Category: indolines-derivatives

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. 25369-33-9, name is 7-Chloroindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 7-Chloroindolin-2-one

Example 54Preparation of 7-chloro-5-[Y2-((‘l S,2S)-2-[l-(5-chloropyrimidin-2-yl)piperidin-4- yli cvclopropyU ethvDaminol -1.3 -dihvdro-2H-indol-2-oneStep 1 ; 7-chloro-5-nitro-13-dihvdro-2H-indol-2-one7-chloro-1,3-dihydro-2H-indol-2-one (8.Og, 47.7 mmol) was slurried in H2SO4 (cone, 86 ml) and the mixture cooled to -45 C. A solution of fuming nitric acid (>90%, 3.34 g, 52.9 mmol) in H2SO4 (20 ml) was added drop wise, while maintaining the temperature at -45 C throughout the addition. The mixture was allowed to slowly warm to RT and stirred overnight. The mixture was poured into stirred ice-cold water (1500 ml). A white precipitate resulted, and the slurry was aged at 0 C for 1 hour. The solid was collected by filtration, triturated with cold water (2x)? and dissolved into EtOAc (1 L). This mixture was filtered, washed with basic brine (containing sodium bicarbonate), dried over Na2SO4, filtered, and the volatiles removed in vacuum to give the titled compound.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 25369-33-9.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WOOD, Harold, B.; ADAMS, Alan, D.; SZEWCZYK, Jason, W.; ZHANG, Yong; YANG, Meng; WO2011/19538; (2011); A1;,
Indoline – Wikipedia,
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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, COA of Formula: C8H3Cl2NO2

(1) 1-Methyl-4,6-dichloroisatin A mixture of 60% NaH (20.5 mg), 4,6-dichloroisatin (947 mg), and iodomethane (0.328 mL) in THF (20 mL) were stirred overnight at room temperature, poured into 1 N hydrochloric acid, and extracted with ethyl acetate. The extracts were washed with sat. aqueous NaCl, dried over MgSO4, and concentrated. The residue was washed with hexane to give the title compound (849 mg, 84%). 1H-NMR (DMSO-d6, 300 MHz) delta 3.12-3.11 (3H, m), 7.33-7.30 (2H, m).

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; Sumitomo Pharmaceuticals Co., Ltd.; US6576656; (2003); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 3339-73-9, name is 3-(1,3-Dioxoisoindolin-2-yl)propanoic acid, molecular formula is C11H9NO4, 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. Computed Properties of C11H9NO4

General procedure: The DCC (1.2 equiv) was added to the solution of 1 (0.2 mmol), DMAP (0.2 equiv), and appropriate carboxylic acid (1.2 equiv) in anhydrous CH2Cl2 (8 mL) at 0 C. The resulting mixture was stirred at room temperature until the starting material was not observed by TLC. The reaction mixture was filtered, and the residue was washed with CH2Cl2 (2 × 10 mL). Then, the CH2Cl2 solution was washed with 5% HCl (3 × 30 mL), saturated NaHCO3 (3 × 30 mL) and saturated NaCl (3 × 30 mL), respectively. Subsequently, the organic layer was dried over anhydrous Na2SO4 and concentrated to dryness under reduced pressure. At last, the residue was purified by column chromatography over the silica gel to yield the pure target compounds.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3339-73-9, its application will become more common.

Reference:
Article; Wang, Li-Jun; Geng, Chang-An; Ma, Yun-Bao; Huang, Xiao-Yan; Luo, Jie; Chen, Hao; Guo, Rui-Hua; Zhang, Xue-Mei; Chen, Ji-Jun; Bioorganic and Medicinal Chemistry; vol. 20; 9; (2012); p. 2877 – 2888;,
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Indoline | C8H9N – PubChem

These common heterocyclic compound, 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, 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: C9H7NO3

General procedure: Intermediates (7) (140 mg, 1.2 equiv.), PyBOP (1.2 equiv.) and DIPEA (1.5 equiv.) were added toDMF and stirred at room temperature for 20 min. Then, intermediates (4a-d) (1.0 equiv.) was addedand stirred at room temperature for 4 h. After completion of the reaction, the reaction mixture wasquenched with saturated NaCl solution (25 mL). The aqueous phase was extracted with DCM (25 ×3 mL). The DCM layer was combined and washed with brine solution (25 × 3 mL). The organic layerwas dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. Afterconcentration, the crude product was purified by silica gel column chromatograph using a methanolin DCM gradient (DCM: methanol= 60:1-5:1) yielded compounds 8i-l.

The synthetic route of 2-Oxoindoline-5-carboxylic Acid has been constantly updated, and we look forward to future research findings.

Reference:
Article; Guo, Yan; Yang, Hongyu; Huang, Zhongwei; Tian, Sen; Li, Qihang; Du, Chenxi; Chen, Tingkai; Liu, Yang; Sun, Haopeng; Liu, Zongliang; Molecules; vol. 25; 3; (2020);,
Indoline – Wikipedia,
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5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, belongs to indolines-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Product Details of 5332-26-3

By preheating the internal reactor is sufficiently dried, after substituting dry nitrogen, into the reactor, 4-[ (2-methacryloyloxy) halogenoethoxy]-4-aminobutyric oxopiperidine 11. 51g (0. 05mol), triethylamineborane 6. 07g (0. 06mol), dimethyl formamide (DMF) 150 ml is added. By heating the oil bath 65 C, while stirring, N-(bromomethylbiphenyl) tetrafluorophthalimide 12. 00g (0. 05mol) dissolved in 15 minutes to DMF100mL is added. After the first period, by distilling evaporator DMF, residue extracted with ethyl acetate is obtained. The extract is washed with water to 3 times, then the saturated aqueous solution of sodium bicarbonate, saturated saline successively washed, dried with sodium sulfate (desiccant). Furthermore, after the drying agent is then filtered by a Buchner funnel, distilling organic solvent. In this way, the eq. (M-20) shown (1, 3-dioxo isoindolin-2-yl) methyl 2-(methacryloyloxy) ethyl succinate (13. 95g (yield 72%))is obtained.

The synthetic route of 5332-26-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JSR CORPORATION; ASANO, YUSUKE; SATO, MITSUO; (60 pag.)JP2015/38072; (2015); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 101207-45-8, name is 2-(4-Methylbenzyl)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 101207-45-8, SDS of cas: 101207-45-8

General procedure: To the mixture of B(C6F5)3 (5.0mol%) and cyclic imides (1.0mmol) in dioxane, was added PhSiH3 (3.0mmol) slowly under an atmosphere of nitrogen. The reaction mixture was stirred and refluxed at 110C under an atmosphere of nitrogen. After the imide was consumed completely (detected by TLC) the mixture was added with aqueous ammonia (15mL) and extracted with CH2Cl2 (10mL×3). The combined organic phase was dried over Na2SO4, after removing the solvent under vacuum, the residue was purified by column chromatography to give the product.

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; Ding, Guangni; Wu, Xiaoyu; Lu, Bin; Lu, Wenkui; Zhang, Zhaoguo; Xie, Xiaomin; Tetrahedron; vol. 74; 11; (2018); p. 1144 – 1150;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 3676-85-5, These common heterocyclic compound, 3676-85-5, name is 5-Aminoisoindoline-1,3-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.

To a stirred solution of 5-amino-1H-isoindole-1,3(2H)-dione (1.0 g, 6.2 mmol) dissolved in sulfuric acid solution (2 mL of Con. H2SO4 in 7.5 mL of H2O) at 0 C., was added ice cold sodium nitrite solution (0.8 g in 2 mL of H2O) dropwise. After 45 min of stirring at 0 C., CuBr (3.4 g, 23.7 mmol) and HBr[48%] (13.6 mL, 4 vol. w.r.t. CuBr) were added at the same temperature. The resulting mixture was stirred at 80 C. for 8 h then poured into crushed ice. Filtered the solid, washed with ice cold water and dried thoroughly to give 0.6 g (43.0%) of 5-bromo-1H-isoindole-1,3(2H)-dione as a brown colour solid.

The synthetic route of 3676-85-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Deng, Jianghe; Kerns, Jeffrey K.; Jin, Qi; Lin, Guoliang; Lin, Xichen; Lindenmuth, Michael; Neipp, Christopher; Nie, Hong; Thomas, Sonia M.; Widdowson, Katherine L.; US2009/143372; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 132898-96-5, 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. 132898-96-5 name is 2,3-Dioxoindoline-5-sulfonyl chloride, 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.

Step 1: 5-{[(2R)-2-(Methoxymethyl)pyrrolidin-1-yl]sulfonyl}-1H-indole-2,3-dione To a stirred cold suspension of 2,3-dioxo-2,3-dihydro-1H-indol-5-sulfonyl chloride (5.00 g, 20.4 mmol) in a 1:1 mixture of THF: CHCl3 (140 mL) was added dropwise, via syringe pump, a solution of N,N-diisopropylethylamine (7.11 mL, 40.8 mmol, 2 eq) and (R)-2-(Methoxymethyl)pyrrolidine (3.27 mL, 26.5 mmol, 1.3 eq) in CHCl3 (60 mL) over a period of 1.5 hours with cooling in an ice bath. After stirring an additional 1 h, the reaction was concentrated. The crude product was purified on Biotage KP silica gel eluding with 95/5 CH2Cl2/CH3OH followed by a second chromatography on silica gel eluding with EtOAc to give 4.21 g (63.8%) of the title compound. NMR (400 MHz, DMSO-d6): consistent.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,3-Dioxoindoline-5-sulfonyl chloride, and friends who are interested can also refer to it.

Reference:
Patent; Wyeth; US2005/250798; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 3339-73-9, name is 3-(1,3-Dioxoisoindolin-2-yl)propanoic acid, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 3-(1,3-Dioxoisoindolin-2-yl)propanoic acid

Into a 1000-mL 4-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 3-(l,3-dioxo-2,3-dihydro-lH-isoindol-2- yl)propanoic acid (40 g, 182.49 mmol, 1.00 equiv) in water (250 mL). This was followed by the addition of aniline (17 g, 182.55 mmol, 1.00 equiv). To this was added sodium carbonate (9.6 g, 90.57 mmol, 0.50 equiv). The resulting solution was stirred for 3 h at 25 C. The pH value of the solution was adjusted to 5-6 with hydrochloric acid (1 mol/L). The solids were collected by filtration. The filter cake was washed with 1×200 mL of water. This resulted in 40 g (74%) of 3-(l,3-dioxo- 2,3-dihydro-lH-isoindol-2-yl)-N-phenylpropanamide as a white solid. MS (ESI) m/z 295 ([M + H]+)

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 3339-73-9.

Reference:
Patent; REXAHN PHARMACEUTICALS, INC.; LEE, Young Bok; KIM, Jae Min; KIM, Deog Joong; AHN, Chang-Ho; WO2014/143960; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 129487-92-9, name is tert-Butyl 5-aminoindoline-1-carboxylate, 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 129487-92-9, Recommanded Product: 129487-92-9

A mixture of 2-chloro-6-methylnicotinic acid (3.43 g), tert-butyl 5-AMINO-1-INDOLINECARBOXYLATE (5.15 g), 1- hydroxybenzotriazole hydrate (3.21 g) and 1- [3- (dimethylamino) PROPYL]-3-ETHYLCARBODIIMIDE (3.26 g) in N, N- dimethylformamide (30 ml) was stirred at ambient temperature overnight. The reaction mixture was poured into a mixture of ethyl acetate and water, and the organic layer was washed with brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was chromatographed on silica gel eluting with ethyl acetate and n-hexane (6: 4 v/v). The eluted fractions containing the desired product were collected and evaporated in vacuo to give tert-butyl 5-{[(2- chloro-6-methyl-3-pyridinyl) carbonyl] AMINO}-1- indolinecarboxylate (6.65 g). 1H-NMR (DMSO-d6) : 8 1.51 (9H, s), 2.51 (3H, s), 3.07 (2H, T, J=8.5 Hz), 3.91 (2H, t, J=8.5 Hz), 7.37-7. 41 (2H, m), 7.52-7. 69 (2H, m), 7.92 (1H, d, J=7.6 Hz), 10.43 (1H, s)

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; FUJISAWA PHARMACEUTICAL CO., LTD.; DAISO CO., LTD.; WO2004/39795; (2004); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem