Category: indolines-derivatives

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 100487-74-9 as follows. Synthetic Route of 100487-74-9

To the mixture of 6-chloro-5-fluoro-1,3-dihydro-indol-2-one (500 mg, 2.7 mmol) and 2-(4-Chloro-2-formyl-phenoxy)-2-ethyl-butyric acid methyl ester (844 mg, 2.97 mmol) (CGENETECH) in methanol (5 mL) was added pyrrolidine (95 mg, 1.35 mmol) dropwise. The mixture was then heated at 70 C. for 1 h. After cooled to room temperature, the mixture was partitioned between EtOAc and diluted HCl. The organic phase was washed with water, brine, dried over anhydrous Na2SO4 and concentrated to give the crude product as a red-yellow solid, which was used for the next step reaction without further purification.

Future efforts will undeniably focus on the diversification of the new catalytic transformations. These may comprise an expansion of the substrate scope from aromatic and heteroaromatic compounds to other hydrocarbons. Keep reading other articles of 100487-74-9.

Reference:
Patent; Chen, Li; Han, Xingchun; Wang, Lisha; Wang, Min; Yang, Song; Zhang, Zhuming; US2010/190814; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 3484-35-3, name is 5-Methylindolin-2-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 3484-35-3, 3484-35-3

General procedure: To a mixture of oxindole (3a-f, 0.3mmol), 1-alkyl-1H benzo[d]imidazole-2-carbaldehydes (7a-e, 0.33mmol) in ethanol (2mL), was added catalytic amount of piperidine. The reaction mixture was stirred at reflux until complete consumption of the oxindole observed by TLC. After cooling, the precipitate was filtered, washed with cold ethanol, and dried in air to furnish pure (E)-benzo[d]imidazol-2-yl)methylene)indolin-2-ones 8a-z orange/yellow solids in moderate to good yields. Compounds 8c, 8f, 8i, 8l and 8o did not precipitated out from ethanol, were purified by column chromatography with silica gel (60-120) by using ethyl acetate:hexane (2:8 to 3:7). 4.1.1.14 (E)-3-((1-Ethyl-1H-benzo[d]imidazol-2-yl)methylene)-5-methylindolin-2-one (8n) Orange solid, Yield 84%; mp: 274-276 C; FT-IR: (cm-1): 3166, 3067, 2980, 1704, 1615, 1323, 813, 742;1H NMR (300 MHz, DMSO-d6): delta 10.20 (brs, 1H, NH), 9.22 (s, 1H, Ar-H), 7.87 (d, J = 7.2 Hz, 1H, Ar-H), 7.65-7.58 (m, 1H, Ar-H), 7.56 (s, 1H, C=CH), 7.51-7.28 (m, 2H, Ar-H), 7.09 (d, J = 7.9 Hz, 1H, Ar-H), 6.78 (d, J = 7.9 Hz, 1H, Ar-H), 4.54-4.41 (m, 2H, CH2), 2.38 (s, 3H, CH3), 1.50 (t, J = 7.3 Hz, 3H, CH3); 13C NMR (125 MHz, DMSO-d6): delta 168.9, 146.8, 142.9, 141.3, 134.6, 131.7, 131.2, 129.9, 128.6, 124.1, 122.9, 121.1, 119.8, 117.1, 110.6, 109.3, 38.4, 21.0, 15.7; HRMS (ESI): m/z calcd for C19H18N3O 304.1450, found 304.1438 [M+H]+; Purity: 98.7%.

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 5-Methylindolin-2-one.

Reference:
Article; Sharma, Pankaj; Thummuri, Dinesh; Reddy, T. Srinivasa; Senwar, Kishna Ram; Naidu; Srinivasulu, Gannoju; Bharghava, Suresh K.; Shankaraiah, Nagula; European Journal of Medicinal Chemistry; vol. 122; (2016); p. 584 – 600;,
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Related Products of 141452-01-9, Researchers are common within chemical engineering and are often tasked with creating and developing new chemical techniques, frequently combining other advanced and emerging scientific areas.

A solution of methyl indoline-5-carboxylate (200 mg, 1.13 mmol) in tetrahydrofuran (10 ml.) was cooled in an ice-water bath for 5 minutes. Sodium hydride (45.15 mg, 1.13 mmol) in tetrahydrofuran (2 ml.) was added drop wise and the reaction was allowed to stir under cooling for 20 minutes before the dropwise addition of acetyl chloride (0.08 ml_, 1.13 mmol). The reaction mixture was stirred for 30 minutes. The reaction mixture was removed from the ice-water bath and allowed to warm to ambient temperature. After 1 hour the reaction was added dropwise to a saturated NH4CI solution and extracted with ethyl acetate three times. The organics were combined, dried over anhydrous MgS04, filtered to remove the solids, and concentrated under reduced pressure to give methyl 1 -acetylindoline-5- carboxylate as an off-white solid (235 mg, 1.07 mmol, 95%). LCMS: MS m/z 220.1 [M+H]+; 1H NMR (400 MHz, DMSO) d 8.09 (d, J = 8.9 Hz, 1H), 7.79 (d, J = 7.6 Hz, 2H), 4.14 (t, J = 8.6 Hz, 2H), 3.81 (s, 3H), 3.17 (t, J = 8.6 Hz, 2H), 2.18 (s, 3H).

We very much hope you enjoy reading the articles and that you will join us to present your own research about Methyl indoline-5-carboxylate.

Reference:
Patent; UCL BUSINESS LTD; FISH, Paul, Vincent; MAHY, William; WILLIS, Nicky, John; WOODWARD, Hannah; ATKINSON, Benjamin, N; BAYLE, Elliott, D; SIPTHORP, James; JONES, Edith, Yvonne; ZHAO, Yuguang; VECCHIA, Luca; RUZA, Reinis, Reinholds; (208 pag.)WO2020/43866; (2020); A1;,
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Electric Literature of 21544-81-0, 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 21544-81-0 as follows.

A solution of 3,5-dimethoxyaniline (199 g, 1.30 mol) in ether (5.0 L) in a 5 L 3-necked flask was cooled to 0C. HCI gas (227 g) was bubbled through the solution over 45 min. After 45 min at 10C, the mixture was filtered, washed with isopropylacetate (4 L), and dried overnight on high vacuum at 45C to give the hydrochloride (242.3 g, 98%), as a white solid. A mixture of the hydrochloride above (20 g, 0.105 mol) and oxalyl chloride (33 mL) in a 3-necked flask equipped with a reflux condenser was heated for 2 h with stirring (170C external temperature), and the oxalyl chloride was distilled from the reaction mixture. The flask was cooled to 0C and methanol (40 mL) was added. The reaction mixture was heated to reflux for 45 min, filtered while hot, and washed with methanol (80 mL) to give the 4,6-dimethoxyisatin (17.2 g, 79%) as a yellow-green solid. To a heated solution (external temp 70C) of the isatin (162 g, 0.78 mol) in aqueous NaOH (40%, 1.5 L) was added H2O2 (35%, 405 mL) slowly over 2 h. After the addition of each portion of H2O2, the internal reaction temperature (initially 64C) increased (to a maximum temp of 80C). After the addition was complete, the foaming reaction mixture was then stirred for an additional 2 h at 70C, and the mixture was allowed to stir overnight while cooling to RT. The mixture was heated to 70C. Additional H2O2 (75 mL) was added, and the mixture was stirred at 70C for a further 2 h until the reaction was complete. After cooling to 10C (bath temperature), aqueous Na2S2O3 (150 mL, saturated) was added. The mixture was brought to pH 8 with HCI (37%, 1.6 L) and pH 6 with acetic acid (glacial, 75 mL), without allowing the reaction mixture to warm to greater than 40C. Filtration of the reaction mixture and washing with water (4 L) gave the expected amino acid as a tan solid (83.7 g, 55%). To a solution of the amino acid (82.7 g, 0.42 mol) in anhydrous THF (4.2 L) was added EDCI (89.2 g, 0.48 mol), HOBT (65 g, 0.48 rnol), and NMM (51.3 mL), and the mixture was allowed to stir at RT for 3 h. Aqueous NH3 (83 mL, 50%) was added, and the mixture was stirred at RT for 16 h. Water (1.25 L) was added, and the mixture was extracted with DCM (2×250 mL). The combined extracts were then washed with water (2×500 mL). Concentration, formation of a slurry with ether (550 mL), filtration, and drying under high vacuum gave 2-amino-4,6-dimethoxybenzamide (46.7 g,57%) as a brown solid. [0111] 2-Amino-4,6-dimethoxy-benzamide (1.06 g, 5.4 mmol), 3,5-dimethyl- 4-hydroxybenzaldehyde (0.810 g, 5.4 mmol), K2CO3 (0.747 g, 5.4 mmol) and I2 (1.645 g, 6.5 mmol) were mixed in DMF (20 ml_) and the reaction mixture was heated at 80C for 12 h. It was cooled to RT and poured into crushed ice. The solid was collected and purified by column chromatography to give 2-(4-hydroxy- 3,5-dimethylphenyl)-5,7-dimethoxyquinazolin-4<3H)-one (0.9 g, 51%) as a white solid. Selected data: MP 291-293C. We very much hope you enjoy reading the articles and that you will join us to present your own research about 4,6-Dimethoxyindoline-2,3-dione. Reference:
Patent; Resverlogix Corp.; WO2008/92231; (2008); 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. 20870-78-4, name is 5-Bromoindolin-2-one, A new synthetic method of this compound is introduced below., Application In Synthesis of 5-Bromoindolin-2-one

A mixture of 28b (513mg, 2.42mmol), 4,4,5,5-tetramethyl-2-(4,4,5,5- tetramethyl (l,3,2-dioxaborolan-2-yl))-l ,3,2-dioxaborolane (716mg, 2.82mmol) and KOAc (878mg, 8.95mmol) in dioxane (2OmL) was purged with nitrogen for lOmin, then added Pd(dppf)Cl2. CH2Cl2 (108mg, 0.13mmol). The resulting mixture was stirred at 800C overnight and evaporated. The residue was dissolved in ethyl acetate and filtrated. The filtrate was washed with brine (15mLchi2), dried over Na2SO4 and concentrated. The residue was purified by column chromatography (EA: PE =4:1) to afford 28c (470mg, 75%).

We are continuing to develop the new Research Structures and WebCSD systems in response to feedback from you, our user community, so we would love to hear what you think about the enhanced search functionality and any suggestions you might have about 20870-78-4.

Reference:
Patent; XCOVERY, INC.; WO2008/88881; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 52537-00-5, The prevalence of solvent effects in heterogeneous catalysis has motivated developing quantitative kinetic, spectroscopic, and theoretical assessments of solvent structures and their interactions with reaction intermediates and transition states.

EXAMPLE 208b Preparation of rac-6,6′-Dichloro-3′-(3-chloro-benzyl)-2,3,1′,3′-tetrahydro-[1,3′]biindolyl-2′-one The mixture of rac-3-bromo-6-chloro-3-(3-chloro-benzyl)-1,3-dihydro-indol-2-one (100 mg, 0.27 mmol) (from example 1c supra), 6-chloro-2,3-dihydro-1H-indole (62 mg, 0.45 mmol) and K2CO3 (110 mg, 0.80 mmol) in DMF (1 mL) was stirred at room temperature overnight. Then water (10 mL) was added and the desired product was precipitated out. The crude product was purified by prep-HPLC to give 55 mg rac-6,6′-Dichloro-3′-(3-chloro-benzyl)-2,3,1′,3′-tetrahydro-[1,3′]biindolyl-2′-one. MS: [M+H]+=443

The design and synthesis of related molecules that are more effective, more selective, and less toxic than aspirin are important objectives of biomedical research.Keep reading other articles of 6-Chloro-2,3-dihydro-1H-indole.

Reference:
Patent; Chen, Li; Yang, Song; Zhang, Jing; Zhang, Zhuming; US2008/81810; (2008); A1;,
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HPLC of Formula: C8H9N,The dynamic chemical diversity of the numerous elements, ions and molecules that constitute the basis of life provides wide challenges and opportunities for research.

The above compound was prepared as follows using General Procedure G9. lsoindoline (130 mg, 1 mmol) was added to a solution of 3-chloro-4,6-dimethoxy-2- methylbenzoic acid (compound A in general procedure G9, and prepared via the method reported by Clevenger et al. Organic Letters (2004), 6(24), p4459)) (200 mg, 0.87 mmole), diisopropylethyl amine (0.8 mL, 4.5 mmol), and O-(7-azabenzotriazol-1 -yl)-N,N,N’,N’- tetramethyluronium phosphorus pentafloride (HATU) (380 mg, 1 mmol) in 4 mL of DMF under a nitrogen atmosphere. The reaction was allowed to stir at room temperature for 12 hours. Saturated NaHCO3 (30 mL) was added to the reaction mixture to quench the reaction. EtOAc EPO (2 x 50 ml.) was then added to extract the aqueous solution. Dry EtOAc layer over Na2SO4. The Na2SO4 was filtered off and the filtrate was evaporated to give a brown oil residue. The residue was purified by silica gel chromatography (gradient elution 45 ?50% EtOAc in hexanes) to give the desired intermediate product (3-chloro-4,6-dimethoxy-2- methylphenyl)(isoindolin-2-yl)methanone (265 mg, 92% yield). 1H NMR (400 MHz, DMS0-D6) delta ppm 2.18 (s, 3 H) 3.81 (s, 3 H) 3.92 (s, 3 H) 4.39 (d, J=7.07 Hz, 2 H) 4.80 (s, 2 H) 6.76 (s, 1 H) 7.17 – 7.35 (m, 3 H) 7.38 (d, J=7.07 Hz, 1 H): Anal. Calcd for C18H18CINO3: C, 65.16; H, 5.47; N, 4.22. Found: C, 65.05; H, 5.48; N, 4.22.

We very much hope you enjoy reading the articles and that you will join us to present your own research about Isoindoline.

Reference:
Patent; PFIZER INC.; WO2006/117669; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Recommanded Product: tert-Butyl 4-bromoisoindoline-2-carboxylate, Chemistry built the modern world, from the materials that make up the everyday objects around us, the batteries in our devices and cleaning products that help to maintain sanitation.

A mixture of tert-butyl 4-bromoisoindoline-2-carboxylate (1.70 g, 5.70 mmol),4,4,4?,4?,5 ,5 ,5 ?,S ?-octamethyl-2,2?-bi(1 ,3 ,2-dioxaborolane) (1.74 g, 6.84 mmol), potassiumacetate (1.68 g, 17.1 mmol), and PdC12(dppf) DCM adduct (0.466 g, 0.570 mmol) in 1,4-dioxane (25 mL) was bubbled with nitrogen and stirred at 80 C overnight. The mixture was cooled to room temperature, diluted with EtOAc, washed with water, dried and concentrated. The residue was subjected to colunm chromatography on silica gel, eluting with EtOAc-hexanes (gradient from 0-30%), to provide tert-butyl 4-(4,4,5 ,5 -tetramethyl5 1 ,3,2-dioxaborolan-2-yl)isoindoline-2-carboxylate as a white solid (1.50 g, 76% yield).

As always, wish you can browse a selection of our May HOT articles below about tert-Butyl 4-bromoisoindoline-2-carboxylate.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; AHMAD, Saleem; BATT, Douglas G.; LIU, Qingjie; MACOR, John E.; TINO, Joseph A.; WATTERSON, Scott Hunter; NAIR, Satheesh Kesavan; MAISHAL, Tarun Kumar; (247 pag.)WO2016/65236; (2016); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

496-12-8,When developing chemical systems it’s of course important to gain a deep understanding of the chemical reaction process.

Triethylamine (0.33 ml, 2.37 mmol) and isoindoline (0.27 ml, 2.38 mmol) were added in turn to a solution of methyl ester of 5-chloro-2-trifluoromethanesulfonyloxy-3-nitrobenzoic acid (820 mg, 2.25 mmol) in dimethyl sulfoxide (5 ml) and the mixture was stirred at room temperature for 1 hr. The reaction mixture was cooled with ice and ice water (50 ml) was added thereto. The mixture was stirred and the precipitates were filtered, washed with water and dried. The resultant yellow crystals were purified by column chromatography on silica gel (n-hexane/ethyl acetate = 15) to give methyl ester of 5-chloro-2-(1,2,3,4-tetrahydroisoquinolinio)-3-nitrobenzoic acid (608 mg, 81 %) as yellow crystals. m.p.: 114 – 115 C; IR (Nujol): 1743, 1705, 1603, 1589, 1529, 1503 cm-1; APCI-MS m/z: 333[M+H]+.

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 496-12-8.

Reference:
Patent; Endo, Hitoshi; EP1481965; (2004); A1;,
Indoline – Wikipedia,
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Healthcare careers for chemists are once again largely based in laboratories, although increasingly there is opportunity to work at the point of care, helping with patient investigation., Reference of 56341-37-8

EXAMPLE 37a; Preparation of intermediate E/Z-4-[4-bromo-2-(6-chloro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-phenoxy]-piperidine-1-carboxylic acid tert-butyl ester; To a mixture of 6-chlorooxindole (4.58 g, 20 mmol) and 4-(4-bromo-2-formyl-phenoxy)-piperidine-1-carboxylic acid tert-butyl ester (10 g, 26 mmol) in methanol (50 mL) was added piperidine (2.56 mL, 26 mmol) dropwise. The mixture was then heated at 100 C. for 3 h. After cooled to 4 C., the mixture was filtered and the precipitate was collected, dried to give the title compound as a bright yellow solid (12.4 g, 90%).

Future efforts will undeniably focus on the diversification of the new catalytic transformations. These may comprise an expansion of the substrate scope from aromatic and heteroaromatic compounds to other hydrocarbons. Keep reading other articles of 56341-37-8.

Reference:
Patent; Chen, Li; Han, Xingchun; He, Yun; Yang, Song; Zhang, Zhuming; US2009/163512; (2009); A1;,
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Indoline | C8H9N – PubChem