Author: Jessica.F

Related Products of 22190-33-6, These common heterocyclic compound, 22190-33-6, name is 5-Bromoindoline, 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.

Step 2. tert-Butyl-5-bromoindoline-1-carboxylate (BI12) To a stirred solution of 5-bromo-indoline (3.0 g, 15 mmol) in acetonitrile (100 ml), was added DMAP (0.185 g, 1.522 mmol) and di-tert-butyl dicarbonate (3.98 g, 18.3 mmol) and the reaction was stirred at ambient temperature for 16 h. The reaction mixture was concentrated on reduced pressure to obtain a residue which was diluted with diethyl ether and washed with water and brine solution (2¡Á). The combined ether layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford the crude product as a off-white solid, which was used in the next step without further purification (3.0 g).

The synthetic route of 22190-33-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dow AgroSciences LLC; Lo, William C.; Hunter, James E.; Watson, Gerald B.; Patny, Akshay; Iyer, Pravin S.; Boruwa, Joshodeep; US9211280; (2015); B2;,
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Related Products of 6872-06-6, 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. 6872-06-6, name is 2-Methylindoline, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: The synthesis of 2-(6-(indolin-1 -yl)-6-oxohexyl)phthalimide 5.2.4 was performed following the report of Krasnov and co-workers ( see Krasnov et al., Mendeleev Commun. 25:412 (2015)): To a stirred solution of aniline (1 .0 equiv) and A/,A/-diethylaniline (1 .0 equiv) in 0.2 M dry CH2CI2was added a 0.2 M solution of acid chloride (1 .0 equiv) in dry CH2CI2dropwise over 10 min. After stirring at room temperature for 16 h, a 1 .0 N aq soln of HCI was added to the reaction mixture. After 30 min, the reactives were diluted with 20 ml. of EtOAc and washed with 2 c 20 ml. of water and 20 ml. of a 5% aq soln of NaHC03. The resulting organic phase was dried over Na2S04, filtered and the filtrate was concentrated in vacuo. The resulting residue was purified by MPLC to afford the product.

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

Reference:
Patent; THE BOARO OF TRUSTEES OF THE UNIVERSITY OF ILLINOIS; THE TRUSTEES OF INDIANA UNIVERSITY; DRIVER, Tom, G.; MACHADO, Roberto, F.; SU, Naijing; GUAN, Xinyu; MAZUMDAR, Wrickban; RATIA, Kira; HICKOK, Jason, Ralph; LOCKETT, Angelia, Denise; (159 pag.)WO2019/153007; (2019); A2;,
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Electric Literature of 16078-34-5, The chemical industry reduces the impact on the environment during synthesis 16078-34-5, name is 1-(2,3-Dihydro-1H-indol-5-yl)-ethanone, I believe this compound will play a more active role in future production and life.

Treat a 100 C. solution of 1-indolin-5-ylethanone (1.00 g, 6.02 mmol) in toluene (12 mL) with a solution of di-tert-butyl dicarbonate (1.97 g, 9.03 mmol) in toluene (12 mL) dropwise over 20 minutes. Continue heating the mixture for 30 minutes. Concentrate the reaction mixture. Purify by silica gel column chromatography with 15-35% (1:1 EtOAc:DCM) in hexanes to give the title compound (1.52 g, 97%) as a white solid. ES/MS (m/z): 262.0 (M+H).

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, 1-(2,3-Dihydro-1H-indol-5-yl)-ethanone, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Eli Lilly and Company; Bastian, Jolie Anne; Chen, Jiehao; Cohen, Jeffrey Daniel; Henry, James Robert; McMillen, William Thomas; Reaman, Bradley Earl; Rubio, Almudena; Sall, Daniel Jon; Zhao, Gaiying; (36 pag.)US2017/354641; (2017); A1;,
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Some common heterocyclic compound, 6341-92-0, name is 6-Chloroisatin, molecular formula is C8H4ClNO2, 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 6-Chloroisatin

Weigh6-chloroguanidine0.35g (0.0019mol),5-bromoindole anhydride0.48 g (0.0020 mol) was added to a 100 ml three-necked flask containing magnetons, and then 40 ml of chloroform was added to the three-necked flask.1.5 ml of triethylamine, heated to reflux in an oil bath at 80 C for 3 h,After the reaction is over, stop heating and wait for cooling.The crude product was obtained as a yellow solid powder by suction filtration.The product was washed 3 times with 10 ml of ethanol to obtain a pure product of a yellow solid powder.drying,Weigh 0.45 g and the yield was 66.2%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6341-92-0, its application will become more common.

Reference:
Patent; Northwest University; Wang Cuiling; Bai Xiao; Zhang Xiaobin; Liu Jianli; (16 pag.)CN110143964; (2019); A;,
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Related Products of 17630-75-0, 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. 17630-75-0, name is 5-Chloro-2-oxindole belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Step 1. 5-Chloroindoline-2-thione. To a solution of 5-chloroindolin-2-one (336 mg, 2 mmol) in toluene (12 ml) was added Lawesson’s Reagent (1.2 g, 3 mmol). The mixture was stirred at 105C for 3 hr. The resulting mixture was cooled and concentrated under reduced pressure. The residue was diluted with water (40 mL) and extracted with DCM (40 mL). Combined organic layers were dried over anhydrous Na2S04, and concentrated under reduced pressure. The residue was purified by flash column chromatography to give 5-chloroindoline-2-thione (270 mg, 75% yield) as a white solid. LC-MS: m/z: 184(M+H)+.

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

Reference:
Patent; THE GENERAL HOSPITAL CORPORATION; ZAHLER, Robert; WESTER, Ronald Thure; BRICKNER, Steven Joseph; WO2014/176258; (2014); A1;,
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Synthetic Route of 199328-10-4, These common heterocyclic compound, 199328-10-4, name is Methyl Oxindole-5-carboxylate, 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.

Step 1: A mixture of compound 1 (200 mg, 1.0 mmol) and HC1 (2.0 M in H20, 5 mL) was heated to 100C for overnight. The mixture was concentrated to get compound 2 (180 mg, 97%) as light yellow solid.

The synthetic route of 199328-10-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACETYLON PHARMACEUTICALS, INC.; VAN DUZER, John, H.; MAZITSCHEK, Ralph; WO2014/121062; (2014); A1;,
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Reference of 675109-26-9,Some common heterocyclic compound, 675109-26-9, name is 6-Bromoisoindolin-1-one, molecular formula is C8H6BrNO, 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.

Combine 6-bromo-2, 3-dihydro-isoindol-1-one (0.200 g, 0.94 mmol), bis- pinocalatodiboron (0.264 g, 1.04 mmol), palladium (II) acetate (16 mg, 0.07 mmol) and tricyclohexylphosphine (26 mg, 0.09 mmol) in a 50 mL flask. Add acetonitrile (10 mL) and cesium fluoride (0.428 g, 2.82 mmol); fit flask with condenser and heat in a 90 C oil bath for 1 hour. Cool to room temperature and add trifluoro-methanesulfonic acid 6- methoxy-1- [4- (2-piperidin-1-yl-ethoxy)-phenoxy]-naphthalen-2-yl ester (0.200 mg, 0.38 mmol), palladium (II) acetate (13 mg, 0.05 mmol) and tricyclohexylphosphine (20 mg, 0.07 mmol), cesium fluoride (0.172 g, 1.13 mmol) and acetonitrile (5 mL). Heat mixture in a 90 C oil bath for 1 hour. Cool reaction to room temperature and filter through celite and wash celite pad with ethyl acetate (60 mL). Concentrate the filtrate and pre-adsorb the crude product onto silica gel. Chromatograph the residue on a Si02 column eluting the material with methanol in dichloromethane (0 to 15%) to give 110 mg of the title compound (57 %).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Bromoisoindolin-1-one, its application will become more common.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/73205; (2005); A1;,
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Some common heterocyclic compound, 3485-84-5, name is N-Vinylphthalimide, molecular formula is C10H7NO2, 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. Formula: C10H7NO2

In a sealed tube under argon atmosphere, were introduced compound 4 (0.39g, 2.0mmol), DMF (5mL), triethylamine (1.2mL, 8mmol), palladium diacetate (22.5mg, 0.1mmol), tri(o-tolyl)-phosphine (61mg, 0.2mmol) and N-vinylphthalimide (0.52g, 3mmol). The mixture was stirred at 110C for 5h and then hydrolyzed. The formed solid was solubilized in CH2Cl2, washed with water and brine, dried over MgSO4 and evaporated under reduced pressure. The crude product was recrystallized from toluene to afford 5 as a brown solid (50% yield); mp 236C; 1H NMR (300MHz, DMSO-d6): delta 9.00 (s, 1H), 8.42 (d, J=15Hz, 1H), 7.92 (d, J=9.0Hz, 1H), 7.83-7.82 (m, 2H), 7.80-7.74 (m, 2H), 7.53 (dd, J=9.0, 2.8Hz, 1H), 7.46 (d, J=2.8Hz, 1H), 6.25 (d, J=15Hz, 1H), 3.88 (s, 3H); 13C NMR (75MHz, CD2Cl2): delta 165.2, 162.2, 159.5, 153.6, 145.1, 132.8, 132.1, 130.2, 126.5, 127.4, 123.7, 123.3, 100.6, 95.8, 55.8.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3485-84-5, its application will become more common.

Reference:
Article; Bolteau, Raphael; Caignard, Daniel H.; Delagrange, Philippe; Descamps, Florian; Ettaoussi, Mohamed; Melnyk, Patricia; Yous, Said; European Journal of Medicinal Chemistry; vol. 189; (2020);,
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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. 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 5-(Trifluoromethoxy)indoline-2,3-dione

Weigh 5-trifluoromethoxyBlush1.0g (0.0043mol),5-chloroindole anhydride 0.9g (0.0045mol) was added to a 100ml three-necked flask containing magnetons.Then add 40 ml of chloroform to the three-necked flask.1.5 ml of triethylamine, heated to reflux in an oil bath at 80 C for 3 h,After the reaction is over, stop heating and wait for cooling.The crude product was obtained as a yellow solid powder by suction filtration.The product was washed 3 times with 10 ml of ethanol.Obtaining a pure product yellow solid powder,drying,Weighing 1.12g,The yield was 70.9%.

The synthetic route of 169037-23-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Northwest University; Wang Cuiling; Bai Xiao; Zhang Xiaobin; Liu Jianli; (16 pag.)CN110143964; (2019); A;,
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Synthetic Route of 90725-50-1, These common heterocyclic compound, 90725-50-1, name is 6-Bromo-3-methylindolin-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.

[(2R)-2-(4-Iodophenyl)propyl][(methylethyl)sulfonyl]amine (0.295 g, 0.804 mmol) bis(pinacolate) diboron (0.224 g,0.882 mmol) PdCl2(dppf).CH2Cl2 (0.020 g, 0.024 mmol) and KOAc (0.0.276 g, 2.81 mmol) were combined and heated at 80 C. under nitrogen for 24 h. The mixture was allowed to cool to ambient temperature and 6-bromo-3-methyl-1,3-dihydro-1-indol-2-one (0.0.200 g, 0.885 mmol), PdCl2(dppf).CH2Cl2 (0.020 g, 0.024 mmol)), 2M Na2CO3 (2.0 mL, 5.0 mmol) respectively were added. The resulting mixture was heated and stirred at 80 C. overnight and worked up in a manner analogous to the procedure described in example 3 to provide the final title compound, 6-[4-((1R)-1-methyl-2-{[(methylethyl)sulfonyl]amino}ethyl)phenyl]-3-methylindolin-2-one, (0.050 g). MS: 387(M+1).

Statistics shows that 6-Bromo-3-methylindolin-2-one is playing an increasingly important role. we look forward to future research findings about 90725-50-1.

Reference:
Patent; Bender, David Michael; Forman, Scott Louis; Jones, Winton Dennis; Smith, Daryl Lynn; Zarrinmayeh, Hamideh; Zimmerman, Dennis Michael; US2003/225127; (2003); A1;,
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