Tag: M.W=100-200

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, Computed Properties of C8H4ClNO2

General procedure: A mixture of the isatin 1 or acenaphthenequinone 4 (1 mmol), indole 2 (2 mmol), p-TSA (10mol %), CH2Cl2 (10 mL) was added to 50 mL flask and stirred at room temperature until the thecompletion of the reaction (Scheme 1, 2). Then the solid was filtered and washed with CH2Cl2 (5mL) and ethanol (5 mL) in turns, affording the product in excellent yields, which wasrecrystallized from ethanol to produce pure crystalline products. The products were identified byelemental analysis, MS, 1H NMR, 13C NMR, and IR spectra.

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

Reference:
Article; Yu, Jiangxia; Shen, Tianhua; Lin, Yan; Zhou, Yongbing; Song, Qingbao; Synthetic Communications; vol. 44; 14; (2014); p. 2029 – 2036;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 6872-06-6,Some common heterocyclic compound, 6872-06-6, name is 2-Methylindoline, molecular formula is C9H11N, 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: To a solution of compound 65 (0.20g, 0.77mmol) in anhydrous DMF (1mL) was added HATU (0.29g, 0.77mmol), the mixture was stirred at rt for 30min, then DIPEA (0.13mL, 0.77mmol) and p-toluidine (0.083g, 0.77mmol) was added. The mixture was stirred at rt for another 12h and monitored by TLC. Upon completion, the reaction mixture was diluted with water and extracted with EtOAc (3*20mL). The combined organic fractions were washed with brine, dried over Na2SO4, concentrated by evaporation under reduced pressure. Purification by silica gel column chromatography (gradient elution, gradient 0-25% EtOAc/60-90C petroleum ether) gave compound 7 (0.15g, 0.43mmol, 56% yield) as a white solid.

The synthetic route of 6872-06-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Hu, Jianping; Wang, Yingqing; Li, Yanlian; Cao, Danyan; Xu, Lin; Song, ShanShan; Damaneh, Mohammadali Soleimani; Li, Jian; Chen, Yuelei; Wang, Xin; Chen, Lin; Shen, Jingkang; Miao, Zehong; Xiong, Bing; European Journal of Medicinal Chemistry; vol. 150; (2018); p. 156 – 175;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 13220-46-7,Some common heterocyclic compound, 13220-46-7, name is 4-Methylindolin-2-one, molecular formula is C9H9NO, 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 3 3-(3H-Isobenzofuran-1-ylidene)-4-methyl-1,3-dihydro-indol-2-one To a solution containing 4-methyloxindole (0.15 g, 1.02 mmol) and phthalide (0.178 g, 1.33 mmol) in 3.0 mL DMF was added 2.14 mL of sodium hexamethyldisilazane (1.0 M in tetrahydrofuran (THF)) over 1 min. The solution was stirred at room temperature for 30 min and then poured into 50 mL of 4% HCl to give a yellow solid. The aqueous mixture was extracted with EtOAc and the organic phase washed with saturated NaHCO3, H2O, dilute HCl, brine and the solution dried with Na2SO4. The solvent was removed in vacuo and the solid obtained was purified by chromatography (silica gel, CHCl3/EtOAc, 7:3). The solid obtained was recrystallized from EtOAc/hexanes to afford the title compounds (3.8 mg) as a yellow solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Methylindolin-2-one, its application will become more common.

Reference:
Patent; Allergan Sales, LLC; US6541504; (2003); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 32692-19-6, A common heterocyclic compound, 32692-19-6, name is 5-Nitroindoline, molecular formula is C8H8N2O2, 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: We described the synthesis of the compound 1 (Table 2) to illustrate the general procedure for TFA accelerated Petasis three-component reaction. The descriptions of the preparations of all reported compounds are in the Supporting information section. To a magnetically stirred mixture of 5-nitroindoline (0.164 g, 1.0 mmol), 4-tolyboronic acid (0.135 g, 1.0 mmol), and glyoxylic acid monohydrate (0.092 g, 1.0 mmol) in CH2Cl2 (5 ml) was added TFA (20 mul). The mixture was stirred at room temperature for 4 h. After the completion of the reaction (TLC monitoring), half of the solvent was evaporated by means of a rotovap. The resulting solid was filtered through a sintered glass funnel. The collected solid was thoroughly washed with petroleum ether and a small amount of ice water (5 ml), and then dried in vacuo at room temperature for 24 h to afford 0.26 g (83.3 %) of 2-(5-nitroindolin-1-yl)-2-(p-tolyl) acetic acid as a light yellow solid.

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, Jing; Yun, Fan; Xie, Rui; Cheng, Chunhui; Chen, Guangyao; Li, Jingxuan; Tang, Pingwah; Yuan, Qipeng; Tetrahedron Letters; vol. 57; 35; (2016); p. 3916 – 3919;,
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., category: indolines-derivatives

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 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; 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

Reference of 7699-18-5, 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. 7699-18-5 name is 5-Methoxyindolin-2-one, 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.

General procedure: Compounds 8 and 10 were prepared from azo coupling of aryldiazonium salts 3a,b with5-methoxyindolin-2-one 2, previously described [24]. Aryldiazonium salts were prepared startingto corresponding amines (21.5 mmol) in HCl 6N (11 mL) with water solution (7.5 mL) of sodiumnitrite (23 mmol). This solution was added to solution of indol-2-one (21.5 mmol) and sodium acetate(43 mmol) in methanol (59 mL) at 0 C. The resulting precipitate was filtered and purified.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Methoxyindolin-2-one, and friends who are interested can also refer to it.

Reference:
Article; Purgatorio, Rosa; De Candia, Modesto; De Palma, Annalisa; De Santis, Francesco; Pisani, Leonardo; Campagna, Francesco; Cellamare, Saverio; Altomare, Cosimo Damiano; Catto, Marco; Molecules; vol. 23; 7; (2018);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 222036-66-0, name is 5-Aminoisoindolin-1-one, 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 222036-66-0, category: indolines-derivatives

p-TSA monohydrate (23.12 mg, 0.122 mmol) was added to a stirred solution of 1-(4-((2-chloropyrimidin-4-yl)oxy)naphthalen-1 -yl)-3-(1 -(p-tolyl)-3-(tri methylsi lyl)-1 H-pyrazol-5-yl)urea (see Example 6(i) above; 33 mg, 0.061 mmcl) and 5-aminoisoindolin-1-one (18.01 mg, 0.122 mmol) in THFDMF (1 mL, 1:1). The resulting mixture was heated at 60 °C overnight. The reaction was cooled to rt then diluted with EtOAc (15 mL). The suspension was filtered, the product was detected in the filtrate which was subsequentlyconcentrated in vacuo. The crude product was purified by chromatography on silica gel (12 g column, 0-10percent MeOH in DCM) to afford a white solid. The crude product was purified by preparative HPLC (Waters, Acidic (0.1percent Formic acid), Waters X-Select PrepC18, 5 pm, 19×50 mm column, 35-75percent MeCN in Water) to afford the title compound (7 mg) as a white solid.1H NMR (DMSO-d6) 400 MHz, O: 9.93 (s, 1H), 9.24 (s, 1H), 8.84 (s, 1H), 8.47 (d, 1H),8.22 (s, 1H), 8.11 (d, 1H), 8.00 (d, 1H), 7.82-7.80 (m, 1H), 7.65-7.61 (m, 1H), 7.58-7.54(m, 1H), 7.53-7.36 (m, 6H), 7.34-7.25 (m, 2H), 6.70 (d, 1H), 6.65 (s, 1H), 3.99 (s, 2H),2.41 (s, 3H), 0.27 (s, 9H).LCMS mz 655 (M+H)+ (ES+).

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; RESPIVERT LIMITED; TOPIVERT PHARMA LIMITED; FYFE, Matthew, Colin, Thor; MEGHANI, Premji; THOM, Stephen, Malcolm; WO2014/33449; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 14192-26-8, These common heterocyclic compound, 14192-26-8, name is Methyl 2-oxoindoline-6-carboxylate, 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.

Room temperature, 2-indolone-6- methyl formate(5-2) (4.0g, 20 . 71mmol) suspended in 12 ml in toluene of, the chloroactic anhydride (5.4g, 30 . 95mmol) into the above-mentioned suspension, heating reflow 3h, cooling to 80 C, 30 min by adding methyl cyclohexane (6 ml), stirring suspension of cooling to room temperature, filtered to obtain crude products, with cold methanol (4 ml) washing, drying the white solid obtained 5.155g (93.5%), i.e. compound 1-cholroacetyl- 2-indolone-6- methyl formate (6-2).

The synthetic route of 14192-26-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sichuan University; Chen, Yuanwei; Xie, Yongmei; Wei, Yuquan; (32 pag.)CN104003925; (2016); B;,
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. 39603-24-2, name is 5,7-Dimethylindoline-2,3-dione, A new synthetic method of this compound is introduced below., Recommanded Product: 39603-24-2

General procedure: An equimolar mixture of dipolarophile 1/7 (1 mmol), isatin 2a-e/acenaphthenequinone 11 (1 mmol) and sarcosine 3/1,3-thiazolane-4-carboxylic acid 5 (1 mmol) in 2,2,2-trifluoroethanol (10 ml) was refluxed forthe appropriate time (30-40 min). After completion of the reaction asindicated by (TLC), the solid precipitates were filtered and washed withethanol to furnish pure corresponding dispiropyrrolidine/thiapyrrolizidinederivatives. Synthesized compounds were well characterized by 1H NMR, 13CNMR, Mass and single crystal X-ray analysis of representative compounds.

The synthetic route of 39603-24-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Dandia, Anshu; Singh, Ruby; Khan, Shahnawaz; Kumari, Sukhbeer; Soni, Pragya; Tetrahedron Letters; vol. 56; 30; (2015); p. 4438 – 4444;,
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. 50727-04-3, name is 5-Methoxyisoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Computed Properties of C9H7NO3

EXAMPLE 4 4-(1,3-Dioxo-5-methoxy-1,3-dihydroisoindol-2-yl)-2-{1-[2-(4-methoxy-phenyl)-1-(methylcarbamoyl)ethylcarbamoyl]cyclohexylmethyl}butyric acid 4-(1,3-Dioxo-5-methoxy-1,3-dihydroisoindol-2-yl)-2-{1-[2-(4-methoxy-phenyl)-1-(methylcarbamoyl)ethylcarbamoyl]cyclohexylmethyl}butyric acid (mixture of diastereomers) starting with the reaction of 4-hydroxy-2-{1-[2-(4-methoxyphenyl)-1-(methylcarbamoyl)ethylcarbamoyl]cyclohexylmethyl}butyric acid tert-butyl ester with 1,3-dioxo-5-methoxy-1,3dihydroisoindole.

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; Pfizer Inc.; US5854275; (1998); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem