Tag: M.W=200-300

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. 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Formula: C9H6BrNO2

General procedure: The benzofused N-heteroaromatic alkynes 2, 5, and 8 weresynthesized by reacting benzimidazole (1.0 mmol),benzotriazole (1.0 mmol), or carbazole (1.0 mmol) withpropargyl bromide (1.2 mmol) in the presence of potassiumcarbonate (2.0 mmol) using dimethylformamide bycontinuous stirring at 10-25 C up to 8-10 h [32]. For thesynthesis of target compounds, solution of aromatic bromides(1.0 mmol) in dimethylformamide was taken in around-bottomed flask and aqueous solution of sodium azide(3.0 mmol) was added, thereafter, stirred the reactionmixture for 1 h at 25-40 C. To the above reaction mixture,benzofused N-heteroaromatic alkyne 2 (1.0 mmol), 5(1.0 mmol), or 8 (1.0 mmol) was added followed by coppersulfate pentahydrate (5 mol %) and sodium ascorbate(10 mol %) [33], then, stirred the reaction contents overnight.The progress of reaction was monitored by thin layerchromatography. After the completion of reaction, ice-colddistilled water was added to the reaction mixture andproduct was extracted with ethyl acetate (50 cm3 9 3).The organic layer was washed with aqueous ammoniasolution followed by brine solution and dried using anhydroussodium sulfate. Filtered and evaporated the solventunder vacuum to get crude product which was furtherpurified by column chromatography using hexane:ethylacetate (7:3) as eluent.

According to the analysis of related databases, 5332-26-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kaushik; Kumar, Krishan; Lal, Kashmiri; Narasimhan, Balasubramanian; Kumar, Ashwani; Monatshefte fur Chemie; vol. 147; 4; (2016); p. 817 – 828;,
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Electric Literature of 90725-50-1, 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. 90725-50-1, name is 6-Bromo-3-methylindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

The compound [78-1] obtained in the process (1) (4.9 g) was suspended in toluene (22 mL), and borane dimethyl sulfide complex (4.4 mL) was added at 0C, and then the reaction mixture was heated at reflux for 2 hours. The reaction mixture was cooled with ice-water bath, and an aqueous solution of 5N-sodium hydroxide (8 mL), an aqueous solution of 8N-sodium hydroxide (8 mL) and ethyl acetate (8 mL) were added, successively, and then the reaction mixture was stirred at room temperature for 2.5 hours. The reaction mixture was quenched with water, and extracted with ethyl acetate. The obtained organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The residue was dissolved in tetrahydrofuran (100 mL), and triethylamine (4.55 mL) and a solution of di-tert-butyl dicarbonate (6.2 g) in tetrahydrofuran (10 mL) were added successively at room temperature, and then a grain of dimethylaminopyridine was added, and the reaction mixture was stirred at room temperature for 22 hours. The reaction mixture was quenched with water, and extracted with ethyl acetate. The obtained organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the titled compound (4.6 g) as a colorless oil. 1H-NMR (400 MHz, CDCl3) delta: 8. 03 (1H, s), 7. 07 (1H, dd, J = 7.9, 1.6 Hz), 6.96 (1H, d, J = 8.3Hz), 4.19-4.08 (1H, m), 3.57-3.43 (1H, m), 3.39-3.27 (1H, m), 1.53 (9H, brs), 1.30 (3H, d, J = 6.8 Hz). ESI-MS found: 256 [M-tBu+H]+

The synthetic route of 6-Bromo-3-methylindolin-2-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sato Pharmaceutical Co., Ltd.; NAGAI Keita; NAGASAWA Koh; TAKAHASHI Hirobumi; BABA Motoaki; FUJIOKA Shinichi; KONDOH Eri; TANAKA Kenichi; ITOH Yoshiki; EP2669270; (2013); A1;,
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Adding a certain compound to certain chemical reactions, such as: 18711-15-4, name is 4,6-Dichloroisatin, 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 18711-15-4, HPLC of Formula: C8H3Cl2NO2

General procedure: A solution of 4,6-dichloroisatine (7.2 g, 33 mmol) in THF (120 ml) was dropwise added under nitrogen atmosphere to 3,4-dichlorophenylmagnesium bromide (200 ml, 0.5 M in THF). The mixture was stirred 4 h at 70 C, then NH4Claq was added. After extraction in EtOAc, the organic phase was washed three times with NaOH 1 N, then dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel (cyclohexane/EtOAc = 8/2) to give 11 (6.73 g, 56%) as a white solid.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Puleo, Letizia; Marini, Pietro; Avallone, Roberta; Zanchet, Marco; Bandiera, Silvio; Baroni, Marco; Croci, Tiziano; Bioorganic and Medicinal Chemistry; vol. 20; 18; (2012); p. 5623 – 5636;,
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Adding a certain compound to certain chemical reactions, such as: 3783-77-5, name is 2-(3-Oxobutyl)isoindoline-1,3-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 3783-77-5, SDS of cas: 3783-77-5

