Author: Jessica.F

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., name: 1-Acetylindolin-3-one

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.

According to the analysis of related databases, 16800-68-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Mahajan, Suruchi; Chauhan, Pankaj; Loh, Charles C. J.; Uzungelis, Server; Raabe, Gerhard; Enders, Dieter; Synthesis; vol. 47; 7; (2015); p. 1024 – 1031;,
Indoline – Wikipedia,
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Related Products of 496-12-8, 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 496-12-8 as follows.

Sodium triacetoxyborohydride (0.47 g, 2.22 mmol) was added to a solution of isoindoline (0.22 g, 1.85 mmol), tert-butyl 4-formyl-1-piperidinecarboxylate (0.40 g, 1.88mmol) and acetic acid (0.033 mL, 0.58 mmol) in dichloromethane (10 mL) and the resulting mixture was stirred overnight at room temperature. The reaction mixture was partitioned between excess of diethyl ether and water. The organic phase was separated, washed with diluted aqueous sodium hydroxide solution, dried over sodium sulfate and the solvent was evaporated to give the title compound (0.61 g, 83%)LRMS (mlz): 317 (M+1)+.

According to the analysis of related databases, 496-12-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ALMIRALL, S.A.; BACH TANA, Jordi; PEREZ CRESPO, Daniel; LLERA SOLDEVILA, Oriol; ESTEVE TRIAS, Cristina; TABOADA MARTINEZ, Lorena; WO2015/86693; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 201940-08-1, 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. 201940-08-1, name is tert-Butyl 5-bromoisoindoline-2-carboxylate belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Synthesis of AM374-A. To a degassed mixture of tert-butyl 5-bromoisoindoline-2- carboxylate (1 g, 3.35 mmol), 1-methylpiperazine (403 mg, 4.03 mmol), Xanthphos (97 mg, 0.17 mmol) and NaOBut (482 mg, 5.03 mmol) in toluene (10 mL) was added Pd2(dba)3 (153 mg, 0.17 mmol) under N2 and the mixture was stirred at 100C overnight. The reaction mixture was concentrated in vacuo. The residue was dissolved in ethyl acetate (50 mL) and washed with brine (30 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography on silica gel (MeOH:CHCl3=99:1~95:5) to give AM374-A (800 mg, 75%) as a white solid

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, tert-Butyl 5-bromoisoindoline-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; RODIN THERAPEUTICS, INC; JEFSON, Martin, R.; LOWE, John, A., III; DEY, Fabian; BERGMANN, Andreas; SCHOOP, Andreas; FULLER, Nathan, Oliver; (165 pag.)WO2017/7756; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 340702-10-5, A common heterocyclic compound, 340702-10-5, name is 6-Fluoroisoindolin-1-one, molecular formula is C8H6FNO, 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.

[0143] Step a: To a stirred solution of 6-fluoroisoindolin-l-one (10 g, 66.2 mmol) in anhydrous dichloromethane (100 mL) were added triethylamine (16.72, 165.5 mmol, 21.8 mL), (Boc)20 (17.3 g, 79.4 mmol) and catalytic DMAP (100 mg) at room temperature. The reaction mixture was stirred at room temperature for 16 h. After completion, the reaction mixture was diluted with CH2C12, washed with H20, and then saturated aqueous NaHCC>3. The organic layer was dried over Na2S04i filtered, and concentrated in vacuo. The crude compound was purified by silica gel chromatography (0-30% ethyl acetate in hexanes) to give the product. MS: (ES) m/z calculated for C13H14FNO3 [M + H]+ 252.3, found 252.3

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:
Patent; CHEMOCENTRYX, INC.; CHEN, Xi; DRAGOLI, Dean, R.; FAN, Junfa; KALISIAK, Jaroslaw; LELETI, Manmohan, Reddy; MALATHONG, Viengkham; MCMAHON, Jeffrey; TANKAKA, Hiroko; YANG, Ju; YU, Chao; ZHANG, Penglie; MALI, Venkat; (104 pag.)WO2017/87610; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 15362-40-0, A common heterocyclic compound, 15362-40-0, name is 1-(2,6-Dichlorophenyl)-2-indolinone, molecular formula is C14H9Cl2NO, 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.

Example 4Step a) of preparation of Potassium diclofenacIn a four-necked glass flask the following ingredients were charged:1 -(2,6-dichlorophenyl)-2-indolinone g 100 (moles: 0.359) – Water cc 435- Sodium hydrosulfite g 4- Potassium hydroxide 90 % g 33.6 (moles: 0.539)The mixture was refluxed for 8h 30 min, then cooled to 35 – 37 C. The precipitate was filtered on buchner funnel, then washed with a 1 % NaCI solution in water (cc 70) preheated to 35 C. Wet 180,2 grams of potassium diclofenac were obtained corresponding to dry 1 12,1 grams (Theor. g 120.17).

The synthetic route of 15362-40-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; COSMA S.P.A.; IBSA INSTITUT BIOCHIMIQUE S.A.; AVOGADRI, Alvaro; LUSSANA, Massimiliano; PIZZATTI, Enrica; BARETTI, Sergio; WO2010/69397; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 17564-64-6, 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. 17564-64-6 name is 2-(Chloromethyl)isoindoline-1,3-dione, 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.

NONOate salt NS-01 (0.270 g, 1.58 mmol) suspended in acetonitrile (3.0 mL) was treated with a solution of N-(chloromethyl)phthalimide (0.280 g, 1.43 mmol) in acetonitrile (3.0 mL) and then sodium iodide (0.215 g, 1.43 mmol) was added. The resulting mixture was stirred at 25 C overnight. N,N-dimethylformamide (1.0 mL) was added to the reaction mixture which was then heated to 60 C for 1 hour. The acetonitrile was removed under reduced pressure. The residue was suspended in ethyl acetate and then washed with a 0.2 N solution of sodium thiosulfate. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated. The residue was subjected to prep-chromatography using ethyl acetate in hexane to provide a tan oily solid (14 mg, 3.0% yield). 1H NMR (400 MHz, CDCI3) delta 7.92-7.87 (m, 2H), 7.78-7.73 (m, 2H), 5.67 (s, 2H), 2.97 (s, 1H), 2.19 (s, 2H), 1.59 (s, 6H). LC tr=2.65 minutes (C-18 column, 5 to 95% acetonitrile/water over 6 minutes at 1.7 mL/min with detection 254 nm, at 23 C). ES(pos)MS m/z 331 (M+Na calcd for C13H16N4O5 requires 331).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(Chloromethyl)isoindoline-1,3-dione, and friends who are interested can also refer to it.

Reference:
Patent; SARMONT LLC; MARTINEZ, Eduardo J.; TALLEY, John J.; JEROME, Kevin D.; BOEHM, Terri L.; WO2015/108835; (2015); 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. 13220-46-7, name is 4-Methylindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 13220-46-7

5-Chloro-4-methyl-2-oxindole A suspension of 3.0 g of 4-methyl-2-oxindole was stirred in 50 ML of acetonitrile at room temperature while 3.3 g of N-chlorosuccinimide was added in portions.. trifluoroacetic acid (1 ML) was then added.. The suspension was stirred at room temperature for 3 days during which time solid was always present.. The white solid was collected by vacuum filtration, washed with a small amount of cold acetone and dried overnight in a vacuum oven at 40 C. to give 2.5 g (68%) of 5-chloro-4-methyl-2-oxindole.

According to the analysis of related databases, 13220-46-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sugen, Inc.; US6350754; (2002); B2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-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. Application In Synthesis of 2-(Bromomethyl)isoindoline-1,3-dione

To a suspension of NaH (2.2 g, 54 mmole) in THF (200 ml_) was added diethyl 2-(phenylmethyl)butanedioate (12.5 g, 49.9 mmole). After 30 min at RT, bromomethyl phthalimide was added to the reaction mixture and the contents were stirred for 14 h at RT. The reaction was quenched with H2O (15 mL), diluted with Et2O (300 mL) and layers separated. The organic layer was concentrated under vacuum and the resulting residue recrystallized from EtOH (0) to give the title compound (13 g, 64%) as a white solid: LCMS (ES) m/z 410 (M+H)+.

The synthetic route of 2-(Bromomethyl)isoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2007/76423; (2007); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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 6341-92-0 as follows. Recommanded Product: 6-Chloroisatin

General procedure: In a 25 mL round bottom flask, isatins 1 (1 mmol), 3-phenylisoxazol-5(4H)-one 2 (1 mmol) or 3-ethylisoxazol-5(4H)-one 7 (1 mmol), pyrazol-5-amine 3 (1 mmol) or 6-aminopyrimidine-2,4-(1H,3H)-dione 5 (1 mmol), and Amberlyst-15 (100 mg) were stirred in CH3OH (5.0 mL) at 80 C. When the reaction was completed (detected by TLC), the spherical catalyst was separated by a sieve at once under hot condition. Then, the reaction mixture was cooled to room temperature, and solid precipitation occurred. After filtration, the crude product was recrystallized from EtOH and DMF to give pure compound.

According to the analysis of related databases, 6341-92-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Niu, Qingqing; Xi, Junhua; Li, Lei; Li, Li; Pan, Chengli; Lan, Meijun; Rong, Liangce; Tetrahedron Letters; vol. 60; 43; (2019);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 172078-33-0, These common heterocyclic compound, 172078-33-0, name is Indolin-5-ol, 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.

Compound 1E (100 mg, 423 mmol), compound 24A (63 mg, 465 mmol) and cesium carbonate (303 mg, 930mmol) were added to NMP (1 mL). The reaction solution was heated to 120 C and stirred for 2 hours, and then thereaction was quenched with water, and extracted with ethyl acetate (3 x 10 ml). The organic layer was washed withsaturated NaCl solution, dried over anhydrous sodium sulfate, filtered and evaporated to dryness. The residue waschromatographed on a silica gel plate (dichloromethane/methanol = 10: 1, Rf = 0.2) and purified to give compound 24B(yellow solid, 80 mg, 57%).LCMS (ESI) m/z: 336.1(M+1)+

Statistics shows that Indolin-5-ol is playing an increasingly important role. we look forward to future research findings about 172078-33-0.

Reference:
Patent; GUANGDONG ZHONGSHENG PHARMACEUTICAL CO., LTD; LONG, Chaofeng; CHEN, Zhengxia; CHEN, Xiaoxin; ZHANG, Yang; LIU, Zhuowei; LI, Peng; CHEN, Shuhui; LIANG, Guibai; XIE, Cheng; LI, Zhengwei; FU, Zhifei; HU, Guoping; LI, Jian; (276 pag.)EP3293177; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem