Tag: M.W=200-300

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;,
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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;,
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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;,
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Reference of 201940-08-1,Some common heterocyclic compound, 201940-08-1, name is tert-Butyl 5-bromoisoindoline-2-carboxylate, molecular formula is C13H16BrNO2, 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.

0.69 ml of n-Butyl lithium (2.5M solution in hexane) was added dropwise to a stirred solution of 5- bromo-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester (429 mg; 1.44 mmol) in anhydrous THF (10 ml) at -78C under an atmosphere of nitrogen. The reaction was stirred for 50 minutes then 1-methyl-4-piperidone (212 mul; 1.2 equiv.) was added and stirred at -78C for a further 60 minutes then warmed to room temperature. The reaction was quenched with saturated ammonium chloride solution then extracted with EtOAc. The EtOAc layer was washed with saturated NaHCO3, brine, dried (MgSO4) and evaporated. Purification by flash column chromatography on SiO2, gradient elution from 0% to 10% 2M methanolic ammonia / DCM gave 111 mg of 5-(4-hydroxy-1-methyl- piperidin-4-yl)-1 ,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester as a colourless oil.

The synthetic route of 201940-08-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; WO2008/44029; (2008); A1;,
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Related Products of 6326-79-0, 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. 6326-79-0, name is 6-Bromoisatin belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

As shown in Fig. 133B, a mixture of compound 1 (721 mg, 3.20 mmol, 1.0 eq), compound la (2092) (560 mg, 3.20 mmol, 1.0 eq) and sodium carbonate (866 mg, 8.17 mmol, 2.55 eq) in methanol (10 mL) was stirred at room temperature for 3 h under nitrogen atmosphere. The progress of the reaction mixture was monitored by TLC. After completion of the reaction, the mixture was filtered and the filter cake was washed with methanol and water to afford compound AB17653 (979 mg, 89%) as a red solid. TLC: PE/EA = 3/1, 254 nm; Rf (Compound 1) = 0.6; Rf (Compound AB17653) = 0.4; LC-MS: 338.95 (M-l) ; NMR (400 MHz, d6-DMSO) 511.01 (d, J = 21.5 Hz, 2H), 8.64 (d, J = 8.3 Hz, 1H), 7.62 (d, J = 7.7 Hz, 1H), 7.55 (t, J = 7.6 Hz, 1H), 7.39 (d, J = 8.1 Hz, 1H), 7.18 (d, J = 8.4 Hz, 1H), 7.00 (dd, J = 8.8, 4.6 Hz, 2H).

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, 6-Bromoisatin, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; EINZIGER, Michael; SIMPSON, Ann, Marie; (499 pag.)WO2019/200232; (2019); A1;,
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These common heterocyclic compound, 70478-63-6, name is 4-Bromoisoindoline-1,3-dione, 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 4-Bromoisoindoline-1,3-dione

Step b. A mixture of 7-bromo-3-hydroxy-3-methylisoindolin-l-one and 4-bromo-3-hydroxy-3 -methyl isoindolin-l-one (12.00 g, 49.8 mmol) in DCM (100 ml) was cooled to -40¡ãC. Triethylsilane (80.4 ml, 498 mmol) was added to the reaction mixture at -40¡ãC under N2 atmosphere. Boron trifluoride diethyletherate (18.7 ml, 149.4 mmol) was added to the reaction mixture at -40¡ãC under N2 atmosphere. The reaction mixture was stirred at 0¡ãC for 1 h. The resulting reaction mixture was combined with two other batches prepared on the same scale by an identical method. The resulting reaction mixture was poured into NaHC03 solution (500 ml) and extracted with the DCM (3 x 1000 ml). The combined organic phase was dried over Na2S04, filtered and concentrated under reduced pressure. The crude material obtained was purified by column chromatography (3percent EtOAc in DCM) yielding 7-bromo-3-methylisoindolin-l-one (9.200 g, 40.9 mmol). LCMS: Method A, 1.521 min, MS: ES+ 226.11, 228.11; NMR (400 MHz, CDC13) delta ppm 7.61 (dd, J=7.2, 1.2 Hz, 1 H), 7.43 – 7.38 (m, 3 H), 7.68 – 7.63 (m, 1 H), 1.52 (d, J=6.8 Hz, 3 H).

The synthetic route of 4-Bromoisoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MISSION THERAPEUTICS LIMITED; GIBSON, Karl Richard; JONES, Alison; KEMP, Mark Ian; MADIN, Andrew; STOCKLEY, Martin Lee; WHITLOCK, Gavin Alistair; WOODROW, Michael D; (241 pag.)WO2017/158388; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 4702-13-0, name is N-Phthaloylglycine, 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 4702-13-0, Product Details of 4702-13-0

Typical Procedure: To a 30-mL vial was added N-phthaloylglycine (2.05 g, 10 mmol) and SOCl2 (8 mL) and the vial was sealed. The reaction was stirred in an oil bath at 60 C for 8 h. The mixture was cooled to r.t., the SOCl2 was removed in vacuo, hexane (10 mL) was added, and the mixture was stirred for 10 min resulting in white solid. After filtration, the solid (2.0 g, 90%) was washed with hexane and used directly in the next reaction. Phthaloylglycyl chloride (2.0 g, 9.0 mmol) in CH2Cl2 (8 mL) was added dropwise to the solution of 11a (2.2 g, 7.9 mmol) and Et3N (3.0 mL) in CH2Cl2 (50 mL). The mixture was stirred at r.t. until completion of the reaction, then diluted with CH2Cl2 (150 mL). The organic phase was washed with H2O (3 ¡Á 40mL) and brine, dried (anhyd Na2SO4), and concentrated in vacuo. The residue was purified by flash column chromatography (silicagel) to afford 10a (3.2 g, 89%) as a yellowish solid.

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:
Article; Huang, Liye; Yu, Ruina; Leng, Ling; Gong, Feng; Zhu, Xinhai; Wan, Yiqian; Synthesis; vol. 46; 17; (2014); p. 2317 – 2326;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 2058-72-2, 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.

General procedure: A mixture of compound 3 (1 mmol) and the appropriate isatinderivative 4a-i (1 mmol) in absolute ethyl alcohol and catalyticamount of glacial acetic acid was heated under reflux for 4 hrs,filtered while hot and the collected solid was washed with ethanol.The crude products 5a-i were re-crystallized from ethanol/DMFmixture (3:1) to furnish the pure title compounds 5a-i in 43-94%yields.

The chemical industry reduces the impact on the environment during synthesis 5-Bromo-1-methylindoline-2,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Article; Almutairi, Maha S.; Zakaria, Azza S.; Ignasius, P. Primsa; Al-Wabli, Reem I.; Joe, Isaac Hubert; Attia, Mohamed I.; Journal of Molecular Structure; vol. 1153; (2018); p. 333 – 345;,
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Electric Literature of 667463-64-1,Some common heterocyclic compound, 667463-64-1, name is 6-Bromo-1-methylindoline-2,3-dione, molecular formula is C9H6BrNO2, 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: Synthesis of Intermediate 1-5.2 1-5.1 (15.0 g, 63 mmol) and hydrazine hydrate (30 mL, 618 mmol) are heated to 125 C for 72 h. To the cool reaction mixture DCM is added and extracted with water and 1 M HC1. The organic layer is dried over MgSO4 and concentrated. The crystallized residue is dissolved in DCM, methanol is added and the DCM is removed under vacuum. The crystallized product is filtered withsunction and washed with cold methanol. Yield 63%, m/z 226/228 [M+H]+, rt 1.16 mi LC-MS Method VOOl 003.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Bromo-1-methylindoline-2,3-dione, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ANDERSKEWITZ, Ralf; GRAUERT, Matthias; GRUNDL, Marc; OOST, Thorsten; PAUTSCH, Alexander; PETERS, Stefan; WO2014/140091; (2014); 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. 337536-15-9, name is 4-Bromoisoindolin-1-one, A new synthetic method of this compound is introduced below., Product Details of 337536-15-9

EXAMPLE 54A 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-isoindolinone A suspension of Example 1C (10.6 g, 50 mmol) and 4,4,5,5,4′,4′,5′,5′-octamethyl-[2,2′]bi[[1,3,2]dioxaborolanyl] (15.23 g, 60 mmol) in DMF (390 mL) was stirred until a clear yellow solution was obtained. The solution was then treated with potassium acetate (14.72 g, 150 mmol), degassed with nitrogen, treated with [1.1′-bis(diphenylphosphino)-ferrocene]dichloropalladium [II].CH2Cl2 (7 g, 8.5 mmol) and heated to 90 C. overnight. The reaction was cooled to room temperature and filtered through diatomaceous earth (Celite), and concentrated. The concentrate was partitioned between water and ethyl acetate and filtered through diatomaceous earth (Celite). The organic phase was dried (Na2SO4), filtered, and concentrated. The crude product was purified by silica gel chromatography eluding with 100% ethyl acetate and triturated from hexanes to give 4.56 g (35% yield) of the desired product. m.p.: 189-191 C.

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; Curtin, Michael L.; Davidsen, Steven K.; Frey, Robin R.; Heyman, Howard R.; Holms, James H.; Michaelides, Michael; Steinman, Douglas H.; US2005/26976; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem