Author: Jessica.F

Electric Literature of 675109-26-9, 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. 675109-26-9 name is 6-Bromoisoindolin-1-one, 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.

To a mixture of 6-bromoisoindolin-1-one (7.00 g, 3.30 mmol) and 1, 4-dioxane (125 mL), were added bis (pinacolato)diboron (17.00g, 6.60mmol), KOAc (8.50 g, 8.25 mmol) and Pd(dppf)Cl2 (2.50 g, 0.33 mmol). The reaction mixture was stirred at 90 oC for 12h under N2 atmosphere. After cooling to r. t. the reaction mixture was filtered. The solvent evaporated under reduced pressure then added ethyl acetate (80 mL). The precipitate was filtered to obtained black solid. Yield 70%, m.p. > 250oC. 1H NMR (300 MHz, CDCl3) delta (ppm): 8.36 (s, 1H, ArH), 8.00 (d, J = 7.60 Hz, 1H, ArH), 7.48 (d, J = 7.60 Hz, 1H, ArH), 7.03 (s, 1H, NH), 4.48 (s, 2H, CH2), 1.35 (s, 12H, CH3).

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

Reference:
Article; Ji, Dezhong; Zhang, Lingzhi; Zhu, Qihua; Bai, Ying; Wu, Yaoyao; Xu, Yungen; European Journal of Medicinal Chemistry; vol. 164; (2019); p. 334 – 341;,
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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;,
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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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Application of 611-09-6,Some common heterocyclic compound, 611-09-6, name is 5-Nitroindoline-2,3-dione, molecular formula is C8H4N2O4, 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.

Intermediate 2 (200mg, 1.04mmol), neopentyl glycol (108mg,1.04mmol) and p-toluenesulfonic acid (25mg, 145mumol) were suc-cessively added and dissolved in cyclohexane (10mL). The resulting reaction mixture was refluxed for 16 h at 85 C. After completion of the reaction, the mixture was cooled to room temperature. Then, the pre-cipitate was filtered ,washed with water and dried .Purification by chromatography on silica gel (petroleum ether/ethyl acetate=5/1)afforde dintermediate3.White solid; yield 84%; mp: 201-203C; 1 H NMR (400MHz,DMSO-d 6 ) delta 11.20 (s, 1H), 8.28 (dd, J=8.7, 2.4Hz, 1H), 8.08 (d,J=2.4Hz, 1H), 7.04 (d, J=8.7Hz, 1H), 4.49 (d, J=11.0Hz, 2H),3.55 (d, J=11.2Hz, 2H), 1.34 (s, 3H), 0.84 (s, 3H).

The synthetic route of 611-09-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yu, Shengping; Liu, Yang; Zhang, Zhen; Zhang, Jingya; Zhao, Guisen; Bioorganic and Medicinal Chemistry; vol. 27; 15; (2019); p. 3319 – 3327;,
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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 7477-63-6 as follows. Product Details of 7477-63-6

General procedure: A mixture of isatins 1 (1 mmol), substituted 1H-pyrazol-5-amine 2 (1 mmol), 6-aminopyrimidine-2,4(1H,3H)-dione 3 or 6-amino-1,3-dimethylpyrimidine-2,4(1H,3H)-dione 5 (1 mmol), H2O(6 mL), and HOAc (2 mL) was placed in a 25-mL flask andstirred at 90 ¡ãC (monitored by thin layer chromatography (TLC)) for about 7 h. Afterreaction completion, the mixture was cooled to room temperature and the precipitateobtained by filtration. Compounds 4 or 6 were further purified by recrystallizationfrom DMF.

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; Dai, Lei; Mao, Kaimin; Pan, Zhengbing; Rong, Liangce; Research on Chemical Intermediates; vol. 45; 2; (2019); p. 769 – 788;,
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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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These common heterocyclic compound, 2058-74-4, name is 1-Methylisatin, 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. Safety of 1-Methylisatin

A solution of N-methylisatin (322 mg, 2.0 mmol), phenylacetylene (306 mg, 3.0 mmol), CuI (76 mg, 0.4 mmol), and Cs2CO3 (978 mg, 3.0 mmol) in CH3CN (4.0 mL) was stirred at room temperature for 18 h. After aqueous extractive workup and column chromatographic purification process (CH2Cl2/EtOAc, 15:1) 1a was obtained as a pale yellow solid, 347 mg (66%). Other compounds were prepared similarly, and compounds 1a-1i are all known compounds.1

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

Reference:
Article; Roh, Hwa Jung; Kim, Gieun; Cho, Sung; Ryu, Ji Yeon; Lee, Junseong; Kim, Jae Nyoung; Tetrahedron Letters; vol. 59; 15; (2018); p. 1484 – 1488;,
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Electric Literature of 59-48-3, 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 59-48-3 as follows.

3-Methyl-1,3-dihydro-indol-2-one A solution of oxindole (665 mg, 5.0 mmol) in THF (10 ml) was treated dropwise with n-BuLi (4.4 ml, 11.0 mmol) at -78 C., stirred for 30 min. at -78 C. To the reaction methyliodine (2 ml) was added dropwise at -78 C. The resulting solution was warmed up to room temperature. The mixture was quenched with water. The reaction solution was partitioned between ethylacetate and water. The organic layer was washed (brine), dried (Na2SO4), filtered and concentrated under vacumm. Purification on silica gel with 30% ethyl acetate/hexane to provide the title compound (630 mg, 86%). MS (DCI/NH3) m/e 148 (M+1)+.

According to the analysis of related databases, 59-48-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Li, Qun; Woods, Keith W.; Zhu, Gui-Dong; Fischer, John P.; Gong, Jianchun; Li, Tongmei; Gandhi, Virajkumar; Thomas, Sheela A.; Packard, Garrick K.; Song, Xiaohong; Abrams, Jason N.; Diebold, Robert; Dinges, Jurgen; Hutchins, Charles; Stoll, Vincent S.; Rosenberg, Saul H.; Giranda, Vincent L.; US2003/187026; (2003); A1;,
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Electric Literature of 16800-68-3, These common heterocyclic compound, 16800-68-3, name is 1-Acetylindolin-3-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.

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.

The synthetic route of 16800-68-3 has been constantly updated, and we look forward to future research findings.

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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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. 2058-74-4, name is 1-Methylisatin, A new synthetic method of this compound is introduced below., Product Details of 2058-74-4

General procedure: To a magnetically stirred mixture of isatins (1 mmol) and IL I (12.6 mg, 0.05 mmol) were added alkyl-malonates (1 mmol) or 1,3-dicarbonyl compounds (1 mmol) and then the reaction mixture was stirred at room temperature . After completion of the reaction (monitored by TLC), EtOAc was added to the reaction mixture, and [TBD][TFA] was removed by filtration and washed with EtOAc (2 5 ml).The filtrate was evaporated under reduced pressure to give the solid product as a residue in almost pure form. If necessary, the product could further be purified byrecrystallization from ethanol.

The synthetic route of 2058-74-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Baghbanian, Seyed Meysam; Tajbakhsh, Mahmood; Farhang, Maryam; Comptes Rendus Chimie; vol. 17; 12; (2014); p. 1160 – 1164;,
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