Author: Jessica.F

These common heterocyclic compound, 7699-18-5, name is 5-Methoxyindolin-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. Quality Control of 5-Methoxyindolin-2-one

B. (E)-3-((3-(4-((dimethylamino)methyl)styryl)-l-((2-(trimethylsilyl)indazol-6-yl)methylene)-5-methoxyindolin-2-one[00108] Piperidine (0.01 mL, 0.1 mmol) was added to a solution of 5-methoxyoxindole (52 mg, 0.32 mmol) and (E)-3-(4-((dimethylamino)methyl)styryl)-l-((2- (trimethylsilyl)ethoxy)-methyl)-lH-indazole-6-carbaldehyde (contaminated with TBAF from previous deprotection attempt, 95.5 mg, 0.22 mmol) in EtOH (5 mL). The reaction was then heated to 75C for 25 hrs. The solvent was evaporated in vacuo. Chromatography (5g silica SPE tube, Silicycle, 5-10% MeOH in CH2C12) gave a brown oil (105 mg, contained product and TBAF by NMR). The residue was dissolved in EtOAc (100 mL) and washed with brine (3 x 15 mL), dried over Na2S04 and the solvent was evaporated in vacuo to give the title compound as a brown oil (1 lOmg, used without further purification).

The synthetic route of 5-Methoxyindolin-2-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY HEALTH NETWORK; SAMPSON, Peter Brent; LIU, Yong; LI, Sze-Wan; FORREST, Bryan T.; PAULS, Heinz W.; EDWARDS, Louise G.; FEHER, Miklos; PATEL, Narendra Kumar B.; LAUFER, Radoslaw; PAN, Guohua; WO2011/123946; (2011); A1;,
Indoline – Wikipedia,
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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. 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 5-Bromo-1-methylindoline-2,3-dione

General procedure: A solution of isatins 1 (0.6 mmol), 3-methyl-4-nitro-5-isatylidenylisoxazoles 2 (0.4 mmol) and proline or thioproline (0.8 mmol) in the 10.0 mL of EtOH at reflux for 5 h. After completion of the reaction, as indicated by TLC, the reaction mixture was directly subjected to flash column chromatography on silica gel (petroleum ether/EtOAc = 5:1-3:1) to furnish the corresponding products 3.

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 2058-72-2.

Reference:
Article; Lin, Bing; Zhang, Wen-Hui; Wang, Dan-Dan; Gong, Yi; Wei, Qi-Di; Liu, Xiong-Li; Feng, Ting-Ting; Zhou, Ying; Yuan, Wei-Cheng; Tetrahedron; vol. 73; 34; (2017); p. 5176 – 5188;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 480-91-1 as follows. name: Isoindolin-1-one

A mixture of isoindolin-1-one (150 mg, 1.13 mmol), 1D (300 mg, 1.13 mmol), Pd2(dba)3 (31 mg, 0.034 mmol), Xantphos (20 mg, 0.034 mmol) and Cs2CO3 (443 mg, 1.36 mmol) in dioxane (25 mE) was heated to 100 C. for 16 hours under a nitrogen atmosphere. The reaction mixture was allowed to cool to room temperature, filtered and the resulting filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (1-5% MeOH in DCM) to afford compound 1 (270 mg, 75% yield) as an off-white solid: ?H NMR (400 MHz DMSO-d5) oe 8.71 (s, 1H), 8.64 (d, J=8.4 Hz, 1H), 8.07 (t, J=8 Hz, 1H), 7.88-7.83 (m, 2H), 7.72 (d, J=8.4 Hz, 2H), 7.59-7.53 (m, 1H), 5.18 (s, 2H), 4.12-4.07 (m, 1H), 1.14-1.09 (m, 2H), 1.0-0.95 (m, 2H); ESI mlz 318.1[M+1].

According to the analysis of related databases, 480-91-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Seal Rock Therapeutics, Inc.; BROWN, Samuel David; US2018/291002; (2018); 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. 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, A new synthetic method of this compound is introduced below., SDS of cas: 2058-72-2

General procedure: A solution of isatins 1 (0.3 mmol), 4-methylpent-3-en-2-one 2 (0.4 mmol), 10 mol% of Et2NH in 3.0 mL of MeOH at 25 C for 24 h. Then, tartaric acid (40 eq) and HCl (6 N, 10 muL) were added at reflux for 12 h. After the completion of reaction, as indicated by TLC, the removal of solvent and purification by flash column chromatography (hexane/EtOAc 8:1?6:1) were performed to furnish the corresponding products 3.

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; Zhou, Gen; Wei, Qi-Di; Wang, Guan-Lian; Gong, Yi; Liu, Huan-Huan; Liu, Xiong-Li; Chen, Lin; Zhou, Ying; Synthetic Communications; vol. 48; 9; (2018); p. 1033 – 1039;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 550-44-7, 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. 550-44-7, name is 2-Methylisoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

1) Production of 1,1,2,3,3-pentamethylisoindoline: With cooling with ice, 1.40 g of zirconium chloride was added to 6.0 mL of a THF solution of 483 mg of N-methylphthalimide, and stirred for 30 minutes with cooling with ice. 18.7 mL of 0.96 M methylmagnesium chloride/THF solution was added to it, and stirred at room temperature for 18 hours. With cooling with ice, 20 mL of aqueous 5 M sodium hydroxide solution was added to the reaction liquid, and extracted with chloroform. The organic layer was dried with anhydrous sodium sulfate, and the solvent was evaporated away under reduced pressure. The crude product was purified through NH silica gel column chromatography (hexane/ethyl acetate) to obtain 105 mg of the entitled compound as a yellow solid. 1H-NMR (400 MHz, CDCl3) delta: 7.25-7.20 (2H, m), 7.17-7.13 (2H, m), 2.42 (3H, s), 1.33 (12H, s) ESI-MS Found: m/z [M+H]+ 190

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-Methylisoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Banyu Pharmaceutical Co., Ltd.; EP2168966; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 4702-13-0,Some common heterocyclic compound, 4702-13-0, name is N-Phthaloylglycine, molecular formula is C10H7NO4, 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 amino-acid phthalyl derivative(0.001 mol) and thionylchloride (6 mL) was refluxed for 3 h at 50C. The excess of thionylchloride was vacuum distilled.Anhydrous toluene was added to the reaction flask and distilled off in vacuo three times for complete removal of thionylchloride.Then, obtained chlorides 2 and 3 were used for acylation.

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

Reference:
Article; Gabbasov; Tsyrlina; Spirikhin; Yunusov; Chemistry of Natural Compounds; vol. 54; 5; (2018); p. 951 – 955; Khim. Prir. Soedin.; 5; (2018); p. 806 – 809,4;,
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. 825-70-7, name is 5-Fluoro-2-methylindoline, A new synthetic method of this compound is introduced below., Formula: C9H10FN

5-Fluoro-2-methylindoline 16a (1.30 g, 8.60 mmol, prepared according to the known method disclosed in “”) and 3b (1.47 g, 8.60 mmol) were dissolved in 40 mL of dichloromethane successively, and stirred for 2 hours. The reaction solution was then added with sodium triacetoxyborohydride (2.73 g, 12.90 mmol), and reacted for 12 hours after addition. The reaction solution was poured into 50 ml of water, and the water phase was extracted with dichloromethane (50 mL*2). The organic phases were combined, dried over anhydrous sodium sulfate, and filtered.

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; Jiangsu Hengrui Medicine Co., Ltd.; Shanghai Hengrui Pharmaceutical Co., Ltd.; LI, Xin; HE, Wei; WANG, Bin; ZHANG, Zhigao; HE, Feng; TAO, Weikang; (104 pag.)EP3560918; (2019); A1;,
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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. 356068-93-4, name is (Z)-5-((5-Fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid, A new synthetic method of this compound is introduced below., Quality Control of (Z)-5-((5-Fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid

Step 5c. (Z)-Methyl 4-(2-(5-((5-fluoro-2-oxoindolin-3-ylidene)methyl)-2,4- dimethyl-lH- pyrrole-3-carboxamido)ethoxy)benzoate (Compound 203)To a stirred solution of compound 109 (0.5 g, 1.67 mmol) in TetaF (150 mL) at00C was added etaOBt (0.34 g, 2.8 mmol), triethylamine (0.6 mL, 4.18 mmol),ECDI-etaC1 (0.48 g, 2.8 mmol) and compound 202 (0.6 g, 3.33 mmol) successively. The mixture was stirred overnight at room temperature, evaporated to remove solvent, diluted with water (50 mL), brine (50 mL) and saturated sodium bicarbonate solution (50 mL). The peta of solution was adjusted to 11-12 with 1OM NaOH. The mixture was filtered, washed with water, dried to obtain crude yellow solid 203 (550 mg, 69%). LCMS: 478 [M+lf, 1H NMR (DMSCM6): delta 2.40 (s, 3H), 2.43 (s, 3H), 3.63 (m, 2H),3.82 (s, 3H), 4.20 (t,2H), 6.92 (m, 2H), 7.07 (d, 2H), 7.70 (m, 2H), 7.84(s, 1H),7 .91 (d, 2H), 10.88 (s, IH), 13.68 (s, IH).

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; CURIS, INC.; WO2008/33743; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 16800-68-3, name is 1-Acetylindolin-3-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 16800-68-3, Quality Control of 1-Acetylindolin-3-one

N-Ethylindole (1.35 g, 10 mmol) and iodine (2.53 g, 10 mmol) were dissolved in ethanol and heated to 80 C. The reaction mixture of 24 After an hour, the extract was extracted with dichloromethane and the organic layers were combined, dried over anhydrous sodium sulfate and recrystallized from dichloromethane / methanol to give N-acetyl-3- (N-ethylindole-3) -indole as a white solid 2.89 g, yield 95%

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; Sun Yat-sen University; Weng, Jiang; Lu, Gui; Guo, Jing; (7 pag.)CN105669516; (2016); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 200049-46-3, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 200049-46-3 as follows.

[00259] A stirred mixture of Int-A (200 mg, 0.984 mmol), 7-bromoisoindolin-l-one 1 (240 mg, 1.13 mmol), XPhos (47 mg, 0.098 mmol), Cs2C03 (800 mg, 2.46 mmol), and fert-butanol (7.8 mL) at rt, was purged with a stream of argon for 5 min. Pd2(dba)3 (90 mg, 0.098 mmol) was added and the vial was sealed and heated at 100 C for 16 h. The mixture was cooled to rt and concentrated under reduced pressure. The residue was partitioned between DCM and water. The organic layer was separated and the aq layer re-extracted with additional DCM. The combined organic layers were dried (Na2S04), filtered, and concentrated under reduced pressure. The residue was purified via reverse-phase preparative HPLC (X-Select CSH C18 250 chi 19 mm, 5mupiiota column; eluting with 10-90% MeCN/H20 containing 0.05% TFA, over 30 min) to afford compound 2 (52 mg, 12%) as a yellow solid. LCMS Mass: 335.0 (M++l).

According to the analysis of related databases, 200049-46-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SIDECAR THERAPEUTICS, INC.; ROWBOTTOM, Martin W.; HUTCHINSON, John. H.; (178 pag.)WO2019/70742; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem