5.2, 3.0 Hz, 2H, ArH). 13C NMR (CDCl3, 101 MHz) (delta, ppm) 13.5, 22.0, 29.8, 36.9, 41.9, 123.7, 131.8, 134.4, 166.6, 220.8.

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

Reference:
Article; Huang, Zhongyan; Xu, Jiaxi; Tetrahedron; vol. 69; 48; (2013); p. 10272 – 10278;,
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. 3676-85-5, name is 5-Aminoisoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., name: 5-Aminoisoindoline-1,3-dione

(a) 4-Methanesulfonamidophthalimide Methanesulfonylchloride (2.6 ml, 0.034 mol) was added dropwise to a stirred suspension of 4-aminophthalimide (5.0 g, 0.031 mol) in pyridine (50 ml). The mixture was stirred for 48 h under N2 at room temperature, after which time the solid formed was isolated by filtration, washing well with H2 O and CH2 Cl2 and then dried in vacuo to afford the subtitle compound as a colourless solid (5.67 g, 76%). Rf 0.52 (CH2 Cl2/MeOH/0.88NH3 90/10/1, v/v). MS m/z 241 (MH+).

According to the analysis of related databases, 3676-85-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pfizer Inc.; US6103738; (2000); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem