Category: indolines-derivatives

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

A mixture of 4-bromophthalic anhydride (25 g) in formamide (75 ml) was heated at 2000C for 16 hours then allowed to cool to room temperature. The reaction mixture was diluted with water (200 ml), filtered, the filter cake was washed with water then diethyl ether and sucked dry to give 20.85 g of light mustard solid.280 ml of 1 M Borane-THF complex was added dropwise to a stirred solution of 4-bromophthalimide (20.85 g; 92.2 mmol) in anhydrous THF (200 ml) at O0C then heated at reflux overnight. The reaction was cooled to O0C then treated cautiously with methanol (100 ml) followed by 2M HCI (100 ml) then heated at reflux for 3 hours. The reaction mixture was cooled and the organics evaporated. The aqueous was diluted with water (100 ml) the extracted with DCM (x3). The aqueous was basified with 2M NaOH then extracted with DCM (x3). The combined DCM extracts were dried (MgSO4), filtered and evaporated to give 6.99 g of 5-bromo-2,3-dihydro-1H-isoindole as a dark brown gummy solid. 1H NMR (DMSO-d6) 7.45 (1H, s), 7.36 (1 H1 d), 7.20 (1H, d), 4.05 (4H, s).

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

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; WO2008/44054; (2008); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 17564-64-6, The chemical industry reduces the impact on the environment during synthesis 17564-64-6, name is 2-(Chloromethyl)isoindoline-1,3-dione, I believe this compound will play a more active role in future production and life.

General procedure: The initial carbonyl compound (50 mmol) was dissolved/suspended in ethanol (50 mL) and magnetically stirred with thiosemicarbazide (50 mmol) and catalytic amounts of acetic acid for 8-24 h at room temperature. The obtained thiosemicarbazone was filtered, washed with appropriate solvent (n-hexane, petroleumether or diethyl ether) and dried under vacuum. The intermediate thiosemicarbazone (50 mmol) reacted with ethyl bromoacetate (50 mmol), in methanol (50 mL) and sodium acetate (50 mmol) at room temperature under magnetic stirring for 24 h. The resulting 4-thiazolidinone was poured on ice, filtered or extracted with chloroform (3 x 100 mL) and purified by column chromatography (SiO2, ethyl acetate/n-hexane). Then, the obtained thiazolidinone (50 mmol) was dissolved/suspended in 50 mL of anhydrous acetone in the presence of anhydrous potassium carbonate (50 mmol), and reacted with equimolar amounts of 4-nitrobenzyl bromide, 1-(chloromethyl)naphthalene and N-(chloromethyl)phthalimide for 24-48 h. The product was poured on ice, filtered or extracted with chloroform (3 x 50 mL) and purified by column chromatography (SiO2, ethyl acetate/n-hexane) in order to obtain the title compoundsin high yields. 7.1.58 2-((2-(2-(4-Methylpentan-2-ylidene)hydrazono)-4-oxothiazolidin-3-yl)methyl)isoindoline-1,3-dione (6C) Yellow powder, mp 66-67 C, 75% yield; 1H NMR (400 MHz, DMSO-d6): delta 0.91-0.92 (d, J = 6.8 Hz, 6H, 2 * CH3), 1.91 (s, 3H, CH3), 1.94-2.01 (m, 1H, CH), 2.14-2.16 (d, J = 7.2 Hz, 2H, CH2), 3.82 (s, 2H, CH2, thiazolidinone), 5.73 (s, 2H, ArCH2), 7.74-7.80 (m, 2H, Ar), 7.86-7.88 (m, 2H, Ar).

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

Reference:
Article; De Monte, Celeste; Carradori, Simone; Bizzarri, Bruna; Bolasco, Adriana; Caprara, Federica; Mollica, Adriano; Rivanera, Daniela; Mari, Emanuela; Zicari, Alessandra; Akdemir, Atilla; Secci, Daniela; European Journal of Medicinal Chemistry; vol. 107; (2016); p. 82 – 96;,
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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. 400727-63-1, name is tert-Butyl 5-nitroisoindoline-2-carboxylate belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Product Details of 400727-63-1

To 560mg of P13 in 20 mL of ethanol was added 56 mg of 10% Pd/C and the mixture shaken under 35 psi of hydrogen gas for 15 minutes. The mixture was filtered and evaporated to dryness yielding 516 mg of P14.

The synthetic route of 400727-63-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; CHELLIAH, Mariappan, V.; CHACKALAMANNIL, Samuel; GREENLEE, William, J.; EAGEN, Keith, A.; GUO, Zhuyan; CLASBY, Martin, C.; XIA, Yan; JAYNE, Charles, L.; DWYER, Michael; KEERTIKAR, Kartik, M.; CHAN, Tin-Yau; WANG, Li; WO2011/17296; (2011); A1;,
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Related Products of 1677-48-1, The chemical industry reduces the impact on the environment during synthesis 1677-48-1, name is 5,6-Dichloroindoline-2,3-dione, I believe this compound will play a more active role in future production and life.

A 250 mL round bottom flask was charged with 5,6-dichloroisatin(5,6-dichloroisatin) (500 mg, 2.32 mmol)was dissolved in methanol (MeOH) (92.80 ml), and then, Indoxyl acetate (405.48 mg, 2.315 mmol) Sodium carbonate (Na2CO3) (637.83 mg, 6.02 mmol) was added thereto, followed by stirring at 65 DEG C for 12 hours. The reaction is terminated using TLC (Rf = 0.4, ethyl acetate / hexane = 1/2 (v / v)) and the product is allowed to cool down on ice until a lump of crystals is formed. After the crystals are formed, the solvent is removed by filtration, the filtrate is discarded, and the product is washed several times with a solvent (ethanol / water = 1/1 (v / v)). The product was filtered and dried in a vacuum pump and used in the next step without further purification.

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, 5,6-Dichloroindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CK BIOTECH; C Kei Bio Tech Co., Ltd.; CHOI KANG YELL; Choi Gang-yeol; HAN GYOON HEE; Han Gyun-hui; LEE CHUL HO; Lee Cheol-ho; SEO SEOL HWA; Seo Seol-hwa; (31 pag.)KR2018/119941; (2018); A;,
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Indoline | C8H9N – PubChem

Electric Literature of 5394-18-3,Some common heterocyclic compound, 5394-18-3, name is 2-(4-Bromobutyl)isoindoline-1,3-dione, molecular formula is C12H12BrNO2, 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.

2-[4-(4-Morpholinyl)butyl]-1H-isoindole-1,3(2W)-dione (307). A mixture of 4- bromobutylphthalimide (10.0 g, 35.4 mmol), K2CO3 (5.88 g, 42.5 mmol) and morpholine (4.6 mL, 53.1 mmol) in DMF (100 mL) was stirred at 100 0C for 8 h, cooled to 20 0C and the solvent evaporated. The residue was partitioned between EtOAc (300 mL) and water (300 mL), the organic fraction washed with water (2 x 50 mL) and brine (50 mL), dried and the solvent evaporated. The residue was purified by chromatography, eluting with EtOAc, to give phthalimide 307 (9.59 g, 94%) as a clear oil: 1H NMR delta 7.81-7.86 (m, 2 H, Harom), EPO 7.68-7.73 (m, 2 H1 Haram), 3.66-3.72 (m, 6 H, 2 x CH2O, CH2N), 2.41 (br t, J = 4.5 Hz, 4 H, 2 x CH2N), 2.35 (br dd, J = 7.6, 7.4 Hz, 2 H, CH2N), 1.69-1.76 (m, 2 H, CH2), 1.50-1.58 (m, 2 H, CH2).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(4-Bromobutyl)isoindoline-1,3-dione, its application will become more common.

Reference:
Patent; AUCKLAND UNISERVICES LIMITED; WO2006/104406; (2006); 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 132898-96-5 as follows. Application In Synthesis of 2,3-Dioxoindoline-5-sulfonyl chloride

General procedure: To a stirred solution of the N-Boc-protected pyrrolidine (1.0 mmol) in dry DCM (3 mL) at 0 C under argon atmosphere, TFA (1.14 g, 10.0 mmol) was added dropwise. The obtained solution was stirred at 0 C for 30 min followed by stirring at r.t. for 2 h. Subsequently, the solution was poured to cold 10% aq. NaOH (15 mL) and extracted with DCM (3 ¡Á 15 mL). The combined organic phases were dried over MgSO4 and concentrated under reduced pressure resulting in the corresponding unprotected pyrrolidine, which was used in the next step without further purification. The free pyrrolidine (ca. 1 mmol) from the previous step was then taken up in CHCl3 (2.2 mL) and DIPEA (2.0 mmol) was added. The solution was added dropwise to a stirred solution of 5-chlorosulfonyl isatin (1.5 mmol) in CHCl3/THF (1:1, 15 mL) at room temperature. The resulting mixture was stirred further for 1 h and the solvent was removed under reduced pressure. After purification by flash column chromatography the target isatin sulfonamide was obtained.

According to the analysis of related databases, 132898-96-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Limpachayaporn, Panupun; Riemann, Burkhard; Kopka, Klaus; Schober, Otmar; Schaefers, Michael; Haufe, Guenter; European Journal of Medicinal Chemistry; vol. 64; (2013); p. 562 – 578;,
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Indoline | C8H9N – PubChem

Electric Literature of 5332-26-3, 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. 5332-26-3 name is 2-(Bromomethyl)isoindoline-1,3-dione, 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: The vacuum dried intermediate 3 (0.002 mol) was then reacted with mono- and di-substituted benzoic acids (0.003 mol) separately in presence of anhydrous potassium carbonate (0.003 mol) in DMF (10 mL). The reaction mixture was stirred at room temperature for about 2 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was poured into ice-cold water and allowed stir for 10 min. The solid obtained was filtered and washed successively with distilled water and recrystallized from ethanol to obtain4(a-n).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(Bromomethyl)isoindoline-1,3-dione, and friends who are interested can also refer to it.

Reference:
Article; Kumar, C.S. Chidan; Loh, Wan-Sin; Chandraju, Siddegowda; Win, Yip-Foo; Tan, Weng Kang; Quah, Ching Kheng; Fun, Hoong-Kun; PLoS ONE; vol. 10; 3; (2015);,
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Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 56341-37-8, name is 6-Chlorooxindole, 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 56341-37-8, COA of Formula: C8H6ClNO

6-Chloroindolin-2-one (8.35 g, 50 mmol) and 3-chloro-2-fluorobenzaldehyde (8.295 g, 52.5 mmol) were stirred at reflux in the presence of piperidine (1 ml) for 6 hours. The reaction suspension was then filtered, and the solid obtained was washed with methanol and dried to give a yellow solid product, (E)-6-chloro-3-(3-chloro-2-fluorobenzylidene)indol2-one (14.63g, 47.5mmol). Yield: 95%. 1H NMR (400MHz, DMSO): delta 10.85 (s, 1 H), 7.70 (q, J=7.3Hz 2 H), 7.54 (s, 1 H), 7.36 (t, J=8Hz 1 H), 7.16 (d, J=8Hz 1 H), 6.92-6.86 (m, 2 H); MS: Calcd for C15H9Cl2FNO ([M+H]+): 308, found: 308.0.

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; Xiao, Fei; MA, Jie; XIAO, Fei; REN, Hongjun; WANG, Wei; XU, Hongtao; WANG, Meng; ZOU, Lihui; DING, Fei; SU, Fei; (41 pag.)EP3498712; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 132898-96-5, 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. 132898-96-5 name is 2,3-Dioxoindoline-5-sulfonyl chloride, 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.

A mixture of dimethylamine (2M solution in THF) (0.668 mmol, 1.3 eq) and DIPEA (0.139 g, 1.02 mmol, 2 eq) was added to a solution of rpm 121 (0.126 g, 0.514 mmol) in anhydrous THF (4 ml) at 0 0C under Ar. The reaction mixture was stirred overnight at room temperature, and the mixture was poured into water (5 ml). The product was extracted with ethyl acetate (3 x 10 ml). The organic extracts were collected, dried over Na2SO4 and the solvent removed under reduced pressure. The pure compound rpm 123 was obtained after trituration with ethyl acetate (5 ml) as a yellow solid (0.90 g, 0.354 mmol, 68%), mp 150- 152 0C (lit mp 233 0C.) 1H NMR (400 MHz, DMSO-d6) delta 2.60 (6H, s), 7.09 (IH, d, J 8.3 Hz), 7.68 (IH, d, J2.0 Hz), 7.91 (IH, dd, J 8.3, 2.0 Hz), 1 1.44 (IH, s).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,3-Dioxoindoline-5-sulfonyl chloride, and friends who are interested can also refer to it.

Reference:
Patent; UNIVERSITY OF SOUTH FLORIDA; H. LEE MOFFITT CANCER CENTER AND RESEARCH INSTITUTE, INC.; WO2007/117699; (2007); A2;,
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. 324-03-8, name is 6-Fluoroindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 6-Fluoroindoline-2,3-dione

Exampie 1; 7-fluoro-3-hvdroxvquinolin-2{1H)-one; The title compound was prepared by the procedure depicted Sn Scheme 1 and described in detail below, using the general method of S-Y. Sit et al., Bioorqanic Medicinal Chem Lett.1996, beta, 499. Step 1. 6-Fluoro-1H-indo.e-2,3-dione (6-fluoroisatin, 200 mg, 1.2 mMoi), diethylamide (0.24 ml. 2.3 mMol), and ethyl diazoacetate (0,24 mL 2.3 mMol) were dissolved in ethanoi (15 mL) and stirred at room temperature for 64 hours. Removal of solvent in vacuo then provided the diazo intermediate as an Oil (LCMS m/z 278.0 [M-1]); this was treated with hydrochloric acid (1N, 75 rnL), and allowed to react for 40 hours at room temperature Filtration of the reaction mixture yielded ethyl 7-f.uoro-3- hydroxy-2-oxo-1.2-dihyo’roquinoiine-4-carboxylate as an orange solid (144 mg, 0.57 mMol). LCMS m/z 252.1 (M+1). 1H NMR (400 MHz, CD3OD) delta 1.42 (t, J^7,0 Hz13H), 4.48 (q, J =7.0 Hz, 2H)8 7.02 (m, 2H), 7.87 (del. J =5.6. 8.9 Hz, 1H).

The synthetic route of 324-03-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; DUPLANTIER, Allen Jacob; GAN, Xinmin; HU, Lain-Yen; LU, Jiemin; SHEEHAN, Susan Mary Kult; WO2010/58314; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem