Category: indolines-derivatives

Related Products of 320734-35-8, 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. 320734-35-8, name is 7-Bromooxindole, This compound has unique chemical properties. The synthetic route is as follows.

To the suspension of VIb (200mg, 0.94 mmol) in water (5 mL) and sodium hydroxide (56mg, 1.41 mmol) was added dimethyl sulphate (178mg, 1.41 mmol) and the mixture was heated at 100 oC for lh. After the consumption of starting material, reaction mixture was cooled to 0 oC, added water and extracted with ethyl acetate. Organic layer was washed with brine, dried over sodium sulphate and evaporated under reduced pressure. So obtained crude was purified by column chromatography by using 10% ethyl acetate in pet-ether to get pure Vic (180 mg).

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

Reference:
Patent; BUGWORKS RESEARCH INDIA PVT LTD; PEER MOHAMED, Shahul Hameed; BHARATHAM, Nagakumar; KATAGIHALLIMATH, Nainesh; SHARMA, Sreevalli; NANDISHAIAH, Radha; (113 pag.)WO2017/199265; (2017); 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. 15861-23-1, name is Indoline-5-carbonitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 15861-23-1

tert-butyl 3-(5-cyanoindolin-1-yl)pyrrolidine-1-carboxylate To a solution of indoline-5-carbonitrile (110 mg, 0.75 mmol) in 2.5 mL of MeOH was added tert-butyl 3-oxopyrrolidine-1-carboxylate (166 mg, 0.90 mmol) and HOAc (0.11 mL, 1.88 mmol) subsequently. After stirring at room temperature for 10 minutes, NaCNBH3 (57 mg, 0.90 mmol) was added and the mixture was then stirred at ambient temperature for 2 days. The volatiles were removed under vacuum. The residue was diluted with EtOAc, then washed with 1 N NaOH solution and brine, dried over Na2SO4, and evaporated in vacuo to afford the crude title compound for the next step use without further purification.

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 15861-23-1.

Reference:
Patent; Su, Wei-Guo; Deng, Wei; Li, Jinshui; Ji, Jianguo; US2013/210831; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 1074-82-4, 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. 1074-82-4 name is Potassium 1,3-dioxoisoindolin-2-ide, 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.

To a solution of 1,5-dibromopentane (55.9 g, 243 mmol, 32.9 mL) in acetone (250 mL) was added (1,3-dioxoisoindolin-2-yl)potassium (15.0 g, 81.0 mmol) in portions over 30 minutes. The mixture was then stirred at rt for 30 minutes, and then heated to 60 C. and stirred for 15 hrs. On completion, the reaction mixture was filtered and concentrated in vacuo to give a residue. The residue was purified by silica gel chromatography (PE:EA=15:1 to 10:1) to give the title compound (20.0 g, 82% yield) as a white solid. LC-MS (ESI+) m/z 296.0 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Potassium 1,3-dioxoisoindolin-2-ide, and friends who are interested can also refer to it.

Reference:
Patent; Kymera Therapeutics, Inc.; Mainolfi, Nello; Ji, Nan; Kluge, Arthur F.; Weiss, Matthew M.; Zhang, Yi; (1443 pag.)US2019/192668; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 111992-61-1, 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. 111992-61-1, name is 2-(3-Bromo-2,2-dimethylpropyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

Step 3. A suspension of 3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (400 mg, 1.3 mmol, 1.00 equiv), 2-(3-bromo-2,2-dimethylpropyl)-2,3-dihydro-1H-isoindole-1,3-dione (570 mg, 1.95 mmol, 1.50 equiv) and cesium carbonate (847 mg, 2.60 mmol, 2.00 equiv) in NMP (50 mL) was stirred at 100 C for 12 h under nitrogen atmosphere. It was quenched with water (150 mL). The resulting solution was extracted with ethyl acetate (5 x 30 mL). The organic layers were combined, dried over sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column eluting with dichloromethane/methanol (10 /1). This resulted in 280 mg (41%) of 2-(2-[[4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-2-methylpropyl)-2,3-dihydro-1H-isoindole-1,3-dione as a yellow oil.

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

Reference:
Patent; PRINCIPIA BIOPHARMA INC.; BABLER, Martin; GERRITSEN, Mary E.; WO2014/22569; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-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. category: indolines-derivatives

General procedure: At the first, a mixture containing (10% mol) aimin base ligand and transition metal salts (10% mol) was prepared in 10 ml dichloromethan. Then a mixture of isatin derivatives (1 mmol) and (S)-proline (1.1 mmol), in 10 mL ethanol was added to mixture. After completion of the reaction (monitored by TLC), the reaction mixture was extracted with dichloromethane (15 mL). The combined organic layer dried over anhydrous MgSO4. The organic layer was concentrated in vacuum to furnish the products, which were recrystallized from ethanol.

