Author: tianli

Reference of 675109-26-9, These common heterocyclic compound, 675109-26-9, name is 6-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.

Preparation 124: Methyl 3-(6-bromo-1 -oxo-2,3-dihydro-1 H-isoindol-2-yl)propanoate (1728) To a stirred solution of 6-bromo-2,3-dihydro-1 H-isoindol-1-one (550 mg, 2.59 mmol), 18-crown-6 (69 mg, 0.26 mmol) and methyl 3-bromopropionate (350 pL, 3.1 1 mmol) in DMF (9 ml.) was added CS2CO3 (2.113 g, 6.48 mmol) under nitrogen. The reaction was heated to 70 C (1729) (thermally) slowly and maintained at this temperature for 18 hours. After cooling and the reaction was quenched with NH4CI (sat., aq.). The mixture was extracted with EtOAc (x3) and the combined organic layers were washed with brine, dried over MgSO, filtered and (1730) concentrated under vacuum to yield methyl 3-(6-bromo-1-oxo-2,3-dihydro-1 H-isoindol-2- yl)propanoate as a yellow oil. LC-MS was consistent with a complex mixture which was taken on as is. To the residue was added bis(pinacolato)diboron (0.746 g, 2.91 mmol), AcOK (0.491 mg, 5.00 mmol) and anhydrous 1 ,4-dioxane (8 ml_). The reaction was degassed with nitrogen for 5 minutes. 1 ,1 ‘-Bis(diphenylphosphino)ferrocene-palladium(ll)dichloride dichloromethane complex (61 mg, 0.08 mmol) was then added and the reaction heated at 90C under nitrogen for 16 hours. The reaction was allowed to cool to room temperature and was then diluted with water. The mixture was extracted with EtOAc (x3) and the combined organic layers were washed with brine, dried over MgSO, filtered and concentrated under vacuum to yield the title compound (1.5 g, 168 %) which was used without further purification. MS: [M+H]+ = 346.

The synthetic route of 675109-26-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; BERDINI, Valerio; BUCK, Ildiko Maria; DAY, James Edward Harvey; GRIFFITHS-JONES, Charlotte Mary; HEIGHTMAN, Thomas Daniel; HOWARD, Steven; MURRAY, Christopher William; NORTON, David; O’REILLY, Marc; WOOLFORD, Alison Jo-Anne; COOKE, Michael Liam; COUSIN, David; ONIONS, Stuart Thomas; SHANNON, Jonathan Martin; WATTS, John Paul; (867 pag.)WO2017/68412; (2017); 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 959235-95-1 as follows. name: 6-(Trifluoromethoxy)indoline

A mixture of 6-(trifluoromethoxy)indoline [CAS 959235-95-1 ] (1 .2 g, 5.89 mmol), 2- (2-(2-(benzyloxy)ethoxy)-4-chlorophenyl)-2-((3-methoxy-5-(1 H-1 ,2,4-triazol-1 – yl)phenyl)amino)acetic acid 6d (2.5 g, 4.91 mmol), HATU (2.29 g, 6.01 mmol) and diisopropylethylamine (1 .99 ml_, 12.0 mmol) in DMF (18 ml_) was stirred at room temperature for 2 h. The mixture was diluted with water. The precipitate was filtered off and washed with water. The precipitate was taken up with EtOAc, washed with a solution of K2CO3 10% in water, water, dried over MgSO4, filtered and the solvent was concentrated under reduced pressure. The compound was purified by flash chromatography on silica gel (15-40 muiotatauiota, 220 g, heptane/EtOAc 50/50). The pure fractions were combined and the solvent was concentrated under reduced pressure to give 2-(2-(2-(benzyloxy)ethoxy)-4-chlorophenyl)-2-((3- methoxy-5-(1 H-1 ,2,4-triazol-1 -yl)phenyl)amino)-1 -(6-(trifluoromethoxy)indolin-1- yl)ethanone 6e (2.5 g).

According to the analysis of related databases, 959235-95-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICALS, INC.; KATHOLIEKE UNIVERSITEIT LEUVEN; KESTELEYN, Bart Rudolf Romanie; BONFANTI, Jean-Francois; COESEMANS, Erwin; RABOISSON, Pierre Jean-Marie Bernard; MARCHAND, Arnaud Didier M; BARDIOT, Dorothee Alice Marie-Eve; (92 pag.)WO2018/178240; (2018); A1;,
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Reference of 825-70-7, 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 825-70-7 as follows.

Step 2a:(R)-1-(5-Fluoro-2-methyl-2,3-dihydroindol-1-yl)-2-phenoxypropan-1-one: diastereoisomer A And(R)-1-(5-Fluoro-2-methyl-2,3-dihydroindol-1-yl)-2-phenoxypropan-1-one: diastereoisomer B 2.9 g of 5-Fluoro-2-methyl-2,3-dihydro-1H-indole and 5.3 g of N-[3-(dimethylamino)propyl]-N?-ethylcarbodiimide hydrochloride are added to a solution of 4.17 g of o-benzyl-D-lactic acid in 17 ml of DMF and 3.43 ml of pyridine.The reaction medium is stirred at ambient temperature for 18 hours.500 ml of ethyl acetate and 500 ml of water are added. After settling out, the organic phase is dried over magnesium sulfate, filtered, and then concentrated under reduced pressure. The residue obtained is purified on a silica cartridge: eluent: heptane, then 95/05 heptane/ethyl acetate, then 90/10 heptane/ethyl acetate, so as to give 2.8 g of (R)-1-(5-fluoro-2-methyl-2,3-dihydroindol-1-yl)-2-phenoxypropan-1-one: diastereoisomer A in the form of a yellow oil, the characteristics of which are the following:Mass spectrometry: method ARetention time Tr (min)=1.08;[M+H]+: m/z 314And 2.63 g of (R)-1-(5-fluoro-2-methyl-2,3-dihydroindol-1-yl)-2-phenoxpropan-1-one: diastereoisomer B in the form of a white solid, the characteristics of which are the following:Mass spectrometry: method ARetention time Tr (min)=1.06;[M+H]+: m/z 314; base peak: m/z 242

According to the analysis of related databases, 825-70-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SANOFI; Brollo, Maurice; Carry, Jean-Christophe; Certal, Victor; Didier, Eric; Doerflinger, Gilles; EL Ahmad, Youssef; Filoche-Romme, Bruno; Halley, Frank; Karlsson, Karl Andreas; Schio, Laurent; Thompson, Fabienne; US2013/274253; (2013); A1;,
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Related Products of 3891-07-4, 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 3891-07-4 as follows.

To a mechanically stirred suspension of NaH (15g, 0. 375 mol, 60% dispersion in mineral oil) in THF (250 mL) and DMF (25 mL) was added N- (2-hydroxyethyl)-phtalimide (43g, 0. 225 mol). The mixture was stirred at room temperature for about 4 h and then cooled to about 0C in an ice bath. Ethyl-4- chloroacetate (21. 4 mL, 0. 15 mol) in THF (4 mL) was then added via an addition funnel over a period of about 0. 5 h and the resulting mixture allowed to stir overnight. The mixture was then poured into a 2 L sepratory funnel containing 500 mL ice water and 700 mL EtOAc and separated. The organic layer was washed 2x with 500 mL of water and dried over MGS04. The solution was then filtered through a 4-inch plug of silica and then CONCENTRATED IN VACUO. The resulting yellow oil was then dissolved in 250 mL CH3CN and washed 2x with 30 mL hexane. The CH3CN layer was the concentrated in vacuo to yield 19. 4g (40. 5%) OF 4- [2- (1, 3-DIOXO-1, 3-DIHYDRO-ISOINDOL-2-YL)-ETHOXY]-3-OXO-BUTYRIC acid ethyl ester as a yellow oil. This crude compound was used for the next step

According to the analysis of related databases, 3891-07-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SYNTA PHAMACEUTICALS CORP.; WO2005/25507; (2005); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 13220-46-7, name is 4-Methylindolin-2-one, 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 13220-46-7, Recommanded Product: 13220-46-7

5-Chloro-4-methyl-2-oxindole A suspension of 3.0 g of 4-methyl-2-oxindole was stirred in 50 mL of acetonitrile at room temperature while 3.3 g of N-chlorosuccinimide was added in portions. Trifluoroacetic acid (1 mL) was then added. The suspension was stirred at room temperature for 3 days during which time solid was always present. The white solid was collected by vacuum filtration, washed with a small amount of cold acetone and dried overnight in a vacuum oven at 40 C. to give 2.5 g (68%) of 5-chloro-4-methyl-2-oxindole.

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:
Patent; Sugen, Inc.; US6051593; (2000); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 20780-72-7, 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. 20780-72-7 name is 4-Bromoisatin, 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.

General procedure: A reaction flask with high vacuum valve was charged with 2-amino-N?-arylbenzohydrazides (1.0 mmol), 4-halogenated isatins (1.0 mmol), CuI (10 mg, 0.05 mmol), and Cs2CO3 (650 mg, 2.0 mmol). After being degassed by three freeze-thaw pump cycles, THF (10.0 mL) was injected into the mixture. And then, the reaction mixture was stirred at reflux for 10?16 h before reaching completion, which was monitored by TLC. The solvent was recovered by distillation under reduced pressure, and the residue was purified by chromatography over silica gel to give 3 using ethyl acetate and petroleum ether (1:2) as an eluent.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromoisatin, and friends who are interested can also refer to it.

Reference:
Article; Ma, Yong-Gang; Li, Chao; Yao, Chang-Sheng; Wang, Xiang-Shan; Tetrahedron; vol. 72; 27-28; (2016); p. 3844 – 3850;,
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Synthetic Route of 2058-72-2, A common heterocyclic compound, 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, molecular formula is C9H6BrNO2, 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.

The key intermediate 2 was refluxed with equivalent amount ofdifferent isatin derivatives 4a-f or 8a-l in glacial acetic acid. Thereaction was monitored with TLC. After complete of the reaction,the formed solid was collected and washed with water andrecrystallized from DMF/ethanol to get the target compounds 6a-fand 9a-l respectively.

The synthetic route of 2058-72-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Eldehna, Wagdy M.; Abo-Ashour, Mahmoud F.; Nocentini, Alessio; El-Haggar, Radwan S.; Bua, Silvia; Bonardi, Alessandro; Al-Rashood, Sara T.; Hassan, Ghada S.; Gratteri, Paola; Abdel-Aziz, Hatem A.; Supuran, Claudiu T.; European Journal of Medicinal Chemistry; vol. 162; (2019); p. 147 – 160;,
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Indoline | C8H9N – PubChem

Related Products of 18711-13-2, 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. 18711-13-2, name is 4,7-Dichloroindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of DHEA (0.5 mmol, 1.0 eq) and isatin derivative(0.75 mmol, 1.5 eq) in EtOH (10 mL) was added Al2O3/KF (0.5 mmol,1.0 eq), the resulting mixture was stirred at reflux temperature for 6 h.Upon completion of the reaction indicated by the TLC, the mixture wasfiltered and the solid was washed with dichloromethane (DCM) forseveral times. The filtrate was then evaporated under vacuum, followedby addition of DCM and H2O. The mixture was then acidified with 4MHCl (pH=1-2). The aqueous layer was washed with DCM for severaltimes. The combined organic layers were then dried over Na2SO4 andevaporated under vacuum to the crude product, which was then subjectedto column chromatography, affording the corresponding product.

The chemical industry reduces the impact on the environment during synthesis 4,7-Dichloroindoline-2,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Article; Yang, Yan-Tao; Du, Shuzhang; Wang, Song; Jia, Xuedong; Wang, Xiaojuan; Zhang, Xiaojian; Steroids; vol. 151; (2019);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 102359-00-2, A common heterocyclic compound, 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, molecular formula is C9H7NO3, 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.

A mixture of 2-oxoindoline-5-carboxilic acid (5.221 g, 29.50 mmol) and triethylorthobenzoate (20.16 g, 90 mmol)in acetic anhydride (75 ml) were stirred at 100 C for 8 h.The solvent was removed under reduced pressure. The residuewas stirred with i-Pr2O (250 ml) for 2 h to give a solid which was filtered and washed with i-Pr2O to provide (3Z)-1-acetyl-3-[ethoxy(phenyl)methylene]-2-oxoindoline-5-carboxylic acid (3.5 g, 33 %) 1H-NMR in DMSO-d6 12.3(bs,1H);8.61(d,1H); 8.22(d,1H); 7.90(dd,1H); 7.54(m,5H); 3.99(q,2H); 2.45(s,3H); 1.35(t,3H). tR: 3.82 min, MS(ESI):m/z(M+H)+352, (M+H)- 350.

The synthetic route of 102359-00-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Max-Planck-Gesellschaft zur Foerderung der Wissenschaften e.V.; Vichem Chemie Ltd.; Keri, Gyoergy; Oerfi, Laszlo; Horvath, Zoltan; Szokol, Balint; Dobos, Judit; Nemes, Zoltan; Szantay Kis, Csaba; Eroes, Danilel; Breza, Nora; Baska, Ferenc; Karlas, Alexander; Goedert, Sigrid; Meyer, Thomas F.; (133 pag.)EP3056202; (2016); A1;,
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Related Products 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.

5-Iodo-2-oxindole 2-Oxindole (82.9 g) was suspended in 630 mL of acetic acid with mechanical stirring and the mixture cooled to 10 C. in an ice water bath. Solid N-iodosuccinimide (175 g) was added in portions over 10 minutes. After the addition was complete the mixture was stirred for 1.0 hour at 10 C. The suspended solid which had always present became very thick at this time. The solid was collected by vacuum filtration, washed with 100 mL of 50% acetic acid in water and then with 200 mL of water and sucked dry for 20 minutes in the funnel. The product was dried under vacuum to give 93.5 g (36%) of 5-iodo-2-oxindole containing about 5% 2-oxindole by proton NMR.

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; Sugen, Inc.; US6486185; (2002); B1;; ; Patent; Sugen, Inc.; US6114371; (2000); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem