Tag: M.W=200-300

Related Products of 20870-78-4, The chemical industry reduces the impact on the environment during synthesis 20870-78-4, name is 5-Bromoindolin-2-one, I believe this compound will play a more active role in future production and life.

Reference Example 27 Production of (Z)-5-((5-bromo-2-oxoindolin-3-ylidene)methyl)-N-(2-(diethylamino)ethyl)-2,4-dimethyl-1H-pyrrole-3-carboxamide To the solution of 5-bromoindolin-2-one (262 mg, 1.24 mmol) in EtOH (5 ml) was added N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide (298 mg, 1.12 mmol) and piperidine (112 muL, 1.13 mmol). The mixture was stirred at 80 C. for 1 hour. After cooled down to room temperature, the reaction mixture was concentrated, filtrated, and washed with EtOH to give (Z)-5-((5-bromo-2-oxoindolin-3-ylidene)methyl)-N-(2-(diethylamino)ethyl)-2,4-dimethyl-1H-pyrrole-3-carboxamide (368 mg) as orange solid. MS m/z 459.4/461.4 (M+H)

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-Bromoindolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Tsuboi, Katsunori; Takanashi, Yosuke; Tojo, Shingo; Kodama, Tomohiro; Kubota, Katsumi; Kanai, Toshio; US2014/275076; (2014); A1;,
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Related Products of 954-81-4,Some common heterocyclic compound, 954-81-4, name is N-(5-Bromopentyl)phthalimide, molecular formula is C13H14BrNO2, 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: For the synthesis of compounds 6a-d we used commercially available (from Sigma Aldrich) N-(bromoalkyl)isoindoline-1,3-diones. To the solution of N-(bromoethyl)isoindoline-1,3-dione (3.93 mmol) in DMF, sodium azide (11.79 mmol) was added and the contents were heated at 80 C for 6-8 h. After completion, reaction mixture was quenched with ice water and extracted with DCM thrice. The organic extracts were combined, dried over anhydrous sodium suphate, filtered, and concentrated under reduced pressure to give corresponding products as colorless oil and was used without further purification

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route N-(5-Bromopentyl)phthalimide, its application will become more common.

Reference:
Article; Kushwaha, Khushbu; Kaushik, Nagendra; Lata; Jain, Subhash C.; Bioorganic and Medicinal Chemistry Letters; vol. 24; 7; (2014); p. 1795 – 1801;,
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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. 65435-04-3, name is 5-(2-Chloroacetyl)indolin-2-one, A new synthetic method of this compound is introduced below., HPLC of Formula: C10H8ClNO2

A suspension of 9.3 g of 5-chloroacetyl-2-oxindole was stirred in 90 mL pyridine at 80 to 90 C. for 3 hours then cooled to room temperature. The precipitate was collected by vacuum filtration and washed with 20 mL ethanol. The solid was dissolved in 90 mL 2.5N sodium hydroxide and stirred at 70 to 80 C. for 3 hours. The mixture was cooled to room temperature and acidified to pH 2 with 0.5 N hydrochloric acid. The precipitate was collected by vacuum filtration and washed thoroughly with water to give crude 5-carboxy-2-oxindole as a dark brown solid.

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; Sugen, Inc.; US6486185; (2002); B1;; ; Patent; Sugen, Inc.; US6114371; (2000); A;,
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Application of 2058-72-2, These common heterocyclic compound, 2058-72-2, name is 5-Bromo-1-methylindoline-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 isatin derivatives 1 (1 mmol), 1-aryl-2-thiocyanatoethanone 2 (1 mmol) and Et3N (1mmol) in EtOAc (3 mL) was stirred at room temperature for 8 h. Then hydrazonoyl chloride 3 (1mmol) was added to the above mixture and the reaction was stirred at reflux temperature for 10min. After completion of the reaction, the reaction mixture was filtered, EtOAc was evaporated andthe residue was purified by recrystallization from ethanol to afford the pure product 4 in high yield.The two disterioisomers of products 4a-c were separated by washing the precipitate with n-Hexane/EtOAc (10/1)

Statistics shows that 5-Bromo-1-methylindoline-2,3-dione is playing an increasingly important role. we look forward to future research findings about 2058-72-2.

Reference:
Article; Alizadeh, Abdolali; Moafi, Leila; Synlett; vol. 27; 12; (2016); p. 1828 – 1831;,
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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 261732-38-1 as follows. Application In Synthesis of tert-Butyl 5-bromoindoline-1-carboxylate

A solution of the title B compound, 5-bromo-2, 3-DIHYDRO-INDOLE-1-CARBOXYLIC acid tert-butyl ester (15.86 g, 53.22 mmol) in 500 mL THF is cooled TO-73C and treated with n-butyllithium (1.6 M in hexanes, 53.22 mL, 85.15 MMOL). After 15 min AT-73C, dry COs is bubbled through the solution for 40 min. The reaction is kept AT-73C for 1 h, warmed to 0C for 1 h, and then warmed to RT for 1 h. The mixture is poured into 1 N aqueous HCI and extracted twice with diethyl ether. The diethyl ether layers are combined, washed with brine, dried over anhydrous MGS04, and concentrated to afford of 2, 3-dihydro-indole-1, 5-dicarboxylic acid 1-tert-butyl ester as an white solid : NMR (DMSO-D6) 1.51 (s, 9H), 3.10 (t, 2H, J = 8.75), 3. 69 (t, 2H, J = 8.80), 7.73-7. 79 (m, 3 H), 12.62 (br s, 1 H).

According to the analysis of related databases, 261732-38-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2004/65351; (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.

To a flask equipped with mechanical stirrer, thermometer, condenser and nitrogen inlet was added 6-chloro-5-(2-chloroethyl)-l,3-dihydro-2H-indol-2- one (21.6 g, 94 mmol), 3-(l-piperazinyl)-l,2-benzoisothiazole hydrochloride (24 g, 94 mmol), sodium carbonate (29.9 g, 282 mmol) and l-methyl-2- pyrrolidinone (NMP) (96 ml) and the mixture was heated to 130-1350C under nitrogen for about 24 hrs. The mixture was cooled to 40-450C and poured into water. The suspension was cooled and the product was collected by filtration on a Buchner funnel, the filter cake was rinsed with water at 20- 250C and the damp product was transferred to a drying oven and dried in vacuo. This afforded 34.2 g (88.2% yield) of crude ziprasidone. The IR (KBr) and NMR spectra were consistent with those of reference ziprasidone.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Chloro-5-(2-chloroethyl)indolin-2-one, its application will become more common.

Reference:
Patent; APOTEX PHARMACHEM INC.; WO2006/47893; (2006); A1;,
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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. Application In Synthesis of N-(5-Bromopentyl)phthalimide

General procedure: Compound 5 (5.67g, 12mmol) was added into MeCN (50mL), and then Compound 6-9 (14.2mmol) were added, respectively. After an addition of K2CO3 (5.9g, 42.6mmol), the mixture was refluxed for 24h and followed by TLC. After the solvent was removed by distillation under reduced pressure, the residue was dissolved in EtOAc (200mL), and washed by water (3¡Á50mL). The organic phase was dried by MgSO4, and then was evaporated. The crude product was purified by column chromatography (DCM/EtOAc=20:1, Rf=0.7) to give 10-13 as white solid.

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

Reference:
Article; Duan, Xiaojiang; Ruan, Qing; Gan, Qianqian; Song, Xiaoqing; Fang, Si’an; Zhang, Xuran; Zhang, Junbo; Journal of Organometallic Chemistry; vol. 868; (2018); p. 154 – 163;,
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Synthetic Route 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.

Under nitrogen atmosphere, 70 mg of 5-bromo-1-oxo-isoindoline was dissolved in 2 ml of tetrahydrofuran, cooled down to 0C, and then 4 mg of N,N-dimethylaminopyridine and 144 mg of di-tert-butylcarbonate were added. The mixture was stirred at room temperature for 30 min. Methanol was added to the reaction solution, and the solvents were distilled outunder reduced pressure. Water was added to the residues, extracted with ethyl acetate. Ethyl acetate layer was washed with saturated saline solution, and dried with anhydrous sodium sulfate. After distilling out the solvents under reduced pressure, the residues were separated and purified by silicagel column chromatography (ethyl acetate/hexane=1/2), to obtain 51.2 mg of the above compound as a white solid. 1HNMR(400MHz,CDCl3.)delta.:1.60(9H,s), 4.74(2H,s), 7.62-7.65(2H,m), 7.76(1H,d,J=8.0Hz). 1) Manufacture of 5-bromo-2-tert-butoxycarbonyl-1-oxo-isoindoline Under nitrogen atmosphere, 1.5 mg of 5-bromo-1-oxo-isoindoline was dissolved in 20 ml of tetrahydrofuran, cooled down to 0C. Then, 85 mg of N,N-dimethylaminopyridine and 3.0 ml of tert-butylcarbonate were added, and the mixture was stirred at room temperature for 30 min. Methanol was added to the reaction solution, and the solvents were distilled outunder reduced pressure. Water was added to the residues, extracted with ethyl acetate. Ethyl acetate layer was washed with saturated saline solution, and dried with anhydrous sodium sulfate. After distilling out the solvents under reduced pressure, the residues were separated and purified by silicagel column chromatography (ethyl acetate/hexane=1/2), to obtain 300 mg of the above compound as a white solid. 1HNMR(400MHz,CDCl3.)delta.:1.60(9H,s), 4.74(2H,s), 7.62-7.65(2H,m), 7.76(1H,d,J=8.0Hz) ESI-MS Found:m/z 344.2[M+Na]+

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; BANYU PHARMACEUTICAL CO., LTD.; EP1726585; (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 5394-18-3 as follows. Safety of 2-(4-Bromobutyl)isoindoline-1,3-dione

General procedure: Amixture of the corresponding secondary amine 7a-d (5.5 mmol), anhydrous K2CO3 (6 mmol) andcompounds 2-4 (5 mmol) was added inCH3CN (20 ml). The mixture was heated at 65 C for 8-10 h. Thesolvent was evaporated under reduced pressure. Then water (25 mL) was added,and the mixture was extracted with dichloromethane (20 mL ¡Á 3). The combinedorganic phases were washed with saturated aqueous NaCl (30 mL), dried oversodium sulfate, and filtered. The solvent was evaporated under a vacuum. The residue was purified on a silicagel chromatography using mixtures of petroleum/acetone as eluent to obtain theoil products 8-10.

According to the analysis of related databases, 5394-18-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Pan, Wanli; Hu, Ke; Bai, Ping; Yu, Lintao; Ma, Qinge; Li, Tao; Zhang, Xu; Chen, Changzhong; Peng, Kelin; Liu, Wenmin; Sang, Zhipei; Bioorganic and Medicinal Chemistry Letters; vol. 26; 10; (2016); p. 2539 – 2543;,
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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 919103-45-0 as follows. Application In Synthesis of 6-Iodoindolin-2-one

Preparation 2: (2-Oxo-2,3-dihydro-1H-indol-6-ylsulfanyl)-benzoic acid CuI (40 mg, 0.05 mmol), potassium carbonate (1.66 g, 12 mmol), 6-iodooxindole (as prepared in Preparation 1; 1.0 g, 4.0 mmol) and 2-mercapto-benzoic acid (0.62 g, 4.0 mmol) were added to a dry schlenk tube. The tube was evacuated and refilled with Ar(g) (3 times). 2-Propanol (5.0 mL) and ethylene glycol (0.5 mL, 8.0 mmol) were injected into the schlenk tube. The schlenk tube was sealed with a teflon valve and was heated to 80 C. and stirred for over 24 hours. Subsequently the reaction mixture was allowed to reach room temperature then diluted with EtOAc (10 mL) and water (10 mL). The mixture was acidified of to a pH=3-4 with the addition of 1 M HCl(aq) and the organics were separated and set aside. The aqueous phase was washed with additional EtOAc (10 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo affording a yellow solid. The solid was then purified via flash silica gel chromatography (gradient eluant starting with 5% MeOH in CHCl3 increasing to 10% MeOH in CHCl3) affording the title compound as a pale yellow solid (0.228 g, 0.77 mmol, 20% yield).

According to the analysis of related databases, 919103-45-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Allergan, Inc.; US2007/15748; (2007); A1;,
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