The synthetic route of 5-Bromo-1-methylindoline-2,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Taghizadeh, Mohammad Javad; Javidan, Abdollah; Jadidi, Khosrow; Journal of the Korean Chemical Society; vol. 59; 3; (2015); p. 205 – 208;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 88150-75-8, name is Ethyl 4-(2-(1,3-dioxoisoindolin-2-yl)ethoxy)-3-oxobutanoate, 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. Quality Control of Ethyl 4-(2-(1,3-dioxoisoindolin-2-yl)ethoxy)-3-oxobutanoate

EXAMPLE 1 Ethyl 2-(o-chlorobenzylidene)-4-(2-phthalimidoethoxy)acetoacetate (Compound 3a) 300 g of ethyl 4-(2-(phthalimido)ethoxy)acetoacetate was mixed with 90 ml of 2-chlorobenzaldehyde and 140 ml of 2-propanol. The solution was agitated at 20-25 C. and the solution of 3.6 ml of piperidine in 40 ml of 2-propanol was added dropwise during 2 hours. The mixture was than stirred for 1 hour at the same temperature and 2 hours at 35-40 C. The mixture was acidified with 4.1 ml of acetic acid, 500 ml of 2-propanol was added and the solution was cooled to 0-5 C. Two layers are formed in the reaction mixture; the upper one was separated and the lower organic layer was again washed with 200 ml of 2-propanol. The organic layer, containing the desired product, was evaporated to dryness in order to remove the residual solvent. Yield: 350 g (84%), as the mixture of cis and trans isomers (6:4). Content of 2-chlorobenzaldehyde less than 5%.

The synthetic route of Ethyl 4-(2-(1,3-dioxoisoindolin-2-yl)ethoxy)-3-oxobutanoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Peters, Theodorus H. A.; Benneker, Franciscus B. G.; Slanina, Pavel; Bartl, Jiri; US2002/143046; (2002); A1;; ; Patent; Synthon BV; US6653481; (2003); B2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 4702-13-0, These common heterocyclic compound, 4702-13-0, name is N-Phthaloylglycine, 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 N-Phthaloylglycine (10.0 g, 48.7 mmol) in DCM (100 mL) was added oxalyl chloride (6.3 mL, 73.1 mmol) at r.t., followed by a drop of DMF. The reaction was stirred for 2 h and then concentrated to give compound 651 (10.8 g) as a yellow solid.

Statistics shows that N-Phthaloylglycine is playing an increasingly important role. we look forward to future research findings about 4702-13-0.

Reference:
Patent; HANGZHOU DAC BIOTECH CO. LTD; ZHAO, Robert Yongxin; YANG, Qingliang; HUANG, Yuanyuan; ZHAO, Linyao; GAI, Shun; YE, Hangbo; LEI, Jun; XU, Yifang; CAO, Mingjun; GUO, Huihui; JIA, Junxiang; TONG, Qianqian; LI, Wenjun; ZHOU, Xiaomai; XIE, Hongsheng; BAI, Lu; CAI, Xiang; ZHUO, Xiaotao; ZHANG, Xiuzheng; ZHENG, Jun; (424 pag.)WO2019/127607; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 114041-16-6, 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 114041-16-6 as follows.

A solution of 5,6-dimethoxyisoindoline 10e (0.08 g, 0.46 mmol) in acetic acid (0.92 mL) is stirred at room temperature. Sulfuryl chloride (0.11 mL, 1.4 mmol) is added drop-wise, and the resulting mixture is stirred at room temperature for 4 h. The reaction is concentrated under reduced pressure to give compound 10k as its HCl salt (0.130 g, quantitative yield) as a light-brown foam, m/z=248/250/252 [M+H]+.

According to the analysis of related databases, 114041-16-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Gladius Pharmaceuticals, Inc.; SUTTON, Larry D.; ZAMBONI, Robert; BUREAU, Patrick; HASSANPOUR, Avid; MAMANI LAPARRA, Laura; VIDAL, Marc; WOO, Simon; ZHOU, Nancy; KEENAN, Richard M.; (127 pag.)US2019/100534; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 169037-23-4, A common heterocyclic compound, 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, molecular formula is C9H4F3NO3, 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.

General procedure: 1M solution of phenylmagnesium bromide in THF (20.40mL, 20.40mmol) was added dropwise to a stirred ice-cold solution of isatin (1g, 6.80mmol) in anhydrous THF (20mL) that was kept under nitrogen. The reaction was stirred at room temperature for 2h and then quenched with a saturated aqueous solution of NH4Cl (20mL). Water was then added (30mL) and the aqueous phase was extracted twice with dichloromethane (2¡Á60mL). The organic phase was washed with brine and dried over anhydrous Na2SO4. The solvent was removed in vacuum and the crude was purified by crystallization from EtOAc/Hexane to afford 1 (1.18g, 77.1%) as a white powder.

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:
Article; Denoyelle, Severine; Chen, Ting; Yang, Hongwei; Chen, Limo; Zhang, Yingzhen; Halperin, Jose A.; Aktas, Bertal H.; Chorev, Michael; European Journal of Medicinal Chemistry; vol. 69; (2013); p. 537 – 553;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 2058-72-2,Some common heterocyclic compound, 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, molecular formula is C9H6BrNO2, 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.

General procedure: A septum-capped vial with a stirring bar was charged with the corresponding isatin(0.1 mmol), ester (0.2 mmol, 2.0 equiv.), catalyst and solvent (1 mL). The reactionmixture was conducted in setting temperature and monitored by TLC. The resultingreaction mixture was vapored in vacuum and the residue was purified by columnchromatography (Hexane/EtOAc = 8/1 to 4/1). The desired products were obtained ascolorless oil or white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-1-methylindoline-2,3-dione, its application will become more common.

Reference:
Article; Zhang, Xianhui; Zhou, Li; Mahmood, Qaiser; Zhao, Mengmeng; Wang, Xiaowu; Wang, Qinggang; Synlett; vol. 30; 5; (2019); p. 573 – 576;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem