Category: indolines-derivatives

These common heterocyclic compound, 3891-07-4, name is 2-(2-Hydroxyethyl)isoindoline-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. SDS of cas: 3891-07-4

To a solution of 4a (1.88 g, 20 mmol), N-(2-hydroxyethyl)phthalimide (3.82 g, 20 mmol) and triphenylphosphine (7.87 g, 30 mmol) in tetrahydrofuran (30 mL) was added dropwise a solution of diethyl azodicarboxylate (4.7 mL, 30 mmol) in tetrahydrofuran (10 mL) at 0C over 0.5 h. The mixture was stirred at the same temperature for 6h and concentrated under reduced pressure. The residue was diluted in diethyl ether and stirred at -5 to 0C for 30 min and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel), eluting with petroleum ether and ethyl acetate (6:1, v/v) to give 5a (5.02g, 94 %) as a off-white solid.

The synthetic route of 2-(2-Hydroxyethyl)isoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Minghua; Ye, Cheng; Liu, Mingliang; Wu, Zhaoyang; Li, Linhu; Wang, Chunlan; Liu, Xiujun; Guo, Huiyuan; Bioorganic and Medicinal Chemistry Letters; vol. 25; 14; (2015); p. 2782 – 2787;,
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Application of 897957-06-1,Some common heterocyclic compound, 897957-06-1, name is 6-Bromo-1-methylindolin-2-one, molecular formula is C9H8BrNO, 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.

Step 3: Synthesis of Intermediate R12To 1-5.2 (32.0 g, 142 mmol) in anhydrous dioxane (400 mL) is added Ri 1 (54.4 g, 241 mmol) andpotassium acetate (41.6 g, 424 mmol). The mixture is purged with Argon, [1, 1?-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) as a complex with dichloromethane (11.2 g, 14 mmol) is added and the mixture is heated to 90 C for 2 h. The reaction mixture is diluted with ethyl acetate and water, the organic layer is washed with water, dried over Mg504 and concentrated. The residue is purified via flash chromatography (cyclohexane / EA = 70:30). Yield72%, m/z 274 [M+H]+, rt 0.67 mi LC-MS Method VOil SOl.

The synthetic route of 897957-06-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ANDERSKEWITZ, Ralf; GRAUERT, Matthias; GRUNDL, Marc; OOST, Thorsten; PAUTSCH, Alexander; PETERS, Stefan; WO2014/140091; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

603-62-3, name is 3-Nitrophthalimide, 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. name: 3-Nitrophthalimide

General procedure: 1 [43] (500 mmol) and 2 (500 mmol) were dissolved in acetonitrile(50 mL), then Cs2CO3 (204 mg, 625 mmol) was added in abovesolution. The resulting mixture was stirring overnight at roomtemperature under an inert atmosphere. After the reactioncompleted, the solvent was removed under vacuum and the residue was purified by silica gel column chromatography (petroleumether/ethyl acetate, 3/1, v/v).HP1, red solid, 93 mg, 36% yield;

The synthetic route of 603-62-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Li, Biao; He, Zhaoshuai; Zhou, Hanxin; Zhang, Han; Li, Wu; Cheng, Tanyu; Liu, Guohua; Dyes and Pigments; vol. 146; (2017); p. 300 – 304;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 2436-29-5, name is 3-(1,3-Dioxoisoindolin-2-yl)propanal, 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 2436-29-5, Safety of 3-(1,3-Dioxoisoindolin-2-yl)propanal

Example 12d (0.06 g, 0.135 mmol) and 3-(l ,3-dioxoEomdoliiv2-yl)propa-ial (0082 g, 0.406 mmol) were combined in tetrahydiiofuran (1 .353 mL) under nitto gen and treated drop-wise with 1 M utanium(IV) chloride in toluene (0.406 mL, 0.406 mmol) . The reaction mixture was stirred lor 18 hours at 60 * C, cooled to artfc ient temperature, and partitioned b etwee II ethyl acetate and water. The organic layer was was lied with s aturated aqueous sodium cluotide, dried over arfoydrous sodium sulfate, filtered and concentrated. Irification b y revers e phase HPLC (C IS, C CNAvater (0.1 “A TFA), 0- 100 % gradient) provided the title compound. (0.018 g, 21 ). NMR (500 MHz, DMS O-^ 6 11 94 (d, J = 2.14 Hz, 1H1 7.88 (d, J = 1 53 Hz, 1H), 7.80 – 786 (m, 4H), 7.72 (s, 1H), 7.31 (d, J = 2.75 Hz, IK), 728 (dd, J = 3D9, 1.98 Hz, 1 H), 7.02 – 7.10 (m, 2H), 6.77 – 6.83 (m, 1H), 6.65 – 6.72 (m, 1 5.06 – 5.1 1 (m. 1H), 4.40 – 4.57 (m, 2H), 3.70 – 3.79 (m, 1H), 3 65 ( , 3H), 354 – 3.63 (m, lH), 2.95 (s, 3H), 1 91 – 2.07 (m, 1 1.62 (dd, J = 13.12, 5.19 Hz, 1H). MS (ES I+) mfe 629 (M+H) 1.

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, 3-(1,3-Dioxoisoindolin-2-yl)propanal, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ABBVIE INC.; ABBVIE PHARMACEUTICAL TRADING (SHANGHAI) CO., LTD.; FIDANZE, Steven D.; LIU, Dachun; MANTEI, Robert A.; MCDANIEL, Keith F.; PRATT, John; SHEPPARD, George S.; WANG, Le; BOGDAN, Andrew; HOLMS, James H.; DIETRICH, Justin D.; MARJANOVIC, Jasmina; HASVOLD, Lisa A.; DAI, Yujia; WO2014/139324; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 59-48-3, name is 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. Product Details of 59-48-3

To a solution of oxindole (26 g) in 100 mL of concentrated sulfuric acid at -15 C. was added fuming nitric acid (8.4 mL) dropwise. Careful attention was paid to maintain the reaction temperature at -15 C. After the addition was complete, the reaction was stirred for 30 minutes and then poured into ice water. A yellow precipitate was formed which was isolated by filtration to provide 34 grams (98%) of 5-nitro oxindole.

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

Reference:
Patent; Pfizer Inc; US2005/256144; (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. 3485-84-5, name is N-Vinylphthalimide, This compound has unique chemical properties. The synthetic route is as follows., Formula: C10H7NO2

The product of preparation 97 (5.0 g, 15 mmol), N-vinylphthalimide (2.62 g, 15.1 mmol), tri-ortho-tolylphosphine (473 mg, 1.55 mmol), palladium (II) acetate (98 mg, 0.4 mmol) and N, N-diisopropylethylamine (30 mL, 172 mmol) in acetonitrile (35 mL) was heated under reflux for 16 hours. The reaction mixture was then cooled to room temperature and the precipitate was filtered off. The solid was then dissolved in dichloromethane, activated charcoal was added, and the solution was filtered through CeliteNo.. The filtrate was concentrated in vacuo and the residue was re-crystallised from hot dichloromethane/methanol to afford the title compound as a yellow solid in 55% yield, 3.5 g. H NMR (400MHz, CDCI3) 6 : 2.20 (6H, s), 3.80 (2H, s), 4.30 (2H, d), 6.0 (1H, brs), 6.90 (2H, m), 7.01 (1H, m), 7.18 (1H, m), 7.26-7. 40 (4H, m), 7. 56-7. 61 (1 H, m), 7.75 (2H, m), 7.88 (2H, m)

According to the analysis of related databases, 3485-84-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER LIMITED; PFIZER INC.; WO2005/92840; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 15861-23-1, name is Indoline-5-carbonitrile, 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 15861-23-1, name: Indoline-5-carbonitrile

A mixture of the compound of Part D (0.3 g, 0.72 mol) and 5-cyanoindoline (0.1 g, 0.694 mmol) in 2.5 mL 1,2-dichloroethane was stirred under N2 for 10 min, followed by the addition of sodium triacetoxyborohydride (0.22 g, 1.04 mmol, 1.5 eq.). The mixture was then stirred overnight at rt. The reaction was quenched by addition of water and 1M NaOH and extracted 3¡Á with CH2Cl2. Extracts were combined, washed with brine and dried over anh. Na2SO4, filtered and evaporated. Chromatography on silica gel (hexane/ethyl acetate 75:25) provided the desired alkylated product as a white foam (120 mg, 32%). 1HNMR (300 MHz, CDCl3) delta 8.27 (s, 1H); 7.93 (d, 1H); 7.30 (6H, m); 7.13-7.02 (6H, m); 6.18 (1H, bt), 5.88 (d, 1H, J=6 Hz); 5.03 (2H, dd, J=18, 10.8); 3.96, (s, 2H); 3.32 (t, 2H, J=6 Hz); 2.81 (t, 2H, J=6 Hz); 1.92 (m, 1H); 1.00 (6H, d, J=6.6 Hz). MS m/z 544.3 (M+H)+.

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; Smallheer, Joanne M.; Quan, Mimi L.; Wang, Shuaige; Bisacchi, Gregory S.; US2004/220206; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 3335-98-6, 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. 3335-98-6 name is 1-Phenyloxindole, 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: An oven-dried reflux tube equipped with a magnetic stir bar and a Teflon stopcock was charged with aryl halide (1 mmol), oxindole (1 mmol),potassium carbonate (1.1 mmol), catalyst nanoparticles (0.05 mmol)and 1,4-dioxane (2 ml) and heated at 70 C. The mixture was vigorously stirred under these reaction conditions and completion of the reaction was monitored by TLC (EtOAc: n-hexane, 25:75). After completion of the reaction, the reaction mixture was cooled to room temperature, the magnetic nanoparticles of the catalyst were collected using a magnet. Ethyl acetate (5 mL) and water (10 mL)were added to the mixture in the next step. The aqueous layer was furtherextracted by ethyl acetate (2*5 mL). The combined organic layerswere washed with saturated brine, dried over CaCl2, filtered, and concentrated to give a residue which was purified by recrystallization from ethanol and water or by column chromatography on silica gelusing EtOAc: n-hexane, 1:7.

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

Reference:
Article; Moghaddam, Firouz Matloubi; Tavakoli, Ghazal; Latifi, Fatemeh; Saeednia, Borna; Catalysis Communications; vol. 75; (2016); p. 37 – 41;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

13220-46-7, name is 4-Methylindolin-2-one, 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. Safety of 4-Methylindolin-2-one

(S)-5-(2-Hydroxy-3-morpholin-4-yl-propyl)-3-methyl-4-oxo-1,4,5,6,7,8-hexahydro-pyrrolo[3,2-c]azepine-2-carbaldehyde 78f (40 mg, 0.12 mmol 1) and 4-methyl-1,3-dihydro-indol-2-one (18 mg, 0.12 mmol) were dissolved in 1.5 ml of ethanol, and added with 6mul of piperidine to the solution at room temperature. Upon completion of the addition, the reaction mixture was stirred at 45C for 16 hours. After thin lay chromatography showed the disappearance of starting materials, the reaction mixture was naturally cooled down to room temperature, and filtered. The filter cake was washed with anhydrous ethanol (1 ml¡Á2) and dried to obtain the title compound (S,Z)-5-(2-hydroxy-3-morpholinopropyl)-3-methyl-2-((4-methyl-2-oxoindolin-3-ylide ne)methyl)-5,6,7,8-tetrahydropyrrolo[3,2-c]azepin-4(1H)-one 83 (35 mg, yield 63.6%) as a yellow solid. MSm/z(ESI): 465.2(M+1) 1NMR(400 MHz, DMSO-d6) delta13.715(s, 1H, pyrrole-NH),10.934(s, 1H, indole-NH),7.572(s, 1H, -CH=C), 7.057 (t, 1H, -ArH), 6.840?6.821(d, 1H, -ArH), 6.790?6.771(d, 1H, -ArH), 4.737?4.725(d, 1H, -OH), 3.92(m, 1H, -CHOH), 3.75 (dd, 1H, seven-membered ring intra amide -NCH2), 3.58(t, 4H, morpholin2¡Á-CH2O), 3.441 (m, 2H, seven-membered ring -NCH2), 3.15(m, 1H, seven-membered ring outer amide-NCH2), 2.939(t, 2H, -CH2CH=C), 2.594(s, 3H, pyrrole-CH3), 2.426 (m, 4H, morpholin intra 2¡Á-CH2N), 2.388(s, 3H, pyrrole-CH3), 2.309?2.293(m, 2H, morpholin outer-NCH2), 2.078(m, 2H, seven-membered ring CH2-CH2-CH2)

The synthetic route of 13220-46-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Hengrui Pharmaceutical Co. Ltd.; EP2157093; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 39603-24-2, 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. 39603-24-2 name is 5,7-Dimethylindoline-2,3-dione, 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: Isatin (1mmol), 1,3-indanedione (1mmol), ethyl acetoacetate (1mmol), and NH4OAc (1mmol) were placed in a 25-mL round-bottomed flask in ethanol:water (9:1) (5mL). The resulting mixture was stirred at room temperature for time mentioned in Table 2, until completion of the reaction as monitored by thin-layer chromatography (TLC). After completion of the reaction, the mixture was filtered and washed with a small quantity of ethanol to furnish pure spiro[4H-indeno-[1,2-b]pyridine-4,3′-[3H]indoles]. The structure of products was confirmed by IR, 1H and 13C NMR, GCMS, HRMS, and elemental analysis.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5,7-Dimethylindoline-2,3-dione, and friends who are interested can also refer to it.

Reference:
Article; Dige, Nilam C.; Pore, Dattaprasad M.; Synthetic Communications; vol. 45; 21; (2015); p. 2498 – 2510;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem