Month: May 2021

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

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

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

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 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

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

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

Application of 959235-95-1, The chemical industry reduces the impact on the environment during synthesis 959235-95-1, name is 6-(Trifluoromethoxy)indoline, I believe this compound will play a more active role in future production and life.

A mixture of 6-(trifluoromethoxy)indoline [CAS 959235-95-1] (577 mg, 2.84 mmol),2-(2-(4-(tert-butoxy)-4-oxobutoxy)-4-ch lorophenyl )-2-((3-methoxy-5-(methylsulfonyl)phenyl)amino)acetic acid 7d (1 .5 g, 2.84 mmol), HATU (1 .62 g, 4.26 mmol) and diisopropylethylamine (1 .4 mL, 8.5 mmol) in DMF (60 mL) was stirred at room temperature for 12 h. The mixture was diluted with water. The precipitate was filtered off and washed with water. The precipitate was taken upwith EtOAc, washed with an aqueous solution of K2003 10%, water, dried over MgSO4, filtered and the solvent was concentrated under reduced pressure. Purification was performed by flash chromatography on silica gel (15-40 pm, 120 g, heptane/EtOAc 60/40) to give, after crystallization from petroleum ether/diisopropyl ether, tert-butyl 4-(5-chloro-2-(1 -((3-methoxy-5-(methylsulfonyl)phenyl)amino)-2-oxo-2-(6-(trifluoromethoxy)indolin-1 -yl)ethyl)phenoxy)butanoate 9a (1 .02 g).

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-(Trifluoromethoxy)indoline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JANSSEN PHARMACEUTICALS, INC.; KATHOLIEKE UNIVERSITEIT LEUVEN; BARDIOT, Dorothee Alice Marie-Eve; KESTELEYN, Bart Rudolf Romanie; BONFANTI, Jean-Francois; RABOISSON, Pierre Jean-Marie Bernard; MARCHAND, Arnaud Didier M; (64 pag.)WO2018/178238; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference 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.

General procedure: A solution of chromones 1 (0.2 mmol), isatins 2 (0.3 mmol) and proline, or thioproline (0.5 mmol) in the 4.0 mL of EtOH at 80 C in oil bath for 3 h. After completion of the reaction, as indicated by TLC, the reaction solvent was directly removed, and purification by flash column chromatography (petroleum ether/EtOAc = 5:1~10:1) was carried out to furnish the corresponding products 3.

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

Reference:
Article; Yue, Jing; Chen, Shuang; Zuo, Xiong; Liu, Xiong-Li; Xu, Sheng-Wen; Zhou, Ying; Tetrahedron Letters; vol. 60; 2; (2019); p. 137 – 141;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 1074-82-4, These common heterocyclic compound, 1074-82-4, name is Potassium 1,3-dioxoisoindolin-2-ide, 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: A mixture of phthalimide10(6.8 mmol) dissolved in EtOH (20 mL) was gently boiled for about 1h. The hot solution was decanted from any solid into 1.25 mL of a specially prepared solution of KOH (15.25 g KOH dissolved in 15 mL of H2O and 45 mL of EtOH). A precipitate of potassium phthalimide separates at once. The mixture was stirred and cooled quickly to room temperature, and the precipitate was filtered under vacuum. To the alcoholic mother liquors a second 1 g portion of phthalimide was added, and the entire process was repeated. The two crops of crystals were united and washed with acetone to remove any unchanged phthalimide. After air-dried pure potassium phthalimidewas obtained as white crystals (yield 30%). In a second step, a mixture of potassium phthalimide (2.2 mmol),the appropriate dibromoalkane derivative (2.9 mmol) and 2.5 mL of acetone was stirred and refluxed for 24h, and then cooled to 15 C. After filtering off the precipitated potassium bromide, the cake was washed with acetone and the solvent evaporated to give pure compound.

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

Reference:
Article; Capela, Rita; Magalhaes, Joana; Miranda, Daniela; Machado, Marta; Sanches-Vaz, Margarida; Albuquerque, Ines S.; Sharma, Moni; Gut, Jiri; Rosenthal, Philip J.; Frade, Raquel; Perry, Maria J.; Moreira, Rui; Prudencio, Miguel; Lopes, Francisca; European Journal of Medicinal Chemistry; vol. 149; (2018); p. 69 – 78;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem