Tag: M.W=200-300

Related Products of 552330-86-6, These common heterocyclic compound, 552330-86-6, name is 5-Bromoisoindolin-1-one, 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.

Argon was purged to a stirring solution of 5-bromoisoindolin-l-one (200 mg, 0.943 mmol) in dimethylformamide for 30 min, to this bis(pinacolato)diboron (477 mg, 1.886 mmol) and tetrakis(triphenylphosphine) palladium(O) (13 mg, 0.018 mmol) and potassium acetate (277 mg, 2.829 mmol) were added and the reaction mixture was heated to 70 C for 16 h. The reaction mixture was cooled to RT, filtered through celite and the filtrate was extracted with ethyl acetate (3 x). The combined ethyl acetate layers were washed with brine, dried over sodium sulphate and concentrated under reduced pressure to afford the title compound as a solid (100 mg, 41 %).

Statistics shows that 5-Bromoisoindolin-1-one is playing an increasingly important role. we look forward to future research findings about 552330-86-6.

Reference:
Patent; LEO PHARMA A/S; NIELSEN, Simon Feldbaek; HORNEMAN, Anne Marie; LAU, Jesper Faergemann; LARSEN, Jens Christian H°jland; WO2011/134468; (2011); A1;,
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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 2058-72-2 as follows. Formula: C9H6BrNO2

Example 12: Under nitrogen protection, copper powder (1.75 mmol) was sequentially added to a 10 ml reaction tube containing a magnet.1-methyl-5-nitroindole-2,3-dione (1.55 mmol), bromodifluoromethyl-1,3-benzoxazole (1.50 mmol),p-Toluenesulfonic acid (0.31 mmol) was added to dry NMP 4.0 ml and reacted at 80 C for 6 hours.After the reaction was stopped, the solid in the reaction mixture was filtered through a short silica gel column, and the filtrate was extracted with saturated brine and ethyl acetate.The organic layer was taken and dried over anhydrous sodium sulfate.Filter and concentrate. The crude product was separated and purified by column chromatography to give the desired product 3d, yield 82%.

According to the analysis of related databases, 2058-72-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shanghai University; Jiang Haizhen; Zhang Tiantian; Miao Feng; Wang Dejing; Zhang Qian; Wang Wei; (21 pag.)CN108467391; (2018); A;,
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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. 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-one, A new synthetic method of this compound is introduced below., COA of Formula: C10H9Cl2NO

5. Preparation of ZPR in the melt of Na C03 decahydrate. To the melt of Na2C03 decahydrate (40g) was added BITP HCl (lOg) and CEI (10.35g) and the mixture was heated at 95 C for 10 hours. After 10 h the conversion to ZRP was 88. 2% (% area by HPLC). To the reaction mixture water was added and the solid was filtrated and washed with water. After drying the solid weighs 17.14g (purity by HPLC 88%).; 7. Preparation of ZPR in the presence of NaCl. In a three necked flask was charged 40 ml brine, BITP HC1 (14. 1g), CEI (10.35g) and Na2C03 (14. 1g) ; the mixture was than heated at 90C for 16hours. After this the mixture was cooled, water was added and the solid was filtrated, washed with water and dried. The product weights after drying 16.9g (purity by HPLC 87.5%).

The synthetic route of 118289-55-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TEVA PHARMACEUTICAL INDUSTRIES LTD.; TEVA PHARMACEUTICALS USA, INC.; WO2005/40160; (2005); A2;,
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Application of 99365-40-9, A common heterocyclic compound, 99365-40-9, name is 6-Bromoindolin-2-one, molecular formula is C8H6BrNO, 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.

Commercially available 6-bromoxindole (656 mg), zinc cyanide (288 mg) and tetrakis triphenylphosphine palladium(0) (175 mg) were suspended in dry N,N-dimethylformamide (6 mL). The resulting mixture was degassed by three pump/vent cycles with argon and then placed in a preheated oil bath (80 C.). After stirring at this temperature for 15 h the mixture was cooled to room temperature, diluted with water (60 mL) and extracted with ethyl acetate (3×60 mL). The combined organic layers were washed with water (2×60 mL), dried (MgSO4), filtered and concentrated. The remaining residue was purified by flash chromatography (silica, dichloromethane/methanol) to afford the title compound (385 mg; 81%). [MH]+=159.

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; Alantos Pharmaceuticals, Inc.,; US2006/173183; (2006); A1;,
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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 675109-26-9 as follows. Application In Synthesis of 6-Bromoisoindolin-1-one

A mixture of 6-bromoisoindolin-1-one (1.0 g, 4.72 mmol), Pd(dppf)Cl2 (104 mg, 0.14 mmol), K2CO3 (1.96 g, 14.2 mmol) and 3-pyridylboronic acid (580 mg, 4.72 mmol) in dioxane (45 mL) and water (5 mL) was heated to 100 C. overnight. After cooling, the mixture was poured into water and extracted with EtOAc (3×100 mL). The combined organic fractions were washed with brine and dried over sodium sulfate. The solvent was evaporated and the residue was purified by column chromatography on silica gel (1%-50% EtOAc in pet. ether) to afford 85B (500 mg, 50% yield) as an off-white solid: 1H NMR (400 MHz, DMSO-d6) delta 8.94 (d, J=2 Hz, 1H), 8.67 (s, 1H), 8.60 (dd, J=4.8 Hz, 1.2 Hz, 1H), 8.16-8.13 (m, 1H), 7.96-7.94 (m, 2H), 7.71 (d, J=8.8 Hz, 1H), 7.52-7.49 (m, 1H), 4.44 (s, 2H); ESI m/z 211.0 [M+H]+.

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; Seal Rock Therapeutics, Inc.; BROWN, Samuel David; US2018/291002; (2018); A1;,
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Electric Literature of 169037-23-4, These common heterocyclic compound, 169037-23-4, name is 5-(Trifluoromethoxy)indoline-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: A mixture of 5,6-dimethoxy-2-[(E)-1-arylmethylidene]-1-indanone (1, 0.364 mmol), thiazolidine-4-carboxylic (3, 0.364 mmol) and 1-morpholinoindoline-2,3-dione (2,0.364 mmol) was dissolved in methanol (1 mL) and irradiated for 2-3.5 min in a CEM microwave synthesizer (100 0C, 100 W). After completion of the reaction as evident from TLC, the mixture was poured into water. The precipitated solid was filtered and washed with water to afford the products 4a-i which was purified by recrystallisation.

The synthetic route of 169037-23-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Almansour, Abdulrahman I.; Ali, Sadath; Ali, Mohamed Ashraf; Ismail, Rusli; Choon, Tan Soo; Sellappan, Velmurugan; Elumalai, Karthi Keyan; Pandian, Suresh; Bioorganic and Medicinal Chemistry Letters; vol. 22; 24; (2012); p. 7418 – 7421;,
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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. 6941-75-9, name is 5-Bromoisoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., category: indolines-derivatives

280 ml of 1M 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 00C 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-1 H-isoindole as a dark brown gummy solid. 1H NMR (DMSO-d6) 7.45 (1 H, s), 7.36 (1H, d), 7.20 (1H, d), 4.05 (4H, s).

According to the analysis of related databases, 6941-75-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; WO2008/44041; (2008); A1;,
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Synthetic Route of 868066-91-5, A common heterocyclic compound, 868066-91-5, name is 5-Bromo-2-methylisoindolin-1-one, molecular formula is C9H8BrNO, 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.

Synthesis of 2-methyl-5-((9-((2-(trimethylsilyl)ethoxy)methyl)-9H-purin-6-yl)amino)isoindolin-1-one (4) Procedure A: A mixture of 9-((2-(trimethylsilyl)ethoxy)methyl)-9H-purin-6-amine (3, 0.10 g, 0.37 mmol), 5-bromo-2-methylisoindolin-1-one (2, 0.10 g, 0.45 mmol), sodium tert-butoxide (54 mg, 0.56 mmol) and XPhos (5 mg, 0.01 mmol) in toluene (10 mL) was degassed with argon for 30 min. Tris(dibenzylideneacetone)dipalladium(0) (20 mg, 0.022 mmol) was added under argon atmosphere and the reaction mixture was heated at 100° C. for 12 h. After completion of the reaction, the reaction mixture was filtered through celite pad and the filtrate was concentrated. The crude residue was purified by silica gel column chromatography using 0-10percent ethyl acetate in hexanes as eluent to afford 2-methyl-5-((9-((2-(trimethylsilyl)ethoxy)methyl)-9H-purin-6-yl)amino)isoindolin-1-one (4). Yield: 0.11 g, 71percent; MS (ESI) m/z 411 [M+1]+.

The synthetic route of 868066-91-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; eFFECTOR Therapeutics, Inc.; Sprengeler, Paul A.; Reich, Siegfried H.; Ernst, Justin T.; Webber, Stephen E.; Shaghafi, Mike; Murphy, Douglas; Tran, Chinh; (131 pag.)US10112955; (2018); B2;,
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Reference of 5181-35-1,Some common heterocyclic compound, 5181-35-1, name is 2-(2-Bromoethoxy)isoindoline-1,3-dione, molecular formula is C10H8BrNO3, 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 clean dry flask containing suspension of 2-(2-bromoethoxy)isoindoline- l,3-dione (30 g, 0.111 mol), 1H- 1,2,3 triazole (7.66 g, 111 mmol) in dimethylformamide (150 ml) was added cesium carbonate ((36 g, 111 mmol) portion wise at room temperature under stirring. After 17 hours, the reaction mixture was filtered and filtrate was slowly poured into chilled water (1050 ml) under stirring. After 30 minutes of stirring, the separated precipitates were collected by filtration and washed with water (100 ml). The collected precipitates were dried at 40 C for 2 hours under high vacuum to obtain 18.5 g of a mixture of 2-[2-(2H- l,2,3-triazol-2-yl)ethoxy]- lH-isoindole- l,3(2H)-dione and 2-[2- (lH- l,2,3-triazol- l-yl)ethoxy]- lH-isoindole- l,3(2H)-dione as a white compound in 65% yield. Analysis: Mass: 259.2 (M+l); for Molecular weight: 258 and Molecular formula: C12H10N4O3; To a solution of mixture of 2-(2-(2H-l,2,3-triazol-2- yl)ethoxy)isoindoline-l,3-dione and 2-(2-(lH-l,2,3-triazol-l-yl)ethoxy)isoindoline-l,3-dione (13 g, 50.3 mmol, obtained from Step 1) in dichloromethane (130 ml) was added hydrazine hydrate (3.7 ml, 75.7 mmol) under stirring at room temperature. After 2 hours, the progress of reaction was monitored by thin layer chromatography using mixture of chloroform and methanol as solvent system. After completion of the reaction the unwanted solid was filtered out and washed with dichloromethane (25 ml). The collective filtrates were concentrated at 40 C under high vacuum to dryness to provide 6.5 g of a mixture of 2-[2-(aminooxy)ethyl]-2H-l,2,3-triazole and l-[2- (aminooxy)ethyl]-lH-l,2,3-triazole, which was used as such in the next step without any further purification; To a solution of sodium salt of (25,5 ?)-6-(benzyloxy)-7-oxo-l,6-diaza-bicyclo[3.2.1]octane-2-carboxylic acid (15 g, 54.3 mmol, prepared as per the procedure disclosed in International Patent Application No. PCT/IB2013/059264) in dimethylformamide (75 ml) was added EDC.HC1 (15.6 g, 81.6 mmol) at ambient temperature under stirring. Then N-methyl morpholine (16.5 ml, 0.150 moles) was added followed by HOBT (7.73 g, 50.7 mmol) and reaction mixture was stirred for 5 minutes at ambient temperature. To this reaction mixture was added a solution of mixture of 2-[2-(aminooxy)ethyl]- 2H-l,2,3-triazole and l-[2-(aminooxy)ethyl]-lH-l,2,3-triazole (6.5 g, product from Step 2) in dimethylformamide (6.5 ml) under stirring at 15 C and then allowed to attain room temperature. The progress of reaction was monitored by thin layer chromatography using mixture of chloroform and methanol (9: 1) as solvent system. After completion of the reaction (17 hours), the resulted reaction mixture was slowly poured into chilled water (500 ml) and extracted with ethyl acetate (2×150 ml). The combined organic layer was washed with brine (75 ml) and organic layer was dried over anhydrous sodium sulfate, concentrated on rotavapour to provide 17.5 g of crude compound. It was purified by column chromatography (silica gel 60-120 mesh) using mixture of hexane and acetone as an eluent. The upper spot containing fractions were collected at 30-40% concentration of acetone in hexane and concentrated to dryness under vacuum to provide7.5 g of (25,5 ?)-6-(benzyloxy)-7-oxo-N-[2-(2H-l,2,3-triazol-2-yl)ethoxy]-l,6-diazabicyclo [3.2.1]octane-2- carboxamide. Similarly lower spot containing fractions collected at 40-50% concentration of acetone in hexane were concentrated to dryness under vacuum to provide 5.2 g of of (25,5 ?)-6- (benzyloxy)-7-oxo-N-[2-(lH-l,2,3-triazol-l-yl)ethoxy]-l,6-diazabicyclo[3.2.1]octane-2- carboxamide. In total, 12.7 g was obtained in 70% yield. Analysis: Mass: 385.3 (M-l); for Molecular weight: 386 and Molecular formula: C18H22N6O4.

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

Reference:
Patent; WOCKHARDT LIMITED; TADIPARTHI, Ravikumar; PATIL, Vijaykumar Jagdishwar; DEKHANE, Deepak; SHAIKH, Mohammad Usman; BIRAJDAR, Satish; DOND, Bharat; PATEL, Mahesh Vithalbhai; (100 pag.)WO2017/81615; (2017); A1;,
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Synthetic Route of 104618-31-7, 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. 104618-31-7, name is 2-(4-Hydroxycyclohexyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

(b) 4-(Phthalimido)-cyclohexanone 95 g (0.388 Mol) of 4-(phthalimido)cyclohexanol are dissolved in 600 ml of chloroform and, after the addition of 450 ml of water and 120 ml of sulfuric acid, 90 g (0.3 Mol) of potassium dichromate are added in batches. The internal temperature of the mixture is maintained at between 25 and 30 C. by slight cooling. The mixture is stirred for a further 3 hours, then the chloroform phase is separated of and the mixture extracted twice more with chloroform. After drying and concentration of the extracts 82 g (86.9% of theory) are obtained.

The synthetic route of 2-(4-Hydroxycyclohexyl)isoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dr. Karl Thomae GmbH; US4731374; (1988); A;,
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