b. 1-Bromo-4-phthalimidobutan-2-one (10a) To a suspension of 130 g (0.6 mole) of 4-phthalimido butan-2-one (7a) in 1000 ml of absolute methanol is added 96 g (0.6 mole) of bromine and the reaction mixture is stirred for 24 hours at room temperature. The precipitate, N-(4-bromo-3.3-dimethoxybutyl) phthalimide (8a) is filtered off, suspended in methanol and 30 ml of 10N sulfuric acid is added, after which the reaction mixture is heated until a clear solution is obtained. After cooling down the precipitate is collected and recrystallized from hot methanol. Yield 60%. Melting point: 120-122 C. (lit: R. G. Jones et al., J. Am. Chem. Soc., 72, 4526-4529 (1950), 119-120 C.). 1 H-NMR (CDCl3): 3.13 ppm., triplet, 2H (J=7.2 Hz); 3.92 ppm.,. singlet, 2H; 4.04 ppm., triplet (J=7.2 Hz), 2H; 7.60-7.96 ppm., multiplet, 4H.

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

Reference:
Patent; Cedona Pharmaceuticals B.V.; US5190589; (1993); A;,
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Indoline | C8H9N – PubChem

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. 4403-36-5, name is 2-(1,3-Dioxoisoindolin-2-yl)ethanesulfonylchloride, A new synthetic method of this compound is introduced below., Recommanded Product: 4403-36-5

To bis(4-methoxybenzyl)amine (Example 406.01, 3.37g, 13.10 mmol) and TEA (5.46 mL, 39.3 mmol) in DCM (109 mL) at 0 C was added 2-phthalimidoethanesulfonyl chloride (3.94 g, 14.41 mmol, commercially available from Matrix Scientific) slowly. The reaction was stirred at RT until complete by LCMS analysis. The reaction was diluted with a saturated solution of NaCl and extracted with DCM, dried over MgSO4, filtered and concentrated in vacuo. Purification of the residue by flash chromatography on a Versapak Spherical pre-packed silica gel column (Sigma-Aldrich, St. Louis, MO, eluent: 10-55% EtOAc/hexanes, gradient elution) provided Example 95.1 (4.04g, 62%) as a white solid after evaporation. The product was used directly in the next step without further purification.

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; AMGEN INC.; CHEN, Ning; CHEN, Xiaoqi; CHEN, Yinhong; CHENG, Alan C.; CONNORS, Richard V.; DEIGNAN, Jeffrey; DRANSFIELD, Paul John; DU, Xiaohui; FU, Zice; HARVEY, James S.; HEATH, Julie Anne; HEUMANN, Lars V.; HORNE, Daniel B.; HOUZE, Jonathan; KALLER, Matthew R.; KAYSER, Frank; KHAKOO, Aarif Yusuf; KOPECKY, David J.; LAI, Su-Jen; MA, Zhihua; MEDINA, Julio C.; MIHALIC, Jeffrey T.; NISHIMURA, Nobuko; OLSON, Steven H.; PATTAROPONG, Vatee; SWAMINATH, Gayathri; WANG, Xiaodong; WANSKA, Malgorzata; YANG, Kevin; YEH, Wen-Chen; (700 pag.)WO2018/97945; (2018); A1;,
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These common heterocyclic compound, 20780-72-7, name is 4-Bromoisatin, 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. Product Details of 20780-72-7

General procedure: A solution of 2-nitrobenzamides 1 or bis(2-nitrobenzamides) 4 (1 mmol), isatins 2 or acenaphthylene-1,2-diones 6 (1 mmol), and SnCl2*2H2O (4 mmol) in EtOH (5 mL) was stirred at reflux for 3-5 h. After this period, the TLC analysis of the mixture showed the reaction to be completed. The mixture was quenched with 3percent HCl (10 mL) and filtered to yield a crude product, which was purified by recrystallization from 95percent ethanol and DMF.

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

Reference:
Article; Hu, Yu; Wang, Man-Man; Chen, Hui; Shi, Da-Qing; Tetrahedron; vol. 67; 48; (2011); p. 9342 – 9346;,
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Electric Literature of 883-44-3,Some common heterocyclic compound, 883-44-3, name is 2-(3-Hydroxypropyl)isoindoline-1,3-dione, molecular formula is C11H11NO3, 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.

Dissolve 2- (3-HYDROXYPROPYL) ISOINDOLE-1, 3-dione (2 g, 9.74 mmol, leq) in 40 mL of dichloromethane under N2. Add sulfuric acid (780 U. L) and cool reaction mixture to – 5C. Condense isobutylene gas to a liquid using a-78C cold finger charged with dry ice and acetone. Add approximately 20 mL of the condensed liquid to the reaction mixture and slowly warm the solution to room temperature overnight while stirring. Add saturated, aqueous sodium hydrogencarbonate to the reaction mixture and extract product into the organics. Wash separated organic layer with water and dry over magnesium sulfate to give 1.969 g (77% yield) of 2- (3-TERT-BUTOXYPROPYL) ISOINDOLE-1, 3-dione as a colorless oil.

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

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/9941; (2005); A1;,
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Indoline | C8H9N – PubChem

Related Products of 118289-55-7, 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. 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-one, This compound has unique chemical properties. The synthetic route is as follows.

1 mole of Piperazine Benzisothiazole hydrochloride, 1 mole of 5-(2-chloroethyl)- 6-chlorooxindole, 3.3 mole of Sodium carbonate, water 5.2 times based on oxindole weight and 1 % of dispersing agent Morwet D425 are charged in to the flask and refluxed under nitrogen, under stirring for 12-16hr. After the completion of the reaction, the reaction mass is cooled to room temperature and the resulting mass is filtered. It is slurried in water and then in IPA and isolated by filtration. The solid is dried at 95-1000C.Yield: 90 %; Purity: 100.30%

The chemical industry reduces the impact on the environment during synthesis 6-Chloro-5-(2-chloroethyl)indolin-2-one. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ALKEM LABORATORIES LTD.; WO2009/116085; (2009); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 18711-15-4, name is 4,6-Dichloroisatin, A new synthetic method of this compound is introduced below., name: 4,6-Dichloroisatin

Accurately weighed 4,6-dichloro isatin (0.56 g),Sarcosine (0.25 g)Was added to a 100 mL flask,Add about 50mL ethanol solvent,Dropwise pulegone (0.3 g).The reaction was carried out under conditions catalyzed by phosphotungstic acid (0.5 g), heated to 80 C with a heat jacket,Placed on a magnetic stirrer,Reflux reaction for 6 hours,The reaction solution was concentrated by rotary steam and then filtered,The obtained filter cake was recrystallized by adding 50 ml of a mixed solution of ethyl acetate and petroleum ether 1: 1,A pale yellow crystalline powder (0.57 g)The overall yield was 72.6%.

The synthetic route of 18711-15-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shaanxi University of Science and Technology; Liang, Chengyuan; Song, Huihui; Chang, Xiangna; (15 pag.)CN104193749; (2017); B;,
Indoline – Wikipedia,
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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. 132898-96-5, name is 2,3-Dioxoindoline-5-sulfonyl chloride belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 2,3-Dioxoindoline-5-sulfonyl chloride

(S)-5-(2-(4-Fluorophenoxymethyl)-pyrrolidine-1-sulfonyl)isatin (compound 20b). To a stirred solution of 19b (0.15 g, 0.5 mmol) in dry DCM (4 mL) cooled in an ice bath was added TFA (0.6 mL, 10 mmol). After 1 h bulk solvent was removed in vacuo and the residue remaining taken up in dry DCM (8 mL) and cooled in an ice bath. Dry triethylamine (1.5 mL) was then added followed by 5-chlorosulfonylisatin8 (0.16 g, 0.65 mmol) in dry THF (4 mL) and the solution was then stirred. After 19 h bulk solvent was removed in vacuo and redissolved in DCM (10 mL), washed with water (2*10 mL), then brine (1*10 mL) and dried over Na2SO4. Chromatography (hexanes/ethyl acetate) gave the desired product as an orange solid (104 mg, 51%). Mp: 205-207 C. HRMS (ESI)=405.0941 (M+H)+. Calcd. for C19H18FN2O5S 405.0920. 1H NMR (600 MHz, CDCl3) delta 8.10 (s, 1H), 8.08 (dd, J=8.4 Hz, J=1.8 Hz, 1H), 8.00 (br, 1H), 7.00 (d, J=7.8 Hz, 1H), 6.99-6.95 (m, 2H), 6.83-6.81 (m, 2H), 4.17 (dd, J=9.6 Hz, J=3.6 Hz, 1H), 3.98-3.95 (m, 1H), 3.91 (dd, J=9 Hz, J=7.8 Hz, 1H), 3.54-3.50 (m, 1H), 3.24-3.19 (m, 1H), 2.10-1.99 (m, 2H), 1.87-1.77 (m, 2H). TLC (UV254) Rf=0.27 (2:1 ethyl acetate/hexanes). HPLC tR=7.83

The synthetic route of 132898-96-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Imperial Innovations Limited; Hammersmith Imanet Limited; US2011/195024; (2011); A1;,
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