Month: August 2021

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

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. 3416-57-7, name is 2-(2-Oxopropyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Formula: C11H9NO3

5.5. Examples 5-13; Similar to Examples 3 and 4,5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-ol was prepared using the following solvent/base combinations for the preparation of the 2-amino-4-methyl-1H-pyrrole-3-carboxamide intermediate:

According to the analysis of related databases, 3416-57-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bednarz, Mark S.; Kanamarlapudi, Ramanaiah C.; Wu, Wenxue; US2008/97098; (2008); 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. 20870-90-0, name is 5-Bromo-1-methyl-2-oxoindoline, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 20870-90-0

To a solution of 5-bromo-1-methyl-1 ,3-diotahydro-indol-2-one (CASNo. 20870-90-0, 4.07 g, 18.00 mmol). in DMSO (50 mL) was added biotas(pinaco.ato)diboron (5 03 g, 19.80 mmol), and potassium acetate (5.30 g, 54 0 mmol) Next, [1 , 1 ‘-biotas(diphenylphosphiotano)- ferrocene]-d(chloropalladiotaum(ll) complexed with dichloromethane (CASNo. 72287-26-4, 0 417 g, 0 540 mmol) was added The reaction mixture was degassed by bubbling nitrogen through the solution for 3 minutes The reaction was then heated at 80 C for 18 hr The reaction was then poured into ice-water and extracted three times with diethyl ether, The organic extracts were combined, washed with brine, dned over anhydrous sodium sulfate, filtered and concentrated The resulting residue was purified by silica gel flash chromatography (ethyl acetate-heptane, O to 70%) to afford 1-methyl-5-(4,4,5,5- tetramethyl-(1 ,3,2Jdioxaboro