Month: April 2021

Related Products of 239463-85-5,Some common heterocyclic compound, 239463-85-5, name is (R)-3-(5-(2-Aminopropyl)-7-cyanoindolin-1-yl)propyl benzoate (2R,3R)-2,3-dihydroxysuccinate, molecular formula is C26H31N3O8, 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 slurry of SI-I (769 g, 1.50 mol) as the tartrate salt (e.e. 98.3%) in dichloromethane (2 L) was added dropwise an aqueous solution of sodium hydroxide (5 N, 126 g, 3.15 mol) at 10 C, all in a round bottom flask (5 L). The reaction mixture was stirred until the pH was 11. The organic layer was separated and the aqueous layer was extracted with dichloromethane twice (500 ml 2). The combined organic layer was washed with water to neutrality, dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to give the SI-II (531 g, 97.5%, HPLC 98.2%) as a light yellow oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (R)-3-(5-(2-Aminopropyl)-7-cyanoindolin-1-yl)propyl benzoate (2R,3R)-2,3-dihydroxysuccinate, its application will become more common.

Reference:
Article; Liu, Hui; Lv, Fei; Liu, Yuan; Organic Preparations and Procedures International; vol. 51; 3; (2019); p. 287 – 293;,
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17564-64-6, name is 2-(Chloromethyl)isoindoline-1,3-dione, belongs to indolines-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Application In Synthesis of 2-(Chloromethyl)isoindoline-1,3-dione

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. 7.1.60 2-((2-(2-(Heptan-3-ylidene)hydrazono)-4-oxothiazolidin-3-yl)methyl)isoindoline-1,3-dione (8C) White powder, mp 70-74 C, 86% yield; 1H NMR (400 MHz, CDCl3): delta 0.82-0.93 (m, 2H, CH2, 3H, CH3), 1.08-1.12 (m, 1H, CH2), 1.30-1.37 (m, 3H, CH3), 1.51-1.55 (m, 1H, CH2), 2.24-2.32 (m, 2H, CH2), 2.36-2.44 (m, 2H, CH2), 3.82 (s, 2H, CH2, thiazolidinone), 5.71 (s, 2H, ArCH2), 7.73-75 (m, 2H, Ar), 7.85-7.86 (m, 2H, Ar).

The synthetic route of 17564-64-6 has been constantly updated, and we look forward to future research findings.

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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Related Products of 19155-24-9, 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 19155-24-9 as follows.

Preparation of l-(3-chloropropyl)-3,3-dimethylindolin-2-one; [0231] A solution of 3,3-dimethylindolin-2-one (1.843 g, 11.43 mmol, 1 equiv) in N,N- dimethylformamide was cooled to 0¡ãC. Sodium hydride (60percent dispersion) (503 mg, 12.58 mmol, 1.1 equiv) was slowly added and the reaction was stirred as such until all bubbling had stopped. 1 – bromo-3-chloropropane (3.37 ml, 34.3 mmol, 3 equiv) was added to the reaction mixture in one portion. The reaction was allowed to warm to ambient temperature and stirred as such for 16 h. The crude mixture was partitioned between ethyl acetate and water. The organic layer was dried over MgSO i, filtered, concentrated, and the residue was purified using the Biotage flash chromatography system (SNAP 50 g cartridge, R/= 0.5, gradient – 5percent>-30percent> ethyl acetate in hexanes) to afford the title compound as a light orange oil (2.38 g, 87percent); ‘i/NMR (400 MHz, DMSO-i/6): delta 1.26 (s, 6H); 1.98-2.14 (m, 2H); 3.65 (t, 2H, J= 6 and 6.8 Hz); 3.77-3.81 (m, 2H); 7.02-7.07 (m, 2H); 7.24-7.28 (m, 1H); 7.33-7.35 (m, 1H); MS for C13H16C1N0 m/z 237.99 (M+H)+.

According to the analysis of related databases, 19155-24-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ALTOS THERAPEUTICS, LLC; LUEHR, Gary, W.; SUNDARAM, Arathi; JAISHANKAR, Priyadarshini; PAYNE, Philip, W.; DRUZGALA, Pascal; WO2011/160084; (2011); A1;,
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Related Products of 603-62-3, 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. 603-62-3, name is 3-Nitrophthalimide belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Intermediate 1; Preparation of (2-methyl-l,3-dioxo-2,3-dihydro-lH-isoindol-4-yl)acetic acid; Step 1 : 4-Amino-l,3-isoindolinedione; A solution of 3-nitrophthalimide in ethylacetate was treated with 10% palladium on charcoal (10 wt. %) and hydrogenated at 20 psi for 2h. The catalyst was filtered through celite and the filterate was evaporated to give the crude product (97%) which was used without purification in the next step. 1H-NMR (delta ppm, DMSO-J6, 300 MHz): 10.85 (br. s, IH); 7.39 (t, J = 7.8, IH); 6.93 (d, J = 8.4, IH); 6.88 (d, J = 6.9); 6.38 (br. s, 2H).

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, 3-Nitrophthalimide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLENMARK PHARMACEUTICALS, S. A.; WO2009/118596; (2009); A2;,
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Synthetic Route of 334952-09-9, 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. 334952-09-9, name is 2-Oxoindoline-6-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows.

Intermediate 2a (2Og) is dissolved in DMF (15OmL) and carbonyldiimidazole (19g) is added. The reaction is then heated to 70C for 1 hour after which the reaction is cooled to room temperature. Aminoacetaldehyde diethylacetal (16.5mL) is added and allowed to react at room temperature overnight. The solvent is then removed under reduced pressure and the residue is purified by LC (SiO2, DCM:MeOH 90: 10) to yield the desired compound 1 (1 Og).

The chemical industry reduces the impact on the environment during synthesis 2-Oxoindoline-6-carboxylic acid. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG; WO2006/64044; (2006); A1;,
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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., Formula: C8H4ClNO2

General procedure: The mixture of isatin (1 mmol), 3-amino-1-phenyl-1H-pyrazol-5(4H)-one (1 mmol), 1,2-diarylethan-1-one, 2,3-dihydroinden-1-one (1 mmol) or 3,4-dihydronaphthalen-1(2H)-one (1 mmol), H2O (6 mL), HOAc (2 mL) was put in a reaction flask under 90 ¡ãC about 5-7 h (monitored by TLC). After completion, the reaction mixture was cooled to room temperature and the products would be isolated out at same time. Then, compound 4 was recrystallized from DMF, however, the pure products of 6 and 8 were filtered from water, dried, without further recrystallization.

According to the analysis of related databases, 7477-63-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wang, Zhansheng; Gao, Lingli; Xu, Zhongyun; Ling, Zhi; Qin, Yaqi; Rong, Liangce; Tu, Shu-Jiang; Tetrahedron; vol. 73; 4; (2017); p. 385 – 394;,
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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 16800-68-3 as follows. Quality Control of 1-Acetylindolin-3-one

General procedure: To a solution of 1a (35 mg, 0.2 mmol) and 2a (52.4 mg,0.4 mmol) in DCE (3 mL) was added iodine (10 mg, 0.04 mmol). The reaction mixture was heated at 80 C for 24 h, then cooled to room temperature and quenched with saturated sodium thiosulfate. The mixture was extracted with CH2Cl2, the combined organic layer was dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel to afford title compound.

According to the analysis of related databases, 16800-68-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Guo, Jing; Weng, Jiang; Huang, Gong-Bin; Huang, Lin-Jie; Chan, Albert S.C.; Lu, Gui; Tetrahedron Letters; vol. 57; 49; (2016); p. 5493 – 5496;,
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480-91-1, name is Isoindolin-1-one, belongs to indolines-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Application In Synthesis of Isoindolin-1-one

Isoindolin-1-one 21 (250mg, 1.85mmol) was dissolved in acetonitrile (9mL) and cesium carbonate (2.40g, 7.39mmol) was added followed by propargyl bromide (308muL, 2.77mmol). The reaction mixture was stirred at reflux (2h). The reaction mixture was then dissolved in CH2Cl2 (10mL) and washed with water (3¡Á15mL). The organic layer was dried (Na2SO4), filtered and concentrated under reduced pressure. Gravity-column chromatography of the residual oil (hexane/ethyl/acetate, 2:1) gave 27 as a yellow solid (205mg, 65%): mp 79-81C; Rf 0.66 (ethyl acetate); 1H NMR (400MHz, CDCl3) delta 7.82 (dJ=8.0Hz, 1H), 7.52 (dd J=8.0, 7.2Hz, 1H) 7.41-7.45 (m, 2H), 4.47 (s, 2H), 4.24 (s, 2H), 2.28 (s, 1H). 13C NMR (100MHz, CDCl3) delta 167.9, 141.2, 132.1, 131.6, 128.1, 123.8, 122.8, 78.1, 72.5, 49.1, 31.7. IR (neat) 3290, 3243, 2118, 1701cm-1; HRMS (ESI-TOF) m/z [M+H]+; calculated for C11H10NO 172.0762, Found: 172.0857.

The synthetic route of 480-91-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ronnebaum, Jarrid M.; Luzzio, Frederick A.; Tetrahedron; vol. 72; 40; (2016); p. 6136 – 6141;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 20876-36-2,Some common heterocyclic compound, 20876-36-2, name is 5-Aminoindolin-2-one, molecular formula is C8H8N2O, 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.

153 mg (0.490 mmol) (5-Bromo-2-chloro-pyrimidin-4-yl)-phenethyl-amine was taken into 0.5 mL 1,4 dioxane with 0.14 mL (1.00 mmol) diisopropylethylamine and 80 mg (0.539 MMOL) 5-amino-1, 3-DIHYDRO-INDOL-2-ONE. The reaction was allowed to heat to 110 C for sixteen hours. The resulting brown glass was taken into 92.3 : 7: 0.7 CHCI3 : CH30H: NH40H and washed with 1 N sodium hydroxide. The organic layer was dried over magnesium sulfate and evaporated directly onto silica gel. This adsorbed compound was purified via column chromatography (97.8 : 2: 0.2 CHCI3 : CH30H: NH40H) over silica to isolate the major product.the title compound was isolated as a white solid. c2ohigbrn50 : ms: 424.2/426. 2 (mh+) ;’h nmr (d6-dmso) 10.20 (s, 1 h), 9.01 (s, 1 h), 7.93 (s, 1 h), 7.52 (s, 1 h), 7.44 (d, j = 8.4 hz, 1 h), 7.28-7. 16 (m, 5 h), 6.97 (m, 1 h), 6.65 (d, j=8. 3hz, 1 h), 3.56 (m, 2 h), 3.31 (s, 2 h), 2.82 (t, j=7. 9hz, 2h) ppm.

The synthetic route of 20876-36-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2004/56786; (2004); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 52351-75-4, These common heterocyclic compound, 52351-75-4, name is 6-Methoxyindoline-2,3-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: Compound 16 (1.0 g, 5.65 mmol)Ethanol (1.6 mL)And a 10 N aqueous solution of sodium hydroxide (6 mL) was heated to 85 C.,Ethanol (10.4 mL)2-Acetoxyacetophenone (1.3 g, 7.35 mmol) dissolved in water was added.After stirring at 85 C. for 1 hour,Water (20 mL) was added under ice cooling,1N Hydrochloric acid was added until pH 1 was reached.The precipitate was collected by filtration, washed with water and ethanol: acetonitrile (1: 1) solution,Compound 17 was obtained as a red solid (1.2 g, 74%).

The synthetic route of 52351-75-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KYOTO UNIVERSITY; OISHI, SHINYA; OHNO, HIROAKI; FUJII, NOBUTAKA; YAMAMOTO, KOUKI; (43 pag.)JP2017/81888; (2017); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem