Tag: M.W=200-300

Electric Literature of 5394-18-3, 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. 5394-18-3, name is 2-(4-Bromobutyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a suspension of the corresponding secondary amine (3.22 mmol) and anhydrous K2CO3 (765 mg, 5.48 mmol) in CH3CN (20 mL) was added the intermediates 3-5 (0.60 mmol). The mixture was refluxed for 6-8 h. The solvent was removed under reduced pressure. The residue was diluted with water (30 mL) and the mixture was extracted with dichloromethane (30 mL¡Á3). The combined organic phases were washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified on a silica gel chromatography in petroleum ether/acetone (20/1, v/v) to afford compound 7-9

The chemical industry reduces the impact on the environment during synthesis 2-(4-Bromobutyl)isoindoline-1,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Article; Song, Qing; Li, Yan; Cao, Zhongcheng; Qiang, Xiaoming; Tan, Zhenghuai; Deng, Yong; Bioorganic Chemistry; vol. 84; (2019); p. 137 – 149;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 6941-75-9,Some common heterocyclic compound, 6941-75-9, name is 5-Bromoisoindoline-1,3-dione, molecular formula is C8H4BrNO2, 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 suspension of 5-bromo-1 H-isoindole-1 ,3(2H)-dione (ABCR, 5.Og) and triphenylphosphine (8.7Og) in tetrahydrofuran (THF) (10OmL) under nitrogen at room temperature was added di-t-butyl azodicarboxylate (7.64g). The suspension was cooled in an ice/water bath and to this was added iso-propanol (2.032 ml_). The reaction mixture was allowed to warm to room temperature to give a pale yellow solution. After 60 minutes, the solvent was removed in vacuo and the residue was dissolved in DCM (3OmL). This was applied to a 75Og silica cartridge and eluted with a gradient of 0-40% ethyl acetate in cyclohexane over 8CV. The required fractions were combined and evaporated in vacuo to give the title compound (5.27g) as a pale yellow solid.1H NMR (CDCI3): 7.95 (1 H, d, J=1.5Hz), 7.84 (1 H, dd, J=1.5, 8Hz), 7.68 (1 H, d, J=8Hz), 4.53 (1 H, heptet, J=7Hz), 1.49 (6H, d, J=7Hz)

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

Reference:
Patent; GLAXO GROUP LIMITED; JIN, Qi; WO2010/102968; (2010); 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. 959235-95-1, name is 6-(Trifluoromethoxy)indoline, This compound has unique chemical properties. The synthetic route is as follows., Safety of 6-(Trifluoromethoxy)indoline

HATU (1 .54 g, 4.06 mmol) was added to a mixture of 6-(trifluoromethoxy)indoline [CAS 953906-76-8] (550 mg, 2.70 mmol), 2-(4-chloro-2-fluorophenyl)-2-((3- (2-hydroxyethoxy)-5-methoxyphenyl)amino)acetic acid 2e (1 g, 2.70 mmol) and diisopropylethylannine (1 .34 mL, 8.1 1 mmol) in DMF (30 mL). The resulting mixture was stirred at room temperature for 12 h. The mixture was diluted with water. The precipitate was filtered off, and washed with water. The solid was dissolved in EtOAc, washed with a 10% solution of K2CO3 in water and then with brine. The organic layer was dried over MgSO4, filtered, and the solvent was evaporated under reduced pressure. The crude residue was purified by flash chromatography on silica gel (15-40 muetaeta, 80 g, CH2CI2/MeOH 99.5/0.5) to afford 2-(4-chloro-2-fluorophenyl)-2-((3-(2-hydroxyethoxy)-5-methoxyphenyl)amino)-1 -(6-(trifluoro- methoxy)indolin-1 -yl)ethanone (Compound 6, 500 mg). An analytical sample of Compound 6 was obtained by crystallized from diisopropyl ether. Compound 6: 1H NMR (500 MHz, DMSO-cfe) delta ppm 3.14 – 3.22 (m, 2 H) 3.58 – 3.68 (m, 5 H) 3.80 – 3.90 (m, 2 H) 4.05 – 4.15 (m, 1 H) 4.38 – 4.47 (m, 1 H) 4.80 (t, J=5.5 Hz, 1 H) 5.70 (d, J=9.1 Hz, 1 H) 5.79 (t, J=1 .9 Hz, 1 H) 5.93 (d, J=1 .9 Hz, 2 H) 6.63 (d, J=9.1 Hz, 1 H) 7.03 (dd, J=8.2, 1 .6 Hz, 1 H) 7.31 – 7.37 (m, 2 H) 7.42 – 7.51 (m, 2 H) 8.02 (s, 1 H) LC/MS (method LC-A): Rt 3.39 min, MH+ 555 Melting point: 166C

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 959235-95-1.

Reference:
Patent; JANSSEN PHARMACEUTICALS, INC.; KATHOLIEKE UNIVERSITEIT LEUVEN; BARDIOT, Dorothee Alice Marie-Eve; BONFANTI, Jean-Francois; KESTELEYN, Bart Rudolf Romanie; MARCHAND, Arnaud Didier M; RABOISSON, Pierre Jean-Marie Bernard; (76 pag.)WO2017/167953; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 5332-26-3, These common heterocyclic compound, 5332-26-3, name is 2-(Bromomethyl)isoindoline-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.

General procedure: Benzimidazole (1 mmol) and potassium hydroxide (1 mmol) were dissolved in ethyl alcohol (60 mL). The alkyl halide (1 mmol) was slowly added after the obtained reaction mixture was stirred at room temperature for 1 h. The solution was refluxed for 6 h, cooled to roomtemperature and the precipitated potassium chloride was removed by filtration. The solvent was removed by distillation. The product was then crystallized, washed several times with diethyl ether and then dried in vacuo. To a solution of 1-alkylbenzimidazole (1 mmol) in dried DMF (4 mL), alkyl halide (1 mmol) was added slowly and the reaction mixture was stirred at 80 C for 24 h under argon. After completion of the reaction, the DMF was removed by vacuum and diethyl ether (15 mL) was added to the mixture. The solid was washed with diethyl ether (2 ¡Á 15 mL) and dried under vacuum. The product was crystallized in an ethanol/diethyl ether mixture (3:1) at room temperature. The purified compounds were obtained as white or cream solids. Their structures were characterized by NMR (1H and 13C), FTIR, ESI-FTICR-MS (for 2 and 4) spectroscopic methods and elemental analysis

The synthetic route of 5332-26-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Akkoc, Senem; Goek, Yetkin; Ilhan, Ilhan Oezer; Kayser, Veysel; Beilstein Journal of Organic Chemistry; vol. 12; (2016); p. 81 – 88;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 3783-77-5, 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. 3783-77-5, name is 2-(3-Oxobutyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

2-(4-bromo-3-oxobutyl)isoindoline-1,3-dione To a solution of 2-(3-oxobutyl) isoindole-1 ,3-dione (3.0 g, 13.81 mmol) in methanol (100 imL) was added bromine (2.43 g, 15.19 mmol) dropwise at 0C. The reaction mixture was stirred at the same temperature for 30 min and then at room temperature for 15 h. To the resulting clear solution was added concentrated sulfuric acid (10 M, 20 mL) and the resulting mixture was stirred at room temperature for 24 h. The precipitated solid was filtered and air- dried, afforded the desired product, 2-(4-bromo-3-oxobutyl)isoindoline-1 ,3- dione, as a white solid, (1 .85 g, 46% yield).

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-(3-Oxobutyl)isoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MONASH UNIVERSITY; THE UNIVERSITY OF WESTERN AUSTRALIA; BAELL, Jonathan; PIGGOTT, Matthew; RUSSELL, Stephanie; TOYNTON, Arthur; RAHMANI, Raphael; FERRINS, Lori; NGUYEN, Nghi; (178 pag.)WO2015/172196; (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. 552330-86-6, name is 5-Bromoisoindolin-1-one, A new synthetic method of this compound is introduced below., SDS of cas: 552330-86-6

To a 25 mL rmmd-boitom t1ask was added 5-bromo-2,3-dihydro-H-1-isoindol-1-one10 135a (500 mg, 2.36 mmol, 1.0 equiv.), di-tert-butyl dicarbonate (800 mg, 3.67 mmol, 1.5equiv.), 4-dimethylaminopyridine (30 mg, 0.25 mmol, 0.1 equiv.), and tetrahydrofuran (5mL). The resulting mixture v.¡¤as stirred at room temperatme overnight. The mixture wa.-.:diluted with 500 mL of brine and extracted with ethyl acetate (250 mL x 3). The organicextracts Vere combined, dried over anhydrous sodium sulfate, and concentrated under15 vacuum. The residue was pmified by Fla.-.:h-Prep-HPLC using the following conditions(IntelFlash-l): Column, silica gel: mobile phase: EA: PE”‘O: 100 increasing toEA: PE”’20:80within 25 min; Detector, UV 2.54 nm. Removal of solvents gave tert-butyl 5-bromo-1-oxo-2,3-dihydro-lH-isoindole-2-carboxylate l35b ( 6.59 mg, 90%) as a light yellow solid.

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; ARDELYX, INC.; CHAO, Jianhua; JAIN, Rakesh; HU, Lily; LEWIS, Jason Gustaf; BARIBAULT, Helene; CALDWELL, Jeremy; (582 pag.)WO2018/39386; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 6941-75-9, name is 5-Bromoisoindoline-1,3-dione, molecular formula is C8H4BrNO2, 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. Safety of 5-Bromoisoindoline-1,3-dione

4-bromo phthalimide (manufactured by Tokyo Kasei Kogyo) 9.95 g (44.0 mmol) were placed in a two-necked eggplant flask 50ml was replaced with nitrogen gas.Then added iodine 5.87g (23.1mmol) and 10% fuming sulfuric acid (Yotsuhata Chemical Industry Co., Ltd.) 12ml, it was subjected to 23 hours of reaction at 90C .The reaction mixture was poured into ice cooled to room temperature, filtered through a glass filter, to give a yellow solid 12.8 g. The resulting solid was dissolved in concentrated sulfuric acid 35 ml, the reaction was carried out for 5 hours at 130C..The reaction mixture was ice-cooled, and filtered the solid precipitated by adding ice water to give a solid 13.8g of phthalic acid derivatives. Next, the resulting solid was dissolved at room temperature sodium hydroxide 3.6g aqueous solution dissolved in water 18 ml. The basic aqueous solution of acetic acid was added to adjust the pH to 3-4, filtered the white precipitate of the mono sodium salt of the phthalic acid derivative precipitated. The resulting white solid was suspended in water, to pH 1 or less with concentrated hydrochloric acid to give a white solid 6.45g again as phthalic acid derivatives. The solid was dissolved in toluene 48 ml, was added acetic anhydride 8.7g (85.7mmol), the reaction was carried out for 4 hours at 105C. To give a white solid 5.87g The reaction mixture was concentrated under reduced pressure.The solid was purified by recrystallization in toluene to give 4-bromo-5-iodo-phthalic anhydride object 5.13g of (14.5mmol) (33% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6941-75-9, its application will become more common.

Reference:
Patent; Tosoh Corporation; Watanabe, Masato; Ohashi, Tomokazu; Fujita, Takumi; (137 pag.)JP5716821; (2015); B2;,
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 675109-26-9 as follows. Recommanded Product: 675109-26-9

A stirred solution of 6-bromo-2,3-dihydro-1 H-isoindol-1 -one (3.4 g, 14.16 mmol) and 2-chloro-1- (1 ,2,3,4-tetrahydroisoquinolin-2-yl)ethan-1-one (3.6 g, 17.00 mmol) in DMF (47 mL) was cooled in an ice bath under nitrogen before adding NaH (0.70 g, 17.00 mmol) in portions. The reaction was allowed to warm to room temperature over an hour and was then quenched with NH4CI (sat., aq.). The pH was adjusted to pH 7 with citric acid (5%, aq.) and the product was extracted with IPAiCHCh (1 :3, x3). The combined organic layers were washed brine, dried over MgS04, filtered and concentrated under vacuum to yield 6-bromo-2-[2-oxo-2-(1 ,2,3,4- tetrahydroisoquinolin-2-yl)ethyl]-2,3-dihydro-1 H-isoindol-1 -one as a brown solid which was used crude. MS: [M+H]+ = 385.

According to the analysis of related databases, 675109-26-9, the application of this compound in the production field has become more and more popular.

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

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. 959235-95-1, name is 6-(Trifluoromethoxy)indoline, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C9H8F3NO

A mixture of 6-(trifluoromethoxy)indoline [CAS 959235-95-1] (2 g, 9.84 mmol), 2-(4-chlorophenyl)acetic acid [CAS 1878-66-6] (1.85 g, 10.8 mmol), HATU (5.6 g, 14.8 mmol) and diisopropylethylamine (4.9 ml_, 29.5 mmol) in DMF (40 ml_) was stirred at room temperature for 12 h. Water was added and the precipitate was filtered off. The residue was taken up with EtOAc. The organic solution was washed with a 10% aqueous solution of K2CO3, brine, dried over MgSO4, filtered and the solvent was evaporated under reduced pressure. The residue was purified by chromatography on silica gel (15-40 muiotatauiota, 80 g, heptane/EtOAc gradient 90/10 to 60/40). The pure fractions were combined and the solvent was concentrated under reduced pressure to give 2-(4-chlorophenyl)-1 -(6-(trifluoromethoxy)indolin-1 – yl)ethanone 7a (3 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; BONFANTI, Jean-Francois; KESTELEYN, Bart, Rudolf, Romanie; BARDIOT, Dorothee, Alice, Marie-Eve; MARCHAND, Arnaud, Didier, M; COESEMANS, Erwin; DE BOECK, Benoit, Christian, Albert, Ghislain; RABOISSON, Pierre, Jean-Marie, Bernard; (79 pag.)WO2018/215316; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 118289-55-7,Some common heterocyclic compound, 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-one, molecular formula is C10H9Cl2NO, 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.

3. Preparation of ZPR in water/Na3CO . Na2SO4. In a three necked flask was charged BITP HC1 (lOg), CEI (10.35g) Na2C03 (14.1 g, ), Na2SO4 (40g) and water (50. 7g) and the reaction mixture was heated at reflux for 9 hours. After 9 hours reflux, the ziprasidone peak is No.71% area from the reaction mixture.; 6. Preparation of ZPR in the presence of Na2SO4. In a 250g three necked flask was charged water (25ml), Na2C03 (6.91g), Na2S04 (19.72g), BITP HCl (4.9g) and CEI (4.68g). The mixture was stirred at-100C for 12 hours. The isolated solid weights after drying 7.77g (purity by HPLC 85.15%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Chloro-5-(2-chloroethyl)indolin-2-one, its application will become more common.

Reference:
Patent; TEVA PHARMACEUTICAL INDUSTRIES LTD.; TEVA PHARMACEUTICALS USA, INC.; WO2005/40160; (2005); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem