Indolines-derivatives

These common heterocyclic compound, 446292-07-5, name is (R)-2-(2-Hydroxy-3-((4-(3-oxomorpholino)phenyl)amino)propyl)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. name: (R)-2-(2-Hydroxy-3-((4-(3-oxomorpholino)phenyl)amino)propyl)isoindoline-1,3-dione

To suspension of 2-[(2R)-2-hydroxy-3-{[4-(3-oxomorpholin-4-yl)phenyl]amino}propyl]-1H-isoindole-1,3(2H)-dione (170 gm) and potassium carbonate (59.3 gm) in dichloromethane (1500 ml) was added 1,1?-carbonylbis(1H-imidazole) (153.4 gm) at room temperature. Reaction mass was then stirred for 5 hr at room temperature. After completion of reaction, inorganic base is removed by filtration. The obtained filtrate is concentrated under reduced pressure to yield solid. To this solid tetrahydrofuran (850 ml) was added followed by stirring and filtration. The obtained solid is dried under vacuum for 4 hr at 50 C to obtain 2-({(5S)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)-1H-isoindole-1,3(2H)-dione. [Yield = 160 gm (88.2 %); Purity (HPLC) =99.65 %]

The synthetic route of (R)-2-(2-Hydroxy-3-((4-(3-oxomorpholino)phenyl)amino)propyl)isoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEGAFINE PHARMA (P) LTD; MATHAD Vijayavitthal Thippannachar; PATIL NILESH SUDHIR, Nilesh; NIPHADE NAVNATH CHINTAMAN, Navnath; MALI ANIL CHATURLAL, Anil; BODAKE MAHENDRA BHAGIRATH, Mahendra; IPPAR SHARAD SUBHASH, Sharad; TALLA RAJESH, Rajesh; WO2013/121436; (2013); A2;,
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Electric Literature of 104618-32-8,Some common heterocyclic compound, 104618-32-8, name is 2-(4-Oxocyclohexyl)isoindoline-1,3-dione, molecular formula is C14H13NO3, 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.

4-Cyanophenyl hydrazine hydrochloride (4.41 g, 0.026 mole) was dissolved in acetic acid (100 ml) and sodium acetate (2 g) was added. 4-Phthalimido cyclohexanone (6.4 g, 0.026 mole) was added and the mixture heated under reflux overnight. The solvent was removed in vacuo and the residue triturated with methanol to give 3-phthalimido-6-cyano-1,2,3,4-tetrahydrocarbazole as a beige solid, (5.3 g).

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-Oxocyclohexyl)isoindoline-1,3-dione, its application will become more common.

Reference:
Patent; SMITHKLINE BEECHAM PLC; EP603432; (1994); A1;; ; Patent; Smithkline Beecham plc; US5827871; (1998); A;; ; Patent; SmithKline Beecham P.L.C.; US5464864; (1995); A;,
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Related Products of 5428-09-1, 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. 5428-09-1, name is 2-Allylisoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To the mixture of B(C6F5)3 (5.0molpercent) and cyclic imides (1.0mmol) in dioxane, was added PhSiH3 (3.0mmol) slowly under an atmosphere of nitrogen. The reaction mixture was stirred and refluxed at 110°C under an atmosphere of nitrogen. After the imide was consumed completely (detected by TLC) the mixture was added with aqueous ammonia (15mL) and extracted with CH2Cl2 (10mL×3). The combined organic phase was dried over Na2SO4, after removing the solvent under vacuum, the residue was purified by column chromatography to give the product.

The synthetic route of 2-Allylisoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ding, Guangni; Wu, Xiaoyu; Lu, Bin; Lu, Wenkui; Zhang, Zhaoguo; Xie, Xiaomin; Tetrahedron; vol. 74; 11; (2018); p. 1144 – 1150;,
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These common heterocyclic compound, 6341-92-0, name is 6-Chloroisatin, 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. Application In Synthesis of 6-Chloroisatin

General procedure: In a 25 mL round bottom flask, isatins 1 (1 mmol), 3-phenylisoxazol-5(4H)-one 2 (1 mmol) or 3-ethylisoxazol-5(4H)-one 7 (1 mmol), pyrazol-5-amine 3 (1 mmol) or 6-aminopyrimidine-2,4-(1H,3H)-dione 5 (1 mmol), and Amberlyst-15 (100 mg) were stirred in CH3OH (5.0 mL) at 80 C. When the reaction was completed (detected by TLC), the spherical catalyst was separated by a sieve at once under hot condition. Then, the reaction mixture was cooled to room temperature, and solid precipitation occurred. After filtration, the crude product was recrystallized from EtOH and DMF to give pure compound.

The synthetic route of 6-Chloroisatin has been constantly updated, and we look forward to future research findings.

Reference:
Article; Niu, Qingqing; Xi, Junhua; Li, Lei; Li, Li; Pan, Chengli; Lan, Meijun; Rong, Liangce; Tetrahedron Letters; vol. 60; 43; (2019);,
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Adding a certain compound to certain chemical reactions, such as: 201940-08-1, name is tert-Butyl 5-bromoisoindoline-2-carboxylate, 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 201940-08-1, Computed Properties of C13H16BrNO2

0.69 ml of n-Butyl lithium (2.5M solution in hexane) was added dropwise to a stirred solution of 5-bromo-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester (429 mg; 1.44 mmol) in anhydrous THF (10 ml) at -78 C. under an atmosphere of nitrogen. The reaction was stirred for 50 minutes then 1-methyl-4-piperidone (212 mul; 1.2 equiv.) was added and stirred at -78 C. for a further 60 minutes then warmed to room temperature. The reaction was quenched with saturated ammonium chloride solution then extracted with EtOAc. The EtOAc layer was washed with saturated NaHCO3, brine, dried (MgSO4) and evaporated. Purification by flash column chromatography on SiO2, gradient elution from 0% to 10% 2M methanolic ammonia/DCM gave 111 mg of 5-(4-hydroxy-1-methyl-piperidin-4-yl)-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester as a colourless oil.

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; ASTEX THERAPEUTICS LIMITED; US2010/152184; (2010); A1;,
Indoline – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 104618-31-7, name is 2-(4-Hydroxycyclohexyl)isoindoline-1,3-dione, 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 104618-31-7, Recommanded Product: 2-(4-Hydroxycyclohexyl)isoindoline-1,3-dione

[00487] To a solution of PPh3 (1 .28 g, 4.9 mmol) in THF (12 mL) was added dropwise DEAD (852 mg, 4.9 mmol) at -10C. After the white solid was appeared, compound 2-(4-hydroxycyclohexyl)isoindoline-1 ,3-dione (600 mg, 2.45 mmol) was added, followed by CH3COSH (0.35 mL, 4.9 mmol) at -10C. The mixture was stirred at room temperature overnight. TLC (PE: EA = 1 :1 ) showed the reaction was complete. The mixture was poured into water (200 mL) and extracted with EtOAc (100 mL). The aqueous layer was extracted with EtOAc (100 mL X 3). The combined extracts were dried over Na2SO4, filtered and concentrated in vacuo to give S-(4-(1 ,3-dioxoisoindolin-2-yl)cyclohexyl) ethanethioate (600 mg, 81 %) as a white solid

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

Reference:
Patent; TOLERO PHARMACEUTICALS, INC.; XU, Yong; BRENNING, Benjamin, Gary; KULTGEN, Steven, G.; LIU, Xiaohui; SAUNDERS, Michael; HO, Koc-Kan; WO2013/13188; (2013); A1;,
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Some common heterocyclic compound, 17564-64-6, name is 2-(Chloromethyl)isoindoline-1,3-dione, molecular formula is C9H6ClNO2, 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. Recommanded Product: 2-(Chloromethyl)isoindoline-1,3-dione

0.45 g of potassium carbonate (1.1equiv) were added to a stirring solution of saccharin (500mg, 1.0equiv) in 20mL of N,N-dimethylformamide at room temperature. N-(Chloromethyl)phthalimide (0.54g, 1.0equiv) was added and the reaction stirred at 80C for 72h. The reaction was poured on ice. The aqueous phase was extracted with ethyl acetate (3×50mL), the organics were reunited, dried over sodium sulfate and evaporated in vacuo. Purification via column chromatography on silica gel (ethyl acetate-n-hexane 2:1) gave title compound as a white solid (0.61mg, 66% yield); mp 284-287C; IR numax 1725 (nu C=O), 1337 (nuas S=O), 1252 (nu C-N), 1166 (nus S=O), 727 (delta Csp2-H), 677 (delta Csp2-H) cm-1; 1H NMR (400MHz, DMSO-d6) delta 5.66 (2H, s, CH2), 7.90 (2H, m, 2×CHAr), 7.97 (m, 2H, 2×CHAr), 8.02 (1H, t, J=7.6Hz, CHAr), 8.07 (1H, t, J=7.6Hz, CHAr), 8.19 (1H, d, J=7.6Hz, CHAr), 8.28 (1H, d, J=7.6Hz, CHAr); 13C NMR (101MHz, DMSO-d6) delta 41.8 (CH2), 122.0 (Ar),124.1 (Ar), 126.0 (Ar), 126.15 (Ar), 131.6 (Ar), 135.6 (Ar), 135.9 (Ar), 136.7 (Ar), 137.1 (Ar), 157.75 (C=O), 166.9 (C=O).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 17564-64-6, its application will become more common.

Reference:
Article; D’Ascenzio, Melissa; Carradori, Simone; De Monte, Celeste; Secci, Daniela; Ceruso, Mariangela; Supuran, Claudiu T.; Bioorganic and Medicinal Chemistry; vol. 22; 6; (2014); p. 1821 – 1831;,
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Related Products of 6341-92-0,Some common heterocyclic compound, 6341-92-0, name is 6-Chloroisatin, molecular formula is C8H4ClNO2, 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 isatin 1a (0.1 mmol), (E)-4-phenylbut-3-en-2-one (2a, 0.1 mmol), arginine (0.01 mmol) in MeOH (1.0 mL) was stirred for 48 h at 25 C. After completion of the reaction (TLC), the solvent was removed under vacuum. The crude product was subjected to column chromatography on silica gel using petroleum ether/ethyl acetate = 1:1 as the eluent to give 3a.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Chloroisatin, its application will become more common.

Reference:
Article; Yan, Tingting; Wang, Xiaoyan; Sun, Hongbao; Liu, Jie; Xie, Yongmei; Molecules; vol. 18; 12; (2013); p. 14505 – 14518;,
Indoline – Wikipedia,
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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 2436-29-5 as follows. COA of Formula: C11H9NO3

Step 11. 2-(3-{[1-(3-Benzyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-2-yl)-2-methylpropyl]amino}propyl)-1H-isoindole-1,3(2H)-dione; The product from Step 10 (20), 42 mg (0.13 mmol) was dissolved in anhydrous CH2Cl2 followed by the addition of phthalimide protected 3-aminopropionaldehyde 33 mg (0.16 mmol) and 37 mg (0.18 mmol) of sodium acetoxyborohydride and finally 10 mul (0.18 mmol) of acetic acid. The reaction was left stirring at room temperature for 2.5 h. The solvent was evaporated and the product redissolved in ethyl acetate and washed with saturated NaHCO3 and brine. The organic layer was dried over MgSO4, filtered and concentrated and dried under high vacuum resulting in 63 mg (0.13 mmol, 94%) of 2-(3-{[1-(3-benzyl-4-oxo-a]pyrimidin-2-yl)-2-methylpropyl]amino}propyl)-1H-isoindole-1,3(2H)-dione (21) as a white solid.

According to the analysis of related databases, 2436-29-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chiron Corporation; US2005/228002; (2005); A1;,
Indoline – Wikipedia,
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Electric Literature of 39603-24-2, 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. 39603-24-2, name is 5,7-Dimethylindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Indole-2,3-dione 1 (1 mmol) and 1,2-diamine 2 (1 mmol) and 5 mol% of Cu doped CdS NPs in ethylene glycol (10 ml) was introduced in a 50 ml round-bottomed flask. The flask was placed in the microwave cavity and subjected to irradiation for appropriate time at 80 C using a maximum power of 300 W. When the reaction was complete, the reaction mixture was extracted with ethylacetate; the organic layer was removed under reduced pressure to afford the crude product. The pure products were obtained by crystallization from ethanol.

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, 5,7-Dimethylindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Dandia, Anshu; Parewa, Vijay; Maheshwari, Shuchi; Rathore, Kuldeep S.; Journal of Molecular Catalysis A: Chemical; vol. 394; (2014); p. 244 – 252;,
Indoline – Wikipedia,
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