Tag: M.W=100-200

Application of 496-12-8, 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. 496-12-8, name is Isoindoline, This compound has unique chemical properties. The synthetic route is as follows.

3-lodo-4-methylbenzoic acid (262 mg, 1.0 mmol), isoindoline (284 uL, 1.5 mmol), and triethylamine (420 uL, 3.0 mmol) were dissolved in 10 ml. Of CH2CI2 and treated with HOBt (203 mg, 1.5 mmol) and EDC (288 mg, 1.5 mmol). The reaction were stirred at room temperature overnight. The reaction mixture was concentrated, diluted with EtOAc, and washed with water, 1 N HCI, and brine. The organic layer was dried (MgSO4), filtered, and concentrated. The crude residue was purified by flash chromatography on silica gel (CH2CI2/Et0Ac) to yield 301 mg (83%) of the product as a tan solid. MS (+ESI): m/z 363.9 [M+H]+.

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

Reference:
Patent; WYETH LLC; LI, David, Zenan; O’NEIL, Steven, Victor; SPRINGER, Dane, Mark; ZEGARELLI, Benjamin, Miller; WO2010/124047; (2010); A1;,
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Synthetic Route of 16800-68-3, These common heterocyclic compound, 16800-68-3, name is 1-Acetylindolin-3-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.

General procedure: In an oven dried round-bottomed flask, a solution of the squaramide catalyst I (2 mol%) and 1-acetylindolin-3-one 1 (0.4 mmol) in CH2Cl2(1.0 mL) was stirred at r.t. After 5 min, the o-formyl-(E)-beta-nitrostyrene2 (0.48 mmol) was added and the stirring was continued until the complete consumption of the reactants was observed by TLC.Then the crude mixture was purified by flash chromatography on silicagel using a gradient of n-hexane-EtOAc (9:1 to 1:1) to afford the desired product 3.

Statistics shows that 1-Acetylindolin-3-one is playing an increasingly important role. we look forward to future research findings about 16800-68-3.

Reference:
Article; Mahajan, Suruchi; Chauhan, Pankaj; Loh, Charles C. J.; Uzungelis, Server; Raabe, Gerhard; Enders, Dieter; Synthesis; vol. 47; 7; (2015); p. 1024 – 1031;,
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These common heterocyclic compound, 14192-26-8, name is Methyl 2-oxoindoline-6-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. SDS of cas: 14192-26-8

To a solution of methyl 2-oxoindoline-6-carboxylate (17.6 g) in DMF (260 ml) was added Mel (26.1 g) followed by NaH (3.68 g) keeping the temperature at 22 C. After 30 min a second portion of NaH (1.84 g) was added followed after 1 h by a third portion (1.84 g) and stirring was continued at 22 C for 16 h. Water (7 ml) followed by sodium hydroxide (34.5 g) were added and stirring was continued at 45 C for 1 h and at 22 C for 16 h. The mixture was partitioned between TBME and water, the pH of the aqueous layer was adjusted to 3 using aqueous hydrochloric acid (25%) and extracted with dichloromethane. The organic layere was dried and evaporated to give the crude title compound (17.9 g, 95%) as a red solid, which was used without further purification. MS (ESI, m/z): 204.2 [(M-H)”].

The synthetic route of Methyl 2-oxoindoline-6-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HILPERT, Hans; KOLCZEWSKI, Sabine; LIMBERG, Anja; STOLL, Theodor; WO2015/177110; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 59-48-3, name is Indolin-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 59-48-3, Formula: C8H7NO

Concentrated nitric acid (9.31 g, 0.096 mol) was added in drops over 60 min and at 0 C. to a solution of indolin-2-one (13.3 g, 0.100 mol) in concentrated sulfuric acid (67 mL), and the resultant dark-brown solution was then stirred at this temperature for 1 h. The reaction mixture was then poured over ice and sucked away. The residue was washed again with water and dried, then recrystallized from isopropanol. 5-nitroindolin-2-one in the form of golden, shiny sheets was obtained (12.28 g, 69%). fp: >300 C. 1HNMR (300 MHz, d6-DMSO): delta=3.61 (s, 2H, H2), 6.97 (d, 1H, H7), 8.05 (d, 1H, H6), 8.05 (s, 1H, H4), 8.15 (d, 1H, H6), 11.03 (bs, 1H, NH). 13C NMR (100 MHz, DMSO): 35.9 (C2), 109.2 (C7), 120.3 (C4), 125.1 (C6), 127.2 (C9), 142.0 (C5), 150.6 (C8), 177.0 (C2)

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Reference:
Patent; Henkel AG & Co. KGaA; Gebert-Schwarzwaelder, Antje; Giesa, Helmut; Schoenebeck, Jan-Michael; (23 pag.)US2017/165166; (2017); A1;,
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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. 14192-26-8, name is Methyl 2-oxoindoline-6-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of Methyl 2-oxoindoline-6-carboxylate

Intermediate Ia (4Og) is dissolved in methanol (40OmL) and IM NaOH solution (420 mL) is added. The mixture is heated under reflux for 3 hours. The reaction is then neutralized with IM HCl. The methanol is then removed under reduced pressure and water is added EPO until precipitation commenced. The precipitate is collected via filtration, washed with water and dried under reduced pressure to yield the desired intermediate 2a (37g)

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 14192-26-8.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG; WO2006/64044; (2006); A1;,
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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. 39755-95-8, name is 5-Methoxyisatin, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 5-Methoxyisatin

Preparation of 5-methoxy-2-(1 -methyl-1 H-pyrazol-4-yl)-indole-3-carbaldehyde; 5-Methoxy isatin (0.2 g, 1.1 mmol, 1 eq.) was dissolved in hydrazine hydrate (1.2 ml_, 38 mmol, 34 eq.) and refluxed for 15 minutes. The reaction mixture was poured into cold water and extracted with EtOAc. The combined organic extracts were dried on Na2SO4. The solvent was evaporated to afford crude 5-methoxy-1 ,3-dihydro-indol-2-one that was purified by silica gel column chromatography (eluent: hexane/EtOAc from 10:0 to 6:4). Yield: 27%. MS (m/z): 164.2 (MH+).Phosphorous oxybromide (0.35 ml_, 3.1 mmol, 2.5 eq.) was added drop wise to a solution of DMF (0.3 ml_, 3.7 mmol, 3 eq.) in dry methylene chloride at 00C. The mixture was stirred at 00C for 30 minutes, then a solution of 5-methoxy-1 ,3-dihydro-indol-2-one (0.2 g, 1.2 mmol, 1 eq.) in dry methylene chloride (2 ml_) was added and the mixture was refluxed for 3 hours. The solution was neutralized with solid NaHCO3 and extracted with methylene chloride. The organic layer was dried on Na2SO4 and evaporated under reduced pressure. The crude mixture was purified by silica gel column chromatography (eluent: hexane/AcOEt 6:4 to 4:6) to give pure 2-bromo-5-methoxy-indole-3-carbaldehyde. Yield: 45%. MS (m/z): 254.1 (MH+). A stirred solution of 2-bromo-5-methoxy-indole-3-carbaldehyde (2.0 g, 7.9 mmol, 1 eq.) in DME (2 ml_) was deoxygenated by bubbling argon for 10 minutes at rt. Pd(PPh3)4 (0.9 g, 0.8 mmol, 0.1 eq.) was added followed by a solution of 1-methyl-4-(4,4,5,5-tetramethyl- [1 ,3,2]dioxaborolan-2-yl)-1 H-pyrazole (2.4 g, 1 1.63 mmol, 1.48 eq.) in ethanol (2.5 ml_). 2M Na2CO3 (33 ml_, 8.5 eq.) was also deoxygenated with argon and added. The resulting mixture was heated at 78C for 18 hours. The reaction mixture was cooled to room temperature, quenched with water, and extracted with methylene chloride. Organic layer was dried on anhydrous Na2SO4 and evaporated under reduced pressure to give the crude product 1f. Yield: 89%. MS (m/z): 256.1 (MH+).

According to the analysis of related databases, 39755-95-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; WYETH LLC; AYRAL-KALOUSTIAN, Semiramis; MANSOUR, Tarek Suhayl; TSOU, Hwei-Ru; ZHANG, Nan; VENKATESAN, Aranapakam M.; DI, Li; KERNS, Edward H.; WO2010/30727; (2010); A1;,
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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. 3485-84-5, name is N-Vinylphthalimide, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C10H7NO2

A 20-mL, microwave reaction vessel was charged with (3-bromopyridin-4-yl)-(4-(trifluoro methyl)phenyl)methanol (2.0 g, 6.02 mmol), 2-vinylisoindoline-1,3-dione (1.16 g, 6.68 mmol), 2-(dicyclohexylphosphino)biphenyl (0.211 g, 0.60 mmol), Pd(dba)2 (0.176 g, 0.30 mmol), NEt3 (1.0 mL, 7.23 mmol), and DMF. The mixture was purged with argon and heated in microwave synthesizer at 150 C. for 1 h. The reaction mixture was partitioned between water and EtOAc. The EtOAc layer was separated and aqueous layer was extracted again with EtOAc. The combined organic layers were washed with saturated NaHCO3, dried over Na2SO4, filtered, and concentrated in vacuo. The brown residue was triturated with DCM, the resulting precipitate was collected by filtration to afford the title compound as an ivory colored solid. 1H NMR (400 MHz, CDCl3): delta 8.70 (s, 1H), 8.58 (d, J= 5.1 Hz, 1H), 7.92-7.95 (m, 2H), 7.79-7.7.84 (m, 3H), 7.55-7.64 (m, 5H), 7.24 (s, 0.5H), 7.19 (s, 0.5H), 2.71 (d, J= 3.4 Hz, 1H).

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 3485-84-5.

Reference:
Patent; Nishimura, Nobuko; Norman, Mark H.; Tamayo, Nuria; Tang, Phi; Bo, Yunxin Y.; US2009/82358; (2009); A1;,
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Electric Literature of 3484-35-3,Some common heterocyclic compound, 3484-35-3, name is 5-Methylindolin-2-one, molecular formula is C9H9NO, 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: The appropriate aldehyde (1 equiv) was added to EtOH (3 mL/0.2 mmol) and the mixture was stirred until complete solution. Theoxindole (1 equiv) and piperidine (0.1 equiv) were added, and themixture was heated to 90C for 3-7 h, and cooled. The resultingprecipitatewas filtered, washed with cold ethanol and dried to givethe pure compound. If necessary, additional recrystallization inethanol was applied to obtain the pure product.

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

Reference:
Article; Delong, Wang; Lanying, Wang; Yongling, Wu; Shuang, Song; Juntao, Feng; Xing, Zhang; European Journal of Medicinal Chemistry; vol. 130; (2017); p. 286 – 307;,
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Related Products of 603-62-3, 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 603-62-3 as follows.

General procedure: A mixture of the appropriate thiol (6 mmol), 3-nitrophthalimide(4 mmol) and K2CO3 (10 mmol) in 20 mL acetone was heated underreflux for 24 h. The reaction was cooled to room temperature anddiluted with 150 mL water. The mixture was subsequently acidifiedto pH 2 with 6 N HCl. The resulting precipitate was collectedby filtration and dried at 50 C [19].

According to the analysis of related databases, 603-62-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Van Der Walt, Mietha M.; Terre’Blanche, Gisella; Petzer, Anel; Petzer, Jacobus P.; Bioorganic Chemistry; vol. 59; (2015); p. 117 – 123;,
Indoline – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 17564-64-6, name is 2-(Chloromethyl)isoindoline-1,3-dione, 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 17564-64-6, COA of Formula: C9H6ClNO2

General procedure: The initial carbonyl compound (50 mmol) was dissolved/suspended in ethanol (50 mL) and magnetically stirred with thiosemicarbazide (50 mmol) and catalytic amounts of acetic acid for 8-24 h at room temperature. The obtained thiosemicarbazone was filtered, washed with appropriate solvent (n-hexane, petroleumether or diethyl ether) and dried under vacuum. The intermediate thiosemicarbazone (50 mmol) reacted with ethyl bromoacetate (50 mmol), in methanol (50 mL) and sodium acetate (50 mmol) at room temperature under magnetic stirring for 24 h. The resulting 4-thiazolidinone was poured on ice, filtered or extracted with chloroform (3 x 100 mL) and purified by column chromatography (SiO2, ethyl acetate/n-hexane). Then, the obtained thiazolidinone (50 mmol) was dissolved/suspended in 50 mL of anhydrous acetone in the presence of anhydrous potassium carbonate (50 mmol), and reacted with equimolar amounts of 4-nitrobenzyl bromide, 1-(chloromethyl)naphthalene and N-(chloromethyl)phthalimide for 24-48 h. The product was poured on ice, filtered or extracted with chloroform (3 x 50 mL) and purified by column chromatography (SiO2, ethyl acetate/n-hexane) in order to obtain the title compoundsin high yields. 7.1.56 2-((2-(2-(Pentan-3-ylidene)hydrazono)-4-oxothiazolidin-3-yl)methyl)isoindoline-1,3-dione (4C) White powder, mp 155-156 C, 89% yield; 1H NMR (400 MHz, CDCl3): delta 0.87-0.91 (t, 3H, CH3), 1.09-1.12 (t, 3H, CH3), 2.28-2.34 (q, 2H, CH2), 2.38-2.44 (q, 2H, CH2), 3.83 (s, 2H, CH2, thiazolidinone), 5.73 (s, 2H, ArCH2), 7.74-7.76 (m, 2H, Ar), 7.86-7.88 (m, 2H, Ar).

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:
Article; De Monte, Celeste; Carradori, Simone; Bizzarri, Bruna; Bolasco, Adriana; Caprara, Federica; Mollica, Adriano; Rivanera, Daniela; Mari, Emanuela; Zicari, Alessandra; Akdemir, Atilla; Secci, Daniela; European Journal of Medicinal Chemistry; vol. 107; (2016); p. 82 – 96;,
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