Tag: M.W=200-300

Synthetic Route of 6941-75-9, These common heterocyclic compound, 6941-75-9, name is 5-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.

To a stirring room temperature solution of 4-bromophthalimide (1.02 g, 4.51 mmol) in dimethylformamide (20 mL) add 60% sodium hydride (0.235 g, 5.87 mmol). Stir this mixture at ambient temperature for 15 minutes and then add iodomethane (0.628 mL, 10.09 mmol). Stir the reaction for 30 minutes at ambient temperature then quench it with brine. Extract the resulting aqueous mixture with ethyl acetate. Wash the combined extracts with brine; dry (sodium sulfate) and concentrate them in vacuo. Purify the resulting material on a flash column (silica gel; 70%-100% CH2C12 gradient in hexanes) to obtain the title compound, 0.960 g (89%). MS (IS+) 7nle 240 (M + H’79Br), 242 (M + H, “Br).

The synthetic route of 6941-75-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/73205; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 675109-26-9, These common heterocyclic compound, 675109-26-9, name is 6-Bromoisoindolin-1-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.

Preparation 124: Methyl 3-(6-bromo-1 -oxo-2,3-dihydro-1 H-isoindol-2-yl)propanoate (1728) To a stirred solution of 6-bromo-2,3-dihydro-1 H-isoindol-1-one (550 mg, 2.59 mmol), 18-crown-6 (69 mg, 0.26 mmol) and methyl 3-bromopropionate (350 pL, 3.1 1 mmol) in DMF (9 ml.) was added CS2CO3 (2.113 g, 6.48 mmol) under nitrogen. The reaction was heated to 70 C (1729) (thermally) slowly and maintained at this temperature for 18 hours. After cooling and the reaction was quenched with NH4CI (sat., aq.). The mixture was extracted with EtOAc (x3) and the combined organic layers were washed with brine, dried over MgSO, filtered and (1730) concentrated under vacuum to yield methyl 3-(6-bromo-1-oxo-2,3-dihydro-1 H-isoindol-2- yl)propanoate as a yellow oil. LC-MS was consistent with a complex mixture which was taken on as is. To the residue was added bis(pinacolato)diboron (0.746 g, 2.91 mmol), AcOK (0.491 mg, 5.00 mmol) and anhydrous 1 ,4-dioxane (8 ml_). The reaction was degassed with nitrogen for 5 minutes. 1 ,1 ‘-Bis(diphenylphosphino)ferrocene-palladium(ll)dichloride dichloromethane complex (61 mg, 0.08 mmol) was then added and the reaction heated at 90C under nitrogen for 16 hours. The reaction was allowed to cool to room temperature and was then diluted with water. The mixture was extracted with EtOAc (x3) and the combined organic layers were washed with brine, dried over MgSO, filtered and concentrated under vacuum to yield the title compound (1.5 g, 168 %) which was used without further purification. MS: [M+H]+ = 346.

The synthetic route of 675109-26-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; BERDINI, Valerio; BUCK, Ildiko Maria; DAY, James Edward Harvey; GRIFFITHS-JONES, Charlotte Mary; HEIGHTMAN, Thomas Daniel; HOWARD, Steven; MURRAY, Christopher William; NORTON, David; O’REILLY, Marc; WOOLFORD, Alison Jo-Anne; COOKE, Michael Liam; COUSIN, David; ONIONS, Stuart Thomas; SHANNON, Jonathan Martin; WATTS, John Paul; (867 pag.)WO2017/68412; (2017); A1;,
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 959235-95-1 as follows. name: 6-(Trifluoromethoxy)indoline

A mixture of 6-(trifluoromethoxy)indoline [CAS 959235-95-1 ] (1 .2 g, 5.89 mmol), 2- (2-(2-(benzyloxy)ethoxy)-4-chlorophenyl)-2-((3-methoxy-5-(1 H-1 ,2,4-triazol-1 – yl)phenyl)amino)acetic acid 6d (2.5 g, 4.91 mmol), HATU (2.29 g, 6.01 mmol) and diisopropylethylamine (1 .99 ml_, 12.0 mmol) in DMF (18 ml_) was stirred at room temperature for 2 h. The mixture was diluted with water. The precipitate was filtered off and washed with water. The precipitate was taken up with EtOAc, washed with a solution of K2CO3 10% in water, water, dried over MgSO4, filtered and the solvent was concentrated under reduced pressure. The compound was purified by flash chromatography on silica gel (15-40 muiotatauiota, 220 g, heptane/EtOAc 50/50). The pure fractions were combined and the solvent was concentrated under reduced pressure to give 2-(2-(2-(benzyloxy)ethoxy)-4-chlorophenyl)-2-((3- methoxy-5-(1 H-1 ,2,4-triazol-1 -yl)phenyl)amino)-1 -(6-(trifluoromethoxy)indolin-1- yl)ethanone 6e (2.5 g).

According to the analysis of related databases, 959235-95-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICALS, INC.; KATHOLIEKE UNIVERSITEIT LEUVEN; KESTELEYN, Bart Rudolf Romanie; BONFANTI, Jean-Francois; COESEMANS, Erwin; RABOISSON, Pierre Jean-Marie Bernard; MARCHAND, Arnaud Didier M; BARDIOT, Dorothee Alice Marie-Eve; (92 pag.)WO2018/178240; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 20780-72-7, 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. 20780-72-7 name is 4-Bromoisatin, 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: A reaction flask with high vacuum valve was charged with 2-amino-N?-arylbenzohydrazides (1.0 mmol), 4-halogenated isatins (1.0 mmol), CuI (10 mg, 0.05 mmol), and Cs2CO3 (650 mg, 2.0 mmol). After being degassed by three freeze-thaw pump cycles, THF (10.0 mL) was injected into the mixture. And then, the reaction mixture was stirred at reflux for 10?16 h before reaching completion, which was monitored by TLC. The solvent was recovered by distillation under reduced pressure, and the residue was purified by chromatography over silica gel to give 3 using ethyl acetate and petroleum ether (1:2) as an eluent.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromoisatin, and friends who are interested can also refer to it.

Reference:
Article; Ma, Yong-Gang; Li, Chao; Yao, Chang-Sheng; Wang, Xiang-Shan; Tetrahedron; vol. 72; 27-28; (2016); p. 3844 – 3850;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 2058-72-2, A common heterocyclic compound, 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, molecular formula is C9H6BrNO2, 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.

The key intermediate 2 was refluxed with equivalent amount ofdifferent isatin derivatives 4a-f or 8a-l in glacial acetic acid. Thereaction was monitored with TLC. After complete of the reaction,the formed solid was collected and washed with water andrecrystallized from DMF/ethanol to get the target compounds 6a-fand 9a-l respectively.

The synthetic route of 2058-72-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Eldehna, Wagdy M.; Abo-Ashour, Mahmoud F.; Nocentini, Alessio; El-Haggar, Radwan S.; Bua, Silvia; Bonardi, Alessandro; Al-Rashood, Sara T.; Hassan, Ghada S.; Gratteri, Paola; Abdel-Aziz, Hatem A.; Supuran, Claudiu T.; European Journal of Medicinal Chemistry; vol. 162; (2019); p. 147 – 160;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 18711-13-2, 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. 18711-13-2, name is 4,7-Dichloroindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of DHEA (0.5 mmol, 1.0 eq) and isatin derivative(0.75 mmol, 1.5 eq) in EtOH (10 mL) was added Al2O3/KF (0.5 mmol,1.0 eq), the resulting mixture was stirred at reflux temperature for 6 h.Upon completion of the reaction indicated by the TLC, the mixture wasfiltered and the solid was washed with dichloromethane (DCM) forseveral times. The filtrate was then evaporated under vacuum, followedby addition of DCM and H2O. The mixture was then acidified with 4MHCl (pH=1-2). The aqueous layer was washed with DCM for severaltimes. The combined organic layers were then dried over Na2SO4 andevaporated under vacuum to the crude product, which was then subjectedto column chromatography, affording the corresponding product.

The chemical industry reduces the impact on the environment during synthesis 4,7-Dichloroindoline-2,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Article; Yang, Yan-Tao; Du, Shuzhang; Wang, Song; Jia, Xuedong; Wang, Xiaojuan; Zhang, Xiaojian; Steroids; vol. 151; (2019);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-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 5332-26-3, Recommanded Product: 2-(Bromomethyl)isoindoline-1,3-dione

(S)-2-{(E)-(S)-1-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-10-oxo-heptadec-2-enyl}-2-hydroxy-succinate To a mixture of No. 5317776 (Compound E; 60 mg, 0.08 mmol), DBU (19 muL, 0.126 mmol) and dichloromethane (0.84 mL) was added 2-bromomethyl-isoindole-1,3-dione (30 mg, 0.126 mmol) commercially available from Aldrich (cat. No. 252611). After the mixture was stirred at room temperature for 6 hours, further 2-bromomethyl-isoindole-1,3-dione (10 mg, 0.04 mmol) and DBU (6.3 muL, 0.04 mmol) were added. Then, 4-(1,3-dioxo-1,3-dihydro-isoindole-2-ylmethyl) 1-butyl (S)-2-{(E)-(S)-1-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-10-oxo-heptadec-2-enyl}-2-hydroxy-succinate (56 mg, 76%) was obtained (ESI (LC/MS positive mode) m/z 873 (M+H); Rt 3.38 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; Chugai Seiyaku Kabushiki Kaisha; KOHCHI, Yasunori; NAKAMA, Kimitaka; KOMIYAMA, Susumu; WATANABE, Fumio; EP2886530; (2015); 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. 5394-18-3, name is 2-(4-Bromobutyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., name: 2-(4-Bromobutyl)isoindoline-1,3-dione

General procedure: A mixture of the intermediates 3a-3e (5 mmol) and corresponding secondary amine 4a-4g (5.5 mmol) was added in CH3CN (20 ml) at the presence of anhydrous K2CO3 (6 mmol). The mixture was heated at 65 C for 6-10 h. The solvent was evaporated in vacuo. The residue was dissolved in CH2Cl2 (25 mL), washed with water (20 mL ¡Á 3), and the combined organic phases were washed with saturated aqueous NaCl (30 mL), dried over sodium sulfate, and filtered. The solvent was evaporated under reduced pressure. The residue was purified on a silica gel chromatography using mixtures of petroleum/acetone as eluent to get the target products TM-1~TM-28.

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; Sang, Zhipei; Wang, Keren; Wang, Huifang; Yu, Lintao; Wang, Huijuan; Ma, Qianwen; Ye, Mengyao; Han, Xue; Liu, Wenmin; Bioorganic and Medicinal Chemistry Letters; vol. 27; 22; (2017); p. 5053 – 5059;,
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. 552330-86-6, name is 5-Bromoisoindolin-1-one, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C8H6BrNO

To R8 (100 mg, 0.47 mmol) in anhydrous dioxane (8 mL) is added R5 (180 mg, 0.71 mmol) and potassium acetate (140 mg, 1.43 mmol). The mixture is purged with Argon, PdCl2(dppf) (40 mg, 0.049 mmol) added and heated to 80 C. for 1.5 h. The reaction mixture is diluted with EA and water, the organic layer washed with brine, dried and concentrated. The crude product is carried on. m/z 260 [M+H]+, rt 0.64 min, LC-MS Method b.

According to the analysis of related databases, 552330-86-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GRUNDL, Marc; OOST, Thorsten; PAUTSCH, Alexander; PETERS, Stefan; RIETHER, Doris; WIENEN, Wolfgang; US2013/172327; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application 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.

Step 2: tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-dihydro-2H-isoindole-2-carboxylate A solution of tert-butyl 5-bromo-1,3-dihydro-2H-isoindole-2-carboxylate (0.80 mmol), bis(pinacolato)diboron (0.96 mmol) and potassium acetate (2.5 mmol) in DMF (4 mL) was degassed. To this solution was added PdCl2dppf (1:1 complex with DCM, 0.04 mmol). The reaction mixture was heated at 85 C. for 4 hr and then allowed to cool to rt and diluted with EtOAc. The solution was washed with water and brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography (10-30% EtOAc in hexane) to give tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-dihydro-2H-isoindole-2-carboxylate (0.57 mmol, 72%) as a white solid. LCMS: (FA) ES+346.

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

Reference:
Patent; Millennium Pharmaceuticals, Inc.; US2008/171754; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem