Indolines-derivatives

Adding a certain compound to certain chemical reactions, such as: 132898-96-5, name is 2,3-Dioxoindoline-5-sulfonyl chloride, 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 132898-96-5, name: 2,3-Dioxoindoline-5-sulfonyl chloride

General procedure: A stirred solution of N-Boc protected pyrrolidine (1.00 mmol) in dry DCM (2.2 mL) at 0 C under argon atmosphere was treated dropwise with TFA (10.00 mmol). Stirring was continued at 0 C for 30 min and at ambient temperature for 2 h. Subsequently, the solution was poured to ice-cooled 10% aq NaOH (15 mL) and extracted with DCM (3 × 15 mL). The combined organic phase was dried over MgSO4 and concentrated in vacuo to obtain a colorless oil as the corresponding unprotected pyrrolidine. After that a solution of the free pyrrolidine and DIPEA (2.00 mmol) in CHCl3 (1.1 mL) was added dropwise to a stirred solution of 5-chlorosulfonyl isatin (1.50 mmol) in CHCl3/THF (1:1, 19 mL) at room temperature. The resulting solution was stirred at room temperature for 1 h and the solvent was completely removed in vacuo. The crude product was purified by flash column chromatography to obtain the corresponding inhibitors.

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-Dioxoindoline-5-sulfonyl chloride, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Limpachayaporn, Panupun; Schaefers, Michael; Schober, Otmar; Kopka, Klaus; Haufe, Guenter; Bioorganic and Medicinal Chemistry; vol. 21; 7; (2013); p. 2025 – 2036;,
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. 912999-79-2, name is 5-Chloroisoindoline hydrochloride, A new synthetic method of this compound is introduced below., Computed Properties of C8H9Cl2N

A mixture of 2-chloro-N-(1 H-indazol-5-yl)-5 ,7-dihydro furo[3 ,4-d]pyrimidin- 4-amine (1.0 g ), ZiniI.8 g, 7.8 mmcl) and 5-chloroisoindoline hydrochloride (0.58 g, 2.6 mmol) in NMP (20 mL) was heated at 150 °C lbr 1 h. The reaction mixture was cooled to room temperature, filtrated and purified by HPLC to give the title compound (110 mg, 9.12percent). ?HNMR(400 MHz, DMSO-d6)oe 12.95(1 H, s), 8.83(1 H, s), 8.26 (1 H, s), 8.08 (1 H, s), 7.62 (1 H, d, J=8.80 Hz), 7.49 (1 H, d, J8.80 Hz), 7.34 (1 H, d, J7.60 Hz), 4.86-4.71 (8 H, m). MS (ES+) rn/e 405 (M+H).

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; KADMON CORPORATION, LLC; KIM, Ji-in; LIU, Kevin; POYUROVSKY, Masha; LU, Dan; ZHU, Zhenping; WO2015/54317; (2015); A1;,
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Indoline | C8H9N – PubChem

Related Products of 17702-83-9, These common heterocyclic compound, 17702-83-9, name is 2-(8-Bromooctyl)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: 0.91 g (3.6 mmol) N-(2 -bromoethyl) phthalimide was dissolved 20 mL DMF, added 0.53 g (3 mmol)1-benzylpiperazine, 0.62 g (4.5 mmol) K2CO3, heated to 60-70 °C reacted for 4 h, TLC detection, until the benzylpiperazinewas complete reaction. 30 mL of water was added, extracted three times withethyl acetate (20 mL× 3), the organic layer was extracted four times (30mL × 4)with saturated brine, dried with anhydrous magnesium sulfate, and the solventwas distilled off under reduced pressure, cooled to room temperature, silicagel column chromatography (100-200 mesh silica gel, eluent petroleum ether:ethyl acetate = 1:1 – 1: 4) to give 0.7 g (67percent yield) as a white solid. #10;

The synthetic route of 17702-83-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Si, Weijie; Zhang, Tao; Zhang, Lanxiang; Mei, Xiangdong; Dong, Mengya; Zhang, Kaixin; Ning, Jun; Bioorganic and Medicinal Chemistry Letters; vol. 26; 9; (2016); p. 2380 – 2382;,
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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. 19155-24-9, name is 3,3-Dimethylindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C10H11NO

5-bromo-1,3-dihydro-3,3-dimethyl-2H-indol-2-one 3,3-dimethyl-indol-2-one (0.65 g, 4.03 mmnol) and sodium acetate (0.33 g, 4.07 mmol) were stirred in acetic acid (5 cm3) then bromine (0.66 g, 4.13 mmol) in acetic acid (5 cm3) was added drop-wise to the reaction mnixture. The reaction was stirred for 50 min., and then poured into water. The mixture was basified with sodium carbonate and then extracted with ethyl acetate (*3), dried (MgSO4), filtered, and evaporated to the title compound (0.89 g, 92percent) 1H NMR (DMSO-d6) delta 1.21 (s, 6H), 6.76 (d, 1H, J=8.22 Hz), 7.29 (dd, 1H, J=2.12 Hz, 8.23 Hz), 7.49 (d, 1H, J=2.03 Hz), 10.4 (s, 1H).

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 19155-24-9.

Reference:
Patent; Wyeth; Ligand Pharmaceuticals, Inc.; US6462032; (2002); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 825-70-7, name is 5-Fluoro-2-methylindoline, molecular formula is C9H10FN, 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. COA of Formula: C9H10FN

Under argon atmosphere conditions, add 0.0151g (0.10mmol) of 5-fluoro-2-methylindolinoline (1d), 0.0013g (0.002mmol) of acid eosinY, 0.150g of Antarctic lipase CAL- A, 0.0146 g (0.10 mmol) of n-octyl mercaptan, 0.104 g (0.50 mmol) of allyl-3-methoxyphenyl carbonate (2b), methyl tert-butyl ether (TBME) 2.0 mL;The reaction was stirred at 45 C for 6 hours under a 6w white light. After the reaction, the insoluble enzyme was removed by suction filtration, the solvent was distilled off under reduced pressure, and the solvent was separated by column chromatography. The eluent: (V) petroleum ether / (V) Ethyl acetate = 30/1. 0.0190 g of a yellow liquid product (3db) was obtained with a product yield of 81%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 825-70-7, its application will become more common.

Reference:
Patent; Central China Normal University; Zhou Shaolin; Shi Weimin; (16 pag.)CN110437123; (2019); A;,
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Indoline | C8H9N – PubChem

These common heterocyclic compound, 20780-72-7, name is 4-Bromoisatin, 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. Computed Properties of C8H4BrNO2

4-bromoisatin 1.0g (4.4mmol), methyl acrylate 0.46g (5.3mmol), PdCl2(PPh3)2 0.15g (0.22mmol), K3PO4 1.6g (6.2mmol). Place into microwave reaction flask. Add 5 ml DMF. Place under argon protection. In the microwave reactor 145 °C reaction 30min. TLC detection after the reaction is complete, the reaction solution with 100 ml saturated salt water washing 3 times, dichloromethane is used for extraction, the combined organic phase, anhydrous sodium sulfate drying, developing agent for petroleum ether: ethyl acetate=5:1 – 1: 1,200 – 300 mesh silica gel column chromatography purification, be 4 – acrylic acid methyl ester indole dione 0.65g, yield 64percent.

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

Reference:
Patent; Tianjin Kunjian Bio-pharmaceutical Co., Ltd.; Yu Peng; Han Kailin; Mao Huihua; Qiu Dongxu; (8 pag.)CN104387312; (2017); B;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 18711-13-2,Some common heterocyclic compound, 18711-13-2, name is 4,7-Dichloroindoline-2,3-dione, molecular formula is C8H3Cl2NO2, 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 solution of 4,7-dichloroisatin (0.68 mmol, 1.0 eq) in DMF (4 mL) was added K2CO3 (0.68 mmol, 1.0 eq) at room temperature, the mixture was stirred for about 30 min, and then the propargyl bromide (0.75 mmol, 1.1 eq) was added dropwise. The mixture was stirred overnight at room temperature. Upon completion, EtOAc and H2O were added. The aqueous layer was extracted with EtOAc for several times; the combined organic layers were washed with H2O for several times to remove the DMF, and then washed with brine, dried over MgSO4 and evaporated to give the products. Compound 2, saffron solid, yield: 76%, m. p.: 151.8-153.3 C, Rf = 0.52 (petroleum ether/ethyl acetate 2/1). 1H NMR (400 MHz, CDCl3) delta 7.51 (d, J = 8.7 Hz, 1H), 7.10 (d, J = 8.7 Hz, 1H), 4.94 (d, J = 2.4 Hz, 2H), 2.34 (t, J = 2.4 Hz, 1H); 13C NMR (100 MHz, CDCl3) delta 178.68, 157.00, 146.19, 140.48, 133.05, 126.79, 117.16, 116.11, 77.22, 73.27, 31.94.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4,7-Dichloroindoline-2,3-dione, its application will become more common.

Reference:
Article; Yu, Bin; Wang, Sai-Qi; Qi, Ping-Ping; Yang, Dong-Xiao; Tang, Kai; Liu, Hong-Min; European Journal of Medicinal Chemistry; vol. 124; (2016); p. 350 – 360;,
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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

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