Category: indolines-derivatives

Related Products of 87-48-9, 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. 87-48-9 name is 5-Bromoindoline-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.

5-bromo-indole-2,3-dione (2.25g, 10mmol), ethylene glycol (45 mL) and heatIt was added KOH (1.68g, 30mmol) in a mixture of hydrazine hydrate (1.06g, 21.10mmol). The reaction mixture was stirred for 4 hours at 80 C.. The mixture was cooled to room temperature, poured into ice-cold water, with 12N hydrochloric acid was adjusted to pH 1 ~ 2, and stirred at room temperature for 12 hours. The mixture was filtered solid was washed with water (5 mL), and dried to give the crude product which was purified juice dim over a column chromatography (methanol in dichloromethane, 0.5% v / v), 0601 -194 as a yellow solid (785mg, 37%).

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

Reference:
Patent; CURIS INCORPORATED; CAI, XIONG; ZHAI, HAIXIAO; LAI, CHENG-JUNG; QIAN, CHANGGENG; (290 pag.)JP2015/187145; (2015); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

1914-02-9, name is 3,3-Dimethylindoline, 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. SDS of cas: 1914-02-9

Example 18b Synthesis of 2-[2-(3,3-dimethyl-2,3-dihydroindol-1-yl)-2-oxoethyl]-6-morpholin(D4)-4-yl-3H-pyrimidin-4-one Step 1b: Synthesis of 2-(4-chloro-6-methoxypyrimidin-2-yl)-1-(3,3-dimethyl-2,3-dihydroindol-1-yl)ethanone 0.5 g of the sodium salt of (4-methoxy-6-chloropyrimidin-2-yl)acetic acid (example 8b, step 3b), 0.33 g of 3,3-dimethyl-2,3-dihydro-1H-indole (CAS 1914-02-9), 0.4 ml of pyridine and 5 ml of dimethylformamide are placed in a three-necked flask so as to obtain a homogeneous brown solution. 512 mg of N-[3-(dimethylamino)propyl]-N?-ethylcarbodiimide are added at ambient temperature and the mixture is stirred at ambient temperature for 20 hours. The resulting product is concentrated in a rotary evaporator under vacuum, 40 ml of water are added, extraction is carried out with 3 times approximately 25 ml of dichloromethane, washing is carried out with 50 ml of saturated NaCl solution, drying is carried out over MgSO4, and the resulting product is filtered through a VF filter. The compound obtained is purified by chromatography on silica gel (40-63 mum), elution being carried out with a 98/2 dichloromethane/methanol mixture. The fractions containing the expected compound are combined and evaporated under reduced pressure. 2-(4-Chloro-6-methoxypyrimidin-2-yl)-1-(3,3-dimethyl-2,3-dihydroindol-1-yl)ethanone is isolated: 0.3 g of a yellow oil; yield 41%, which is used as it is in the next step.

The synthetic route of 1914-02-9 has been constantly updated, and we look forward to future research findings.

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;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

20870-79-5, name is 5-Nitroindolin-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 5-Nitroindolin-2-one

General procedure: To a suspension of 5-nitro-3-substituted-2-oxindole derivatives 8-12 or commercially available 5-nitroindolin-2-one (1 mmol) in amixture of ethanol and water (10 mL, 4:1 v/v) was added iron powder (560 mg.10 mmol,10 equiv.) and NH4Cl (134 mg, 2.5 mmol,2.5 equiv.). The mixture was refluxed for 2 h, cooled and filteredthrough Celite. The filtrate was diluted with water (5 mL) andextracted with dichloromethane (3 x 10 mL). The combinedorganic layers were washed with water (10 mL) and brine (10 mL),dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude residue was purified by crystallization withethyl ether.

The synthetic route of 20870-79-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Romagnoli, Romeo; Baraldi, Pier Giovanni; Prencipe, Filippo; Oliva, Paola; Baraldi, Stefania; Salvador, Maria Kimatrai; Lopez-Cara, Luisa Carlota; Bortolozzi, Roberta; Mattiuzzo, Elena; Basso, Giuseppe; Viola, Giampietro; European Journal of Medicinal Chemistry; vol. 134; (2017); p. 258 – 270;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 222036-66-0, name is 5-Aminoisoindolin-1-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 222036-66-0, SDS of cas: 222036-66-0

A mixture of 3-(8-(5,6-dimethoxypyridin-2-ylamino)imidazo[l ,2-b]pyridazin-6-yl)benzoic acid (100 mg, 0.26 mmol), 5-aminoisoindolin-l-one (38 mg, 0.26 mmol), 1 -methyl- lH-imidzole (84 mg, 1.02 mmol) and EDCI (196 mg, 1.02 mmol) in DMF (3 mL) was stirred for 16 h at room temperature. Ethyl acetate (5 mL) and water (5 mL) were added. The organic layer was separated and the aqueous phase was extracted with ethyl acetate (20 mL). The organic phases were combined and washed with brine (10 mL) then dried over Na2S04. The residue was concentrated and triturated with MeOH (2 mL) to give 3-(8-(5,6-dimethoxypyridin-2-ylamino) imidazo[l ,2- b]pyridazin-6-yl)-N-(l-oxoisoindolin-5-yl)benzamide (26 mg, 20 percent) as a yellow solid. 1H NMR (300 MHz, DMSO): delta 10.68 (s, 1H), 9.97 (s, 1H), 8.61 (s, 1H), 8.52 (s, 1H), 8.44 (s, 1H), 8.24 – 8.08 (m, 4 h), 7.82 – 7.64 (m, 4 h), 7.41 (d, 1H, J = 8.7 Hz), 7.1 1 (d, 1H, J = 8.4 Hz), 4.39 (s, 2H), 4.02 (s, 3H), 3.76 (s, 3H). LC-MS : [M+H]+, 521.9, tR = 1.434 min, HPLC: 96.12 percent at 214nm, 96.79 percent at 254nm, tR = 3.673 min.

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; F. HOFFMANN-LA ROCHE AG; HERMANN, Johannes Cornelius; KUGLSTATTER, Andreas; LUCAS, Matthew C.; PADILLA, Fernando; WANNER, Jutta; ZHANG, Xiaohu; WO2013/64445; (2013); A1;,
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. 446292-08-6, name is (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., COA of Formula: C22H19N3O6

Example 4: Preparation of 4-{4-[5(S)-(amino methyl)-2-oxo-l,3-oxazolidin-3- yI]phenyl}morpholin-3-one (II)Methanol (240 ml) and Hydrazine hydrate (26 g) were added to a flask containing the (2-{2-Oxo-3-[4-(3-oxo-morpholin-4-yl)-phenyl]-oxazolidin-5-ylmethyl}-isoindole-l ,3-dione (40 g), heated for 1 hour at reflux temperature and cooled to room temperature. After completion of the reaction, 500ml of water was added to the reaction mass and was extracted with methylene dichloride (300 ml). The combined extractions were washed with water (100 ml) and the solvent was distilled completely to give 20 gms of the title compound.

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; SYMED LABS LIMITED; MOHAN RAO, dodda; KRISHNA REDDY, pingili; ANNA REDDY, ambati; VENKAT REDDY, buthukuri; WO2012/32533; (2012); 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. 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-one, A new synthetic method of this compound is introduced below., SDS of cas: 118289-55-7

Examples 1. Preparation of ZPR in n-BuOH with 0.9 mol NaI. In a three necked flask was charged n-BuOH (50 ml) and 1, 2-Benzisothiazole-3- piperazinyl hydrochloride (BITP HC1) (5.6g, 0.022 mol), and the obtained slurry was heated at 100C. To the slurry, Na2CO3 (11.6 g), NaI (3g) and 5- (2-chloroethyl)-6- chloro-1, 3-dihydro-indole-2 (2H)-one (CEI) (7. 5g, 0.032 mol) were added at 110C. The heating was maintained for 8. 5h. After cooling the reaction product was filtrated, washed with hexane and water, and dried at 60 C. The dried product weights 8.12g and has an HPLC purity 92.7%.

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; TEVA PHARMACEUTICAL INDUSTRIES LTD.; TEVA PHARMACEUTICALS USA, INC.; WO2005/40160; (2005); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 104618-32-8, A common heterocyclic compound, 104618-32-8, name is 2-(4-Oxocyclohexyl)isoindoline-1,3-dione, molecular formula is C14H13NO3, 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 solution of commercially available 4-bromophenyl hydrazine (1.46 g, 6.5 mmol) in ethanol (50 mL) was added preparative example 28 step C (1.6 g, 6.5 mmol) in ethanol (15 mL). The reaction mixture was stirred for 2 h at room temperature. The solvent was removed to give the title compound as a solid (2.9 g, quantitative).1H-NMR (400 MHz, DMSO-d6): delta=7.85-7.86 (m, 4H), 7.31 (d, 8.4 Hz, 2H), 7.00 (d, 2H), 4.32-4.38 (m, 1H), 3.12-3.15 (m, 1H), 2.36-2.51 (m, 2.19-2.28 (m, 2H), 1.92-2.06 (m, 3H).

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; AC Immune, S.A.; US2011/280808; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

6941-75-9, name is 5-Bromoisoindoline-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. Computed Properties of C8H4BrNO2

5-bromoisoindoline-1,3-dione (2.73 g, 12.1 mmol)Was suspended in tetrahydrofuran (20 mL)To this was added borane-tetrahydrofuran (1 M, 48 mL).The reaction was refluxed overnight and cooled to 0 C,Followed by methanol (30 mL),2M hydrochloric acid (30 mL).The mixture was refluxed for 2 hours,Cooled to room temperature and concentrated under reduced pressure.The residue was partitioned between dichloromethane(50 mL) and water (50 mL). The separated aqueous phase was washed with dichloromethane (50 mL x 2) and adjusted to pH with 1 M sodium hydroxide solutionTo 11 and extraction with dichloromethane (80 mL x 4). The combined organic phases were dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure,The crude product was obtained as a dark brown oil (1.3 g, 54%),The product was purified and used directly in the next step.

The synthetic route of 6941-75-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jiatuo Sciences Corporation; Xi Ning; Wang Ruyong; Wang Liang; (112 pag.)CN104016979; (2017); B;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 1029691-06-2, 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. 1029691-06-2, name is 2-(3-Oxocyclopentyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

PREPARATION 2(R,S)-2-(7-Bromo-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl)-isoindole-1,3-dione In a 5 L flask is mixed (R,S)-2-(3-oxo-cyclopentyl)-isoindole-1,3-dione (295.3 g, 1.29 mol), 4-bromophenyl hydrazine-HCl (287.9 g, 1.29 mol) and glacial acetic acid (3 L) with mechanical stirring. The reaction is refluxed for 5 h, and then cooled to room temperature. The reaction is poured into water (4 L) with rapid stirring. The solid is collected by vacuum filtration, washed with water (4 L), and air-dried for 30 min. The solid is slurried with MeOH (700 mL), collected by vacuum filtration and rinsed with MeOH (100 mL). The gray solid is air dried for 2 h, then dried overnight in a 50 C. vacuum oven to obtain 414.67 g (84%) of the title compound as a dark solid. ES/MS m/z (79Br/81Br) 381/383 [M+H]+.

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

Reference:
Patent; ELI LILLY AND COMPANY; US2011/118326; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 1127-59-9, A common heterocyclic compound, 1127-59-9, name is 7-Methylindoline-2,3-dione, molecular formula is C9H7NO2, 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 solution of potassium hydroxide (11.8 g, 211 mmol, 5 eq) in water (80 mL) was added 7-methylindoline-2,3-dione (6.8 g, 42.2 mmol, 1 eq) in ethanol (100 mL). The mixture was stirred at 76° C. then acetone (50 mL) was added. The mixture was heated to 76° C. for 3 days. Acetone and ethanol were removed under reduced pressure. Impurities were removed by extraction with dichloromethane. Aqueous layer was lyophilized to give 2,8-dimethylquinoline-4-carboxylic acid as a brown solid (7.05 g, 83percent).

The synthetic route of 1127-59-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GALDERMA RESEARCH & DEVELOPMENT; OUVRY, Gilles; HARRIS, Craig Steven; BHURRUTH-ALCOR, Yushma; (65 pag.)US2017/247353; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem