Tag: M.W=100-200

Related Products of 20876-36-2, These common heterocyclic compound, 20876-36-2, name is 5-Aminoindolin-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.

To a solution of 5-amino oxindole (2 g, 13.5 mmol) in 80 ml of water/dioxane 3:1 was added sodium hydroxide 1N until obtaining pH 10 and then di-t-Butyl pyrocarbonate (3.5 g, 16.2 mmol). The reaction was stirred for 3 h maintaining pH 10. After extraction with 3*10 ml of ethyl acetate, the extracted were dried over sodium sulphate and evaporated obtaining 2.4 g of 5-t-Butoxycarbonylamino oxindole (71percent yield). 1 H-NMR (400 MHz, DMSO, T=45¡ã C.) 1.49 (s, 9H); 3.87 (s, 3H); 6.72 (d, J=8.4 Hz, 1H); 6.86 (dd, J=2.2 Hz, J=8.8 Hz, 1H); 7.12 (dd, J=1.8 Hz, J=8.4 Hz, 1H); 7.40 (d, J=8.8 Hz, 1H); 7.54 (d, J=2.2 Hz, 1H); 7.78 (d, J=1.8 Hz, 1H); 7.92 (s, 1H); 8.87 (bs, 1H); 9.38 (s, 1H); 10.25 (s, 1H); 11.8 (bs, 1H). FD-MS: 248 (100, [M]+); 191 (18, M-C4 H9!+); 147 (5, M-(CH3)3[COCO]+)

The synthetic route of 20876-36-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pharmacia & Upjohn S.p.A.; US5849710; (1998); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 2058-74-4, 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 2058-74-4 as follows.

General procedure: To a stirred mixture of 1-benzyl-1H-indole-2,3-dione (1a, 0.25 g,1.05 mmol), CuI (0.01 g, 0.05 mmol, 0.05 equiv), and phenylacetylene (2a, 0.11 g, 1.11 mmol, 1.05 equiv) in anhyd toluene (2 mL), DBU (0.032 g, 0.21 mmol, 0.2 equiv) was added at 25 C under a N2 atmosphere. Stirring was continued at this temperature until the starting material was completely consumed (TLC monitoring). After completion, the mixture was quenched with sat. aq NH4Cl (2mL) and extracted with EtOAc (2 ¡Á 5 mL). The combined organic layers were dried (anhyd Na2SO4) and evaporated under reduced pressure to dryness. The crude product thus obtained was purified by column chromatography (activated silica gel, 60-120 mesh, hexane-EtOAc) to afford pure 3aa as a white solid; yield: 0.35 g (97%); mp 177-179 C.

According to the analysis of related databases, 2058-74-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Chouhan, Mangilal; Senwar, Kishna Ram; Kumar, Kapil; Sharma, Ratnesh; Nair, Vipin A.; Synthesis; vol. 46; 2; (2014); p. 195 – 202;,
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. 16800-68-3, name is 1-Acetylindolin-3-one, This compound has unique chemical properties. The synthetic route is as follows., Formula: C10H9NO2

General procedure: 1a (35.0 mg, 0.2 mmol, 1 equiv.), tert-BuOK (22.4 mg, 0.2 mmol, 1.0 equiv.) were added to a Schlenk tube. Then 2 ml THF was added using a syringe. The reaction mixture was stirred 15min,and then added iodonium salt 2 (0.2 mmol, 1.0 eq). The reaction was stirred at 30C for 10 hours.After cooling to room temperature, the solvent was removed in vacuo and the residue was purifiedby silica gel using a proper eluent (EtOAc/Hexane) to afford the desired products

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 16800-68-3.

Reference:
Article; Zhang, Yanxia; Han, Jianwei; Liu, Zhen-Jiang; Synlett; vol. 26; 18; (2015); p. 2593 – 2597;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

3485-84-5, name is N-Vinylphthalimide, 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. Quality Control of N-Vinylphthalimide

Preparation 9 2-{2-[4-(2-Hydroxy-ethyl)-phenyl]-vinyl}-isoindole-1,3-dione To a solution of 2-(4-bromophenyl)ethanol (48.3 g) in acetonitrile (480 mL) was added diisopropylethylamine (46.6 g), N-vinylphthalimide (43.7 g) and tri-o-tolylphosphine (7.31 g) and the mixture was purged with nitrogen gas three times. Palladium acetate (2.7 g) was added and the mixture was stirred at 90 C. for 21 hr under nitrogen. The reaction was cooled and the precipitated product collected by filtration. The resulting solid was re-dissolved in dichloromethane and ethyl acetate and filtered through silica gel. The filtrate was concentrated in vacuo to give the title compound, 24 g. 1H NMR (400 MHz, CDCl3) delta=2.81-2.84 (t, 2H), 3.82-3.90 (t, 2H), 7.23-7.26 (d, 2H), 7.32-7.26 (d, 1H), 7.40-7.43 (d, 2H), 7.61-7.64 (d, 1H), 7.66-7.78 (d, 2H), 7.86-7.88 (d, 2H) ppm.

The synthetic route of 3485-84-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jones, Lyn Howard; Roberts, Dannielle Frances; Strang, Ross Sinclair; US2010/10040; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 6341-92-0, name is 6-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 6341-92-0, Recommanded Product: 6-Chloroisatin

Step 3: 6′-Chlorospiro[1,3-dioxane-2,3′-indol]-2′(1’H)-one A mixture of 6-chloroisatin (10.39 g, 57.2 mmol), 1,3-propanediol (10.74 mL, 143 mmol, 2.5 eq) and p-toluenesulfonic acid monohydrate (2.18 g, 11.4 mmol, 0.2 mol %) in benzene (IL) was heated to reflux under a Dean Stark Trap for 20 hr. Additional p-toluenesulfonic acid (5.44 g, 0.5 mol %) and 1,3-propanediol (5 mL) was added and the reaction was refluxed for an additional 4 hr then stirred at room temperature overnight. The reaction was concentrated and the residue was taken up in EtOAc, washed with sat. aq. NaHCO3 (3*), water (3*), dried over Na2SO4, filtered, and concentrated. The crude product was purified on Biotage KP silica gel eluding with 96/4 (CH2Cl2/CH3OH) to give an orange gummy solid (13.25 g, 97%) which was triturated with CH3OH (100 mL) to give the title compound as an orange colored solid (8.85 g, 64.6% yield). NMR (400 MHz, DMSO-d6): consistent. MS: (API-ES-) m/z 237/239 [M-H]1 chlorine pattern observed.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Chloroisatin, and friends who are interested can also refer to it.

Reference:
Patent; Wyeth; US2005/250798; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

340702-10-5, name is 6-Fluoroisoindolin-1-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. Recommanded Product: 340702-10-5

To a 0 C suspension of 6-fluoroisoindoline-l-one (8.0 g, 5.3 mmol) in concentrated H2S04 was added drop-wise a pre-cooled mixture of concentrated H2S04 (26 mL) and nitric acid (6 mL) while keeping the reaction mixture below 5 C. After addition, the reaction mixture was slowly warmed to room temperature during overnight. Ice (50 g) was added to the mixture and the solid was collected and dried, then washed with MTBE (50 mL) and ethyl acetate (50 mL) to give the desired product as a light yellow solid ( 5.1 g, 50%). MS: (ES) m/z calculated for C8H6FN203[M+H]+ 197.2, found 197.2.

The synthetic route of 340702-10-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHEMOCENTRYX, INC.; CHEN, Xi; DRAGOLI, Dean, R.; FAN, Junfa; KALISIAK, Jaroslaw; KRASINSKI, Antoni; LELETI, Manmohan, Reddy; MALI, Venkat; MCMAHON, Jeffrey; SINGH, Rajinder; TANAKA, Hiroko; YANG, Ju; YU, Chao; ZHANG, Penglie; (198 pag.)WO2017/87607; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 19727-83-4, name is 6-Nitroindoline, molecular formula is C8H8N2O2, 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. Recommanded Product: 19727-83-4

5-Trifluoromethyl-7-pyridono[5,6-e]indoline (Compound 419, structure 49A of Scheme XLV, where R1 =trifluoromethyl, R2 =H) 6-Aminoindoline A solution of 6-nitroindoline (1 g, 6.1 mmol) in 50 mL of ethyl acetate was hydrogenated under an atmosphere of hydrogen with Pd-C 10% (100 mg) at rt for 3 h. Filtration over celite afforded 1.0 g (98%) of 6-aminoindoline. Data for 6-aminoindoline: 1 H NMR (400 MHz, CDCl3) 7.40 (d, J=7.4, 1H), 6.05 (d, J=2.0, 1H), 6.03 (d, J=7.5, 1H), 3.67 (bs, 1H), 3.49 (t, J=8.1, 2H), 3.48 (bs, 2H), 2.90 (t, J=8.2, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 19727-83-4, its application will become more common.

Reference:
Patent; Ligand Pharmaceuticals Incorporated; US5688810; (1997); A;,
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. 39603-24-2, name is 5,7-Dimethylindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Formula: C10H9NO2

General procedure: A mixture of phenylhydrazine (1 mmol), 3-aminocrotononitrile (1 mmol), and InCl3 (0.1 mmol) in water (10 ml) was added to isatin (1 mmol) and the reaction mixture heated under reflux at 100 C for 10 min. After completion of the reaction (TLC), the reaction mixture was cooled to room temperature; the precipitate was filtered off and washed with methanol to obtain pure 13 as a colorless solid. Spectroscopic data for all the compounds are given below.

According to the analysis of related databases, 39603-24-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Balamurugan, Kamaraj; Perumal, Subbu; Menendez, J. Carlos; Tetrahedron; vol. 67; 18; (2011); p. 3201 – 3208;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem