Tag: M.W=200-300

Synthetic Route of 1254319-51-1,Some common heterocyclic compound, 1254319-51-1, name is 6-Bromo-2-methylisoindolin-1-one, molecular formula is C9H8BrNO, 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.

Potassium acetate (294 mg, 3.00 mmol), bis(pinacolato)diboron (305 mg, 1.200 mmol), 6-bromo-2- methylisoindolin-l-one (271 mg, 1.200 mmol) and 2nd Generation XPHOS precatalyst (59.0 mg, 0.075 mmol) were added to a 8 mL reaction vial equipped with a stir bar. The vial was evacuated and charged 3x with nitrogen. 1,4-Dioxane (8 mL) was added, the vial was again evacuated and charged (3x) with nitrogen, and the borylation reaction was heated to 100C. Monitored by LCMS; once borylation was complete the reaction was cooled to room temperature and 2-chloro-3 -(-(( 1- fluorocyclopentyl)methyl)-lH-pyrazol-4-yl)-6-methylpyridine (INTERMEDIATE F7; 294 mg, 1.0 mmol) and l, -bis(di-tert-butylphosphino)ferrocene palladium dichloride (48.9 mg, 0.075 mmol) were added to the reaction. The vial was evacuated and charged 3x with nitrogen, then added 3M aqueous K2C03 (1.0 mL, 3.00 mmol). The reaction was then heated to 70C overnight. LCMS shows reaction is substantially complete. Cooled to room temperature, then partitioned between water and ethyl acetate. The organic was filtered over a bed of sodium sulfate. The aqueous was extracted twice more with ethyl acetate, and the organic from those extractions was used to wash the sodium sulfate as well. The combined filtrate was evaporated and taken up again in DCM, then purified by silica gel chromatography, eluting with 20-100% 3 : 1 EtOAc:EtOH in hexanes. The major peak was isolated and the volatiles were evaporated. The solid was scraped to a small particle size and treated with diethyl ether. The suspension was filtered and the solid was collected as the title compound. MS: 405 (M+l). 1H NMR (500 MHz, CDC13): delta 7.89 (s, 1H), 7.67 (d, J=7.5 Hz, 1H), 7.58 (d, J=7.7 Hz, 1H), 7.39 (d, J=7.7 Hz, 1H), 7.21 (s, 1H), 7.18 (d, J=7.8 Hz, 1H), 7.04(s, 1H), 4.39 (s, 2H), 4.23 (d, J=21.6 Hz, 2H), 3.20 (s, 3H), 2.62 (s, 3H), 1-77-1.58 (m, 8H).

The synthetic route of 1254319-51-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MSD R&D (CHINA) CO., LTD.; ACTON, John, J., III; BAO, Jianming; DENG, Qiaolin; EGBERTSON, Melissa; FERGUSON, Ronald, III; GAO, Xiaolei; HARRISON, Scott Timothy; KNOWLES, Sandra, L.; LI, Chunsing; LO, Michael Man-Chu; MAZZOLA, Robert, D., Jr.; MENG, Zhaoyang; NA, Meng; RUDD, Michael, T.; SELYUTIN, Oleg, B.; TELLERS, David, M.; TONG, Ling; ZHANG, Fengqi; (195 pag.)WO2019/5587; (2019); A1;,
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Adding a certain compound to certain chemical reactions, such as: 667463-64-1, name is 6-Bromo-1-methylindoline-2,3-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 667463-64-1, Recommanded Product: 6-Bromo-1-methylindoline-2,3-dione

Step 2: Synthesis of Intermediate 1-12.2 1-12.1 (15.0 g, 63 mmol) and hydrazine hydrate (30 mL, 618 mmol) are heated to 125 C for 72 h. To the cool reaction mixture DCM is added and extracted with water and 1 M HC1. The organic layer is dried over MgSC>4 and concentrated. The crystallized residue is dissolved in DCM, methanol is added and the DCM is removed in vacuo. The crystallized product is filtered by sunction and washed with cold methanol. Yield 63%, m/z 226/228 [M+H]+, rt 1.16 min, LC-MS Method V001 003.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Bromo-1-methylindoline-2,3-dione, and friends who are interested can also refer to it.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ANDERSKEWITZ, Ralf; GRAUERT, Matthias; GRUNDL, Marc; HAEBEL, Peter, Wilhelm; OOST, Thorsten; PAUTSCH, Alexander; PETERS, Stefan; BINDER, Florian; VINTONYAK, Viktor; WO2014/140075; (2014); A1;,
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Reference of 1677-48-1, 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. 1677-48-1, name is 5,6-Dichloroindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

1.08 g of 4,5-dichloroindoloquinone and 1.08 g of 5,6-dichloroindole quinone were weighed into a 100 ml three-necked flask, 40 ml of dichloromethane, 0.38 g of sodium borohydride The reaction temperature: 40 , after the end of the reaction, the rotary evaporation to remove the solvent, the crystal to be purple solid 5,6,4 ‘, 5’-tetrachloroindiu red crude 1.03, the reaction time: 4.0h, reaction temperature: 40 , G, yield 51.5%.

The synthetic route of 5,6-Dichloroindoline-2,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Northwest University; Wang, Culing; Liu, Jianli; Zhao, Danqing; Liu, Zhulan; Zhang, Ning; (10 pag.)CN103980182; (2016); B;,
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Related Products of 87-48-9,Some common heterocyclic compound, 87-48-9, name is 5-Bromoindoline-2,3-dione, molecular formula is C8H4BrNO2, 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: TiCl4 (0.7 mL, 6 mmol)was added to a stirred suspension of Zn powder (0.78 g, 12 mmol) in freshlydistilled anhydrous THF (15 mL) at room temperature (rt) under a dry N2atmosphere. After completion of the addition, the mixture was refluxed for 2 h.The suspension of the low-valent titanium reagent thus-formed was cooled tort. A solution of isatin or its derivatives 1 or 3 (2 mmol) in THF (10 mL) wasadded dropwise. The mixture was stirred at room temperature for about 5 minunder N2. After this period, the thin layer chromatography (TLC) analysis of themixture showed the reaction completed. The reaction mixture was quenchedwith 3% HCl (15 mL) and extracted with CHCl3 (3 50 mL). The combinedextracts were washed with water (3 50 mL) and dried over anhydrousNa2SO4. After evaporation of the solvent under reduced pressure, the crudeproduct was purified by column chromatography (petroleum ether/ethylacetate = 5:1) to give the pure products 2 or 4.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromoindoline-2,3-dione, its application will become more common.

Reference:
Article; Lin, Wei; Hu, Ming-Hua; Feng, Xian; Fu, Lei; Cao, Cheng-Pao; Huang, Zhi-Bin; Shi, Da-Qing; Tetrahedron Letters; vol. 55; 14; (2014); p. 2238 – 2242;,
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These common heterocyclic compound, 954-81-4, name is N-(5-Bromopentyl)phthalimide, 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. HPLC of Formula: C13H14BrNO2

General procedure: A mixture of the intermediates 3a-3e (5 mmol) and corresponding secondary amine 4a-4g (5.5 mmol) was added in CH3CN (20 ml) at the presence of anhydrous K2CO3 (6 mmol). The mixture was heated at 65 C for 6-10 h. The solvent was evaporated in vacuo. The residue was dissolved in CH2Cl2 (25 mL), washed with water (20 mL ¡Á 3), and the combined organic phases were washed with saturated aqueous NaCl (30 mL), dried over sodium sulfate, and filtered. The solvent was evaporated under reduced pressure. The residue was purified on a silica gel chromatography using mixtures of petroleum/acetone as eluent to get the target products TM-1~TM-28.

The synthetic route of N-(5-Bromopentyl)phthalimide has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sang, Zhipei; Wang, Keren; Wang, Huifang; Yu, Lintao; Wang, Huijuan; Ma, Qianwen; Ye, Mengyao; Han, Xue; Liu, Wenmin; Bioorganic and Medicinal Chemistry Letters; vol. 27; 22; (2017); p. 5053 – 5059;,
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Adding a certain compound to certain chemical reactions, such as: 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-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 169037-23-4, Computed Properties of C9H4F3NO3

General procedure: A mixture of beta-nitrostyrenes, isatin and tyrosine (1:1:1) was stirredunder heating at 100 C for 1 h in [bmim]Br (200 mg). After the reaction was completed, 10 mL of ethyl acetate was added to the reaction mixture and stirred for 15 min. The organic layer was separated, washed with water, and dried. The cycloadduct was further purified using hexane: ethyl acetate (3:2 v/v) as eluent employing column chromatography technique. After extraction of the cycloadduct, [bmim]Br wasdried under vacuum at 80 C for 2 h to exclude any water trapped from moisture and reused for subsequent runs.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-(Trifluoromethoxy)indoline-2,3-dione, and friends who are interested can also refer to it.

Reference:
Article; Kumar, Raju Suresh; Almansour, Abdulrahman I.; Arumugam, Natarajan; Mohammad, Faruq; Kotresha; Menendez, J. Carlos; Bioorganic and Medicinal Chemistry; vol. 27; 12; (2019); p. 2487 – 2498;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 897957-06-1, A common heterocyclic compound, 897957-06-1, name is 6-Bromo-1-methylindolin-2-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.

To a solution of 6-bromo-1-methyl-1 ,3-diotahydro-iotandol-2-one (226 mg, 1 0 mmol) in DMF (6 0 mL) was added zinc cyanide (117 mg 1 ,0 mmol). Then the reaction mixture was degassed and placed under an argon atmosphere and tetrakiotas(triotaphenylphosphiotane)palladiotaum(0) (115 mg, 0 1 mmol) was added The reaction was then placed at 95 C for 100 minutes, at which time it was cooled to room temperature, and diluted with saturated aqueous sodium bicarbonate and dichloromethane The layers were separated and the aqueous layer was extracted two additional times with dichloromethane The organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated The resulting residue was purified by silica gel flash chromatography (ethanol-dichloromethane 0 to 4%) to furnish 1- methyl-2-oxo-2,3-diotahydro-1 H-iotandole-6-carboniotatnle, MS. (ES+) m/z 173 0 (M+H)*

The synthetic route of 897957-06-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; ADAMS, Christopher Michael; CHAMOIN, Sylvie; HU, Qi-Ying; ZHANG, Chun; WO2010/130794; (2010); A1;,
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These common heterocyclic compound, 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-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. Quality Control of 6-Chloro-5-(2-chloroethyl)indolin-2-one

Example 1: Preparation of ziprasidone base To de-ionized water (2.0 Lit), was added 5- (2-chloroethyl)-6-chloro-oxindole (100 g) and 1- (1, 2-benzisothiazol-3-yl) piperazine (210 g) at 30-35C. The mixture was slowly heated under stirring to 98-100C over 60-80 minutes. The resultant mass was stirred for 10-15 hours at 98-100C. After completion of reaction as monitored by HPLC, the suspended solid material was filtered at 98-100C. The wet cake so obtained was suspended in de-ionized water (2.0 Lit) and heated to 90-95C and maintained at this temperature for 30 minutes. The solid suspension was filtered at 90-95C. The wet cake was further added to isopropyl alcohol (1.5 Lit) and stirred for 2 hours at 30-35C. The solids were filtered and washed with isopropyl alcohol (500 ml) and dried under vacuum at 50-55C for 7-8 hours till moisture content was not more than 1.0% w/w.; Example 7: Preparation of ziprasidone base To de-ionized water (4.0 Lit), was added 5- (2-chloroethyl)-6-chloro-oxindole (200 g) and 1- (1, 2-benzisothiazol-3-yl) piperazine (419.8 g) at 30-35C. The mixture was slowly heated under stirring to 98-100C over 60-90 minutes. The resultant mass was stirred for 12-15 hours at 98-100C. After completion of reaction as monitored by HPLC, the suspended solid material was filtered at 98-100C. The wet cake so obtained was suspended in de-ionized water (4.0 Lit) and heated to 90-95C and further maintained at this temperature for 30 minutes. The solid suspension was filtered at 90-95C. The wet cake was further added to isopropyl alcohol (3.0 Lit) and the resultant mass was heated to reflux and maintained at reflux for 1 hour. The mass was further cooled to 30-35C and stirred for 1 hour at 30-35C. The solids were filtered and washed with isopropyl alcohol (1.0 Lit) and dried under vacuum at 50-55C for 10-12 hours till moisture content was not more than 1.0% w/w. The product so obtained was suspended in tetrahydrofuran (7.3 Lit) and de-ionized water (580 ml) and heated to reflux (65-67C). The resultant mass was maintained under reflux for 10-15 minutes at 65-67C and further stirred under reflux at 65-67C for 40-45 minutes to get a clear solution. Activated carbon (29 g) was added to the clear solution at 65-67C with stirring for 1 hour at 65-67C. The reaction mass was filtered while hot under vacuum through celite bed at 65-67C. The celite bed was washed with tetrahydrofuran (580 ml). The solvent was recovered under vacuum at 50-55C leaving behind about 2.2 Lit of the reaction mass. The resultant suspension was cooled under stirring slowly to 35C and maintained for further 30 minutes. It was further cooled to 3- 5C and maintained for 2 hours under stirring at 3-5C. The solid separated was filtered and the wet cake was slurry washed with isopropyl alcohol (870 ml). The product was then dried under vacuum at 50-55C for 7-8 hours till the moisture was less than 0.5 % w/w. Yield : 267 g (68%) Purity: 99.96% by HPLC Impurity : Single known or unknown impurity 0.03% by HPLC

The synthetic route of 6-Chloro-5-(2-chloroethyl)indolin-2-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RANBAXY LABORATORIES LIMITED; WO2005/85240; (2005); A2;,
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Reference of 118289-55-7,Some common heterocyclic compound, 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-one, molecular formula is C10H9Cl2NO, 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. Preparation of ZPR in water containing 10% n-BuOH. In a three necked flask was charged BITP HCl (4. 9g), Na2C03 (6.91g), CEI (4.68g), water (25ml) and n-BuOH (2. 5ml), and the mixture was heated. After about 20 hours reflux, ziprasidone was 75.5% area from the reaction mixture, and after 35h reflux the conversion to ZPR was 88%. The solid was filtrated from the reaction mixture, washed with water and dried. The HPLC purity of the product was 93.6% area.

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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Synthetic Route of 118289-55-7, These common heterocyclic compound, 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-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.

Charged 5- (2-chloroethyl)-6-chloro oxindole (50 GM), 3- (1-PIPERAZINYL)- 1, 2-BENZISOTHIAZOLE (47.5 gm) and cyclohexane (500 mL) into an autoclave. To this sodium carbonate (46 GM), sodium iodide (3.2 GM), tetra butyl phosphonium bromide (14.8 gm) was added and the reaction was maintained at a temperature OF 95-102C and the pressure was kept at 2.5 KG/CM2 TILL the reaction was completed. The reaction mass was cooled to 30C and water (250 mL) was added. The resulting compound was filtered and washed with water (100 mL). The wet compound was further slurred in water (500 mL), filtered and washed with water (100 mL). To the water wet compound was added acetone (500 mL) and was stirred at room temperature for 2 hours and 30 minutes. The solid was filtered, washed with acetone (100 mL) and dried at a TEMPERATURE OF 60-65C to afford the Ziprasidone base (65.7 gm).

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

Reference:
Patent; DR. REDDY’S LABORATORIES LIMITED; DR. REDDY’S LABORATORIES INC.; WO2004/50655; (2004); A1;,
Indoline – Wikipedia,
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