Category: indolines-derivatives

Synthetic Route 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.

I-3.1 (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 HCl. The organic layer is dried over MgSO4 and concentrated. The crystallized residue is dissolved in DCM, methanol is added and the DCM is removed in vacuo. The crystallized product is filtered by sunction and washed with cold methanol. Yield 63%, m/z 226/228 [M+H]+, rt 1.16 min, LC-MS Method V001-003.

The synthetic route of 667463-64-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GRAUERT, Matthias; ANDERSKEWITZ, Ralf; GRUNDL, Marc; OOST, Thorsten; PAUTSCH, Alexander; PETERS, Stefan; US2014/275155; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 1074-82-4, name is Potassium 1,3-dioxoisoindolin-2-ide belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of Potassium 1,3-dioxoisoindolin-2-ide

A solution of 2 (1.0 g, 4.4 mmol), potassium phthalimide (0.4 g, 2.2 mmol) in DMF (10 mL) was stirred at 90 C for 10 h. The mixture was poured into H2O (30 mL) and the suspension was extracted with EtOAc (2 × 30 mL). The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure. Purification of the residue by flash chromatography (hexane:EtOAc, 20:1) gave 3 (0.41 g, 63%) as a white solid: mp 75-76.5 C; 1H NMR (300 MHz, CDCl3) delta 1.11 (s, 6H), 3.38 (s, 2H), 3.70 (s, 2H), 7.72-7.88 (m, 4H); 13C NMR (75 MHz, CDCl3) delta 24.6, 37.6, 44.5, 46.2, 123.3, 131.9, 134.1, 168.7; MS (ESI) m/z 318.0 [M+Na]+.

The synthetic route of 1074-82-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wu, Yong; Shi, Chen; Sun, Xiaowei; Wu, Xiaoming; Sun, Hongbin; Bioorganic and Medicinal Chemistry; vol. 19; 14; (2011); p. 4238 – 4249;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 3484-35-3, 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.

General procedure: A 50 mL round-bottom flask equipped with a reflux condenser and a magnetic stir bar was charged with indolin-2-one (10.0 mmol), ethanol(10 mL), acetone (7.3 mL, 0.1 mmol, 10.0 equiv), benzylamine(0.33 mL, 3.0 mmol, 0.3 equiv), and acetic acid (0.17 mL, 3.0 mmol,0.3 equiv). Then, the reaction mixture was heated under reflux for 2 h. The precipitation was filtered off and washed with cold PE (10 mL). The obtained product was dried for 30 min and used without further purification.

The chemical industry reduces the impact on the environment during synthesis 5-Methylindolin-2-one. I believe this compound will play a more active role in future production and life.

Reference:
Article; Hu, Wei-Qiang; Xu, Xiu-Hua; Qing, Feng-Ling; Journal of Fluorine Chemistry; vol. 208; (2018); p. 73 – 79;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 496-12-8, name is Isoindoline, 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 496-12-8, Recommanded Product: 496-12-8

General procedure: A literature procedure1 was modified by replacing triethylamine with N,N-diisopropylethylamine. To a stirred mixture of tetrahydroisoindoline (0.11 mL, 1.0 mmol), N-Boc-(R)-phenylalanine (265 mg, 1.0 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (182 mg, 1.0 mmol) and anhydrous 1-hydroxybenzotriazole (203 mg, 1.5 mmol) in N,N-dimethylformamide (3.0 mL) was added N,N-diisopropylethylamine (1.3 mL, 7.5 mmol). The mixture was stirred at 20 for 16 h. The solvent was evaporated and the residue was dissolved in ethyl acetate (20 mL) and the solution was washed with water (2 x 20 mL). The combined aqueous fractions were re-extracted with ethyl acetate (2 x 20 mL) and all the combined organic layers were washed with saturated aqueous sodium hydrogen carbonate (2 x 20 mL) then with brine (20 mL) filtered and dried (MgSO4). Column chromatography (25:75 ethyl acetate: dichloromethane) of the residue gave 7c (175 mg, 48%) as a cream solid,

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

Reference:
Article; Chan, A. W. Edith; Greenwood, Simon O. R.; Hansen, D. Flemming; Marson, Charles M.; Bioorganic and medicinal chemistry letters; (2020);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 552330-86-6, 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. 552330-86-6, name is 5-Bromoisoindolin-1-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A mixture of compound 5-bromoisoindolin-1-one(200 mg, 0.94 mmol, 1.0 eq), 1-methyl-3-(4,4,5,5-tetram-ethyl-i ,3,2-dioxaborolan-2-yl)- 1H-pyrazole (215 mg, 1.04mmol, 1.1 eq), cesium carbonate (922 mg, 2.83 mmol, 1.2eq), and Pd(dppf)C12 (21 mg, 0.03 mmol) in 1,4-dioxane(15mE) and water (2 mE) was stirred at 1000 C. for 16 hours under a nitrogen atmosphere. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (30%-100% EtOAc in PE) to give 4A (120 mg, 60% yield): ?H NMR (400 MHz, CDC13) oe 7.96 (s, 1H), 7.89 (d, J 0.8 Hz, 2H), 7.43 (d, J 2.2 Hz, 1H), 6.62 (d, J 2.3 Hz, 1H), 6.36 (s, 1H), 4.48 (s, 2H), 3.99 (s, 3H).

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-Bromoisoindolin-1-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Seal Rock Therapeutics, Inc.; BROWN, Samuel David; US2018/291002; (2018); A1;,
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. 7477-63-6, name is 7-Chloroisatin, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C8H4ClNO2

General procedure: To a well-stirred solution of isatin and malononitrile(1 mmol each) in ethanol (95percent, 4 mL) was added dimedone,4-hydroxycoumarin, 4-hydroxy-N-methylquinolin-2-one,or 2-methyl-pyrazol-2-one [generated in situ from ethylacetoacetate and hydrazine hydrate, 1 mmol each]. To thissolution was added THAM (30 mol percent) and stirring wascontinued at ambient temperature. Upon completion of thereaction (TLC), water (5 mL) was added and stirring wascontinued for 10 min more. Resultant solid product wasfiltered, washed repeatedly with water, and dried. The dried solid was washed thrice with hexaneechloroformmixture (1:1, v/v) and dried again. Resultant product didnot require any further purification.

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 7477-63-6.

Reference:
Article; Khot, Supriya S.; Anbhule, Prashant V.; Desai, Uday V.; Wadgaonkar, Prakash P.; Comptes Rendus Chimie; vol. 21; 9; (2018); p. 814 – 821;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 496-12-8,Some common heterocyclic compound, 496-12-8, name is Isoindoline, molecular formula is C8H9N, 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.

(5-bromo-2,4-dihydroxyphenyl)(isoindolin-2-yl)methanone, 7 (PA1): In a 50 mL, three-necked, round-bottomed flask, 5-bromo-2,4-dihydroxybenzoic acid (1.42 g, 5.65 mmol, 1.13 equivalent), l-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC, 1.02 g, 5.25 mmol, 1.05 equivalent) and 1-Hydroxybenzotriazole (HOBT, 776 mg, 5.75 mmol, 1.15 equivalent) were dissolved in dimethylformamide (10 mL) at room temperature. The mixture was stirred at the same temperature for 30 min before isoindoline (596 mg, 5 mmol, 1 equivalent) was added. After 18 h, the reaction mixture was diluted with ethyl acetate (50 mL) and washed sequentially with IN HC1 aqueous solution, saturated aqueous aHC03, and brine. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel; ethyl acetate: hexanes 1 :20 to 1 : 1) to yield PAl (1.17 g, 70% yield). XH NMR (500 MHz, DMSO-d6) delta 10.50 (s, 1H), 10.34 (s, 1H), 7.38-7.36 (m, 2H), 7.34 (s, 1H), 7.29-7.27 (m, 2H), 6.59 (s, 1H), 4.77 (s, 2H), 4.70 (s, 2H); 13C NMR (125 MHz, DMSO-d6) delta 166.6, 155.8, 154.7, 136.9, 131.7, 127.4, 122.9, 117.2, 103.7, 98.6, 52.7 (Rotamers were observed). LRMS (ESI) calculated for [M+H]+ 334.0, found 333.9.

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

Reference:
Patent; THE BOARD OF REGENTS OF THE UNIVERSITY OF TEXAS SYSTEM; CHUANG, David, T.; TSO, Shih-Chia; QI, Xiangbing; GUI, Wen-Jun; WU, Cheng-Yang; CHUANG, Jacinta, L.; TAMBAR, Uttam, K.; WYNN, R., Max; WO2015/89360; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

6941-75-9, name is 5-Bromoisoindoline-1,3-dione, 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. COA of Formula: C8H4BrNO2

5-bromo-2-ethylisoindoline-1,3-dioneTo a solution of 5-bromoisoindoline-1 ,3-dione (1 130 mg, 5 mmol) in THF (25 mL) was added iodoethane (0.606 mL, 7.50 mmol) and then slowly was added NaH (144 mg, 6.00 mmol). The resulting reaction was stirred at RT for 22 h. To the reaction mixture was added DMF (2 mL) then stirred at RT for 23 h. To the reaction mixture was added more DMF (3 mL) then was stirred at RT for 120 h. The reaction mixture was diluted with H20 (20 mL), acidified with HCI (1 mL, 1.0 N), extracted with EtOAc (3 x 20 mL), washed with brine (20 mL), dried over MgS04, filtered, evaporated down under vacuum, and purified by flash chromatography to afford desired product 5-bromo-2-ethylisoindoline-1 ,3-dione (899.7 mg, 3.54 mmol, 70.8 % yield). LC-MS mlz 254.1 (M+H)+, 0.90 min (ret. time).

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

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ASTEX THERAPEUTICS LIMITED; BOEHM, Jeffrey Charles; DAVIES, Thomas Glanmor; WOOLFORD, Alison Jo-anne; GRIFFITHS-JONES, Charlotte Mary; WILLEMS, Hendrika Maria Gerarda; NORTON, David; SAXTY, Gordon; HEIGHTMAN, Thomas Daniel; LI, Tindy; KERNS, Jeffrey K.; DAVIS, Roderick S.; YAN, Hongxing; WO2015/92713; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 35197-64-9, name is 2-Bromo-4-(1,3-dioxoisoindolin-2-yl)butanoic acid, 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 35197-64-9, Safety of 2-Bromo-4-(1,3-dioxoisoindolin-2-yl)butanoic acid

Step b: Preparation of tert-but 2-bromo-4-(l,3-dioxo-l,3-dihydro-2H-isoindol-2-yl) butanoate To a solution of compound obtained from Step a (180 mg, 0.576 mmoles) in tetrahydrofuran (5 mL) was added Boc anhydride (1 mL, 0.461 mmoles) and N,N- dimethylaminopyridine (7 mg, 0.057 mmoles). The reaction mixture was allowed to stir at room temperature for about 18 hours. After completion of reaction, solvent was azeotropically distilled using toluene and ethyl acetate to obtain a crude product. The crude product was purified on silica gel column using 20% ethyl acetate: hexane as eluent to get the desired product. Yield: 180 mg

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; RANBAXY LABORATORIES LIMITED; KHERA, Manoj Kumar; PALLE, Venkata P.; SATTIGERI, Viswajanani; SATTIGERI, Jitendra; SONI, Ajay; RAUF, Abdul Rehman Abdul; SIVAKUMAR, R.; REDDY, Ranadheer R.; MUSIB, Arpita; CLIFFE, Ian A.; BHATNAGAR, Pradip Kumar; RAY, Abhijit; SRIVASTAVA, Punit; DASTIDAR, Sunanda Ghosh; WO2012/38944; (2012); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 20780-72-7, 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. 20780-72-7, name is 4-Bromoisatin, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Isatin 1 (147.1 mg, 1 mmol), (E)-1-phenylpent-2-ene-1,4-dione (2a, 348.4 mg, 2 mmol), and thiourea I (57 mg, 0.1 mmol) were cooled to -20 °C, dissolved in toluene (3 mL), and the mixture was stirred at -20 °C for 24 h. The progress of the reaction was monitored by TLC and NMR spectroscopy. The product was isolated by direct column chromatography on silica gel (CH2Cl2/EtOAc 95:5 to 85:15)

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

Reference:
Article; Trubitson, Dmitri; ?ari, Sergei; Kaabel, Sandra; Kudrjashova, Marina; Kriis, Kadri; Jaerving, Ivar; Pehk, Tonis; Kanger, Tonis; Synthesis; vol. 50; 2; (2018); p. 314 – 322;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem