Indolines-derivatives

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,
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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,
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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

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

These common heterocyclic compound, 132898-96-5, name is 2,3-Dioxoindoline-5-sulfonyl chloride, 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. Application In Synthesis of 2,3-Dioxoindoline-5-sulfonyl chloride

General procedure: To a stirred solution of the N-Boc-protected pyrrolidine (1.0 mmol) in dry DCM (3 mL) at 0 C under argon atmosphere, TFA (1.14 g, 10.0 mmol) was added dropwise. The obtained solution was stirred at 0 C for 30 min followed by stirring at r.t. for 2 h. Subsequently, the solution was poured to cold 10% aq. NaOH (15 mL) and extracted with DCM (3 × 15 mL). The combined organic phases were dried over MgSO4 and concentrated under reduced pressure resulting in the corresponding unprotected pyrrolidine, which was used in the next step without further purification. The free pyrrolidine (ca. 1 mmol) from the previous step was then taken up in CHCl3 (2.2 mL) and DIPEA (2.0 mmol) was added. The solution was added dropwise to a stirred solution of 5-chlorosulfonyl isatin (1.5 mmol) in CHCl3/THF (1:1, 15 mL) at room temperature. The resulting mixture was stirred further for 1 h and the solvent was removed under reduced pressure. After purification by flash column chromatography the target isatin sulfonamide was obtained.

The synthetic route of 2,3-Dioxoindoline-5-sulfonyl chloride has been constantly updated, and we look forward to future research findings.

Reference:
Article; Limpachayaporn, Panupun; Riemann, Burkhard; Kopka, Klaus; Schober, Otmar; Schaefers, Michael; Haufe, Guenter; European Journal of Medicinal Chemistry; vol. 64; (2013); p. 562 – 578;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. category: indolines-derivatives

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.

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

Reference:
Article; Ma, Yong-Gang; Li, Chao; Yao, Chang-Sheng; Wang, Xiang-Shan; Tetrahedron; vol. 72; 27-28; (2016); p. 3844 – 3850;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 3484-35-3, 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. 3484-35-3 name is 5-Methylindolin-2-one, 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: The mixture of oxindole 1 (0.1 mmol), beta,gamma-unsaturated alpha-keto ester 2 (0.12 mmol),DABCO (0.02 mmol) in 1 mL H2O were stirred at room temperature. After stirringfor the indicated time, the mixture was extracted with ethyl acetate. The combinedorganic phase was dried over Na2SO4 and concentrated in vacuo. The residue wasfurther purified by washing with PE/EA to afford the desired products.

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

Reference:
Article; Han, Man-Yi; Pan, Ping; Sheng, Fei-Fei; Synlett; vol. 28; 11; (2017); p. 1378 – 1382;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 4403-36-5, 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. 4403-36-5, name is 2-(1,3-Dioxoisoindolin-2-yl)ethanesulfonylchloride, This compound has unique chemical properties. The synthetic route is as follows.

(2R,5S)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-ethanesulfonic acid 5-chloro-2-{2-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzylamide To a solution of (2R,5S)-5-chloro-2-{2-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzyl amine (0.060 g, 0.143 mmol) in methylene chloride (3 mL) was added 2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethanesulfonyl chloride (0.043 g, 0.150 mmol) and triethylamine (0.060 mL, 0.43 mmol) and the solution was stirred 1 hr at ambient temperature. The reaction was diluted with saturated aqueous sodium hydrogen carbonate and extracted with methylene chloride. The combined organics were dried over magnesium sulfate, filtered and concentrated in vacuo. Chromatography on silica gel gave the title compound (0.073 g, 77%).

The chemical industry reduces the impact on the environment during synthesis 2-(1,3-Dioxoisoindolin-2-yl)ethanesulfonylchloride. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Blumberg, Laura C.; Brown, Matthew F.; Gladue, Ronald P.; McGlynn, Molly A.; Poss, Christopher S.; US2002/107255; (2002); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 99365-40-9, 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. 99365-40-9, name is 6-Bromoindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of 5-bromo-1,3-dihydro-2H-indole-2-one (1.272 g, 6 mmol) in THF(15 ml) was added a solution of NaN(SiMe3)2 in THF (30 ml, 30 mmol). The reaction mixture was cooled to -78 C and stirring was continued at the same temperature for 0.5 h. The 2-chloro-N-(2-chloroethyl)-N-methyl ethylamine hydrochloride (1.155 g, 6 mmol) was added to the mixture, continued to stir at -78 C for 0.5 h, then stirred for 2 d at room temperature (TLC control). 4 M HCl (10 ml) was added, the mixture was adjusted pH to 10 with concentrated ammonia and extracted with CH2Cl2 (3 × 20 ml). The combined organic layer was dried (3 g of Na2SO4) and concentrated to afford the crude product, which was purified by FC with MeOH/CH2Cl2.

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

Reference:
Article; Ye, Lianbao; Tian, Yuanxin; Li, Zhonghuang; Jin, Hong; Zhu, Zhengguang; Wan, Shanhe; Zhang, Junyan; Yu, Pengjiu; Zhang, Jiajie; Wu, Shuguang; European Journal of Medicinal Chemistry; vol. 50; (2012); p. 370 – 375;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 7477-63-6, name is 7-Chloroisatin, 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 7477-63-6, SDS of cas: 7477-63-6

General procedure: To the respective solution of isatins 1a-g (1 mmol) inDMF(3mL) were added K2CO3 (165.5mg, 1.2 mmol). The resultingmixtures were stirred at 80 C for 1 h, then KI (8.3 mg,0.05 mmol) was added. After stirring for further 15 min,0.15mL of a solution of propargyl bromide 80% in toluenewas added dropwise slowly into the mixtures. The reactionmixtures were again stirred at 60 C for 3 h. Upon completionof the reaction, the resulting mixtures were cooled, pouredinto ice-cold water and acidified to pH?4. The orange solidsformed were filtered and dried to give the propargylatedisatins2, which were used for the next step without furtherpurification.

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, 7-Chloroisatin, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Dung, Do Thi Mai; Hai, Pham-The; Anh, Duong Tien; Huong, Le-Thi-Thu; Yen, Nguyen Thi Kim; Han, Byung Woo; Park, Eun Jae; Choi, Yeo Jin; Kang, Jong Soon; Hue, Van-Thi-My; Han, Sang-Bae; Nam, Nguyen-Hai; Journal of Chemical Sciences; vol. 130; 6; (2018);,
Indoline – Wikipedia,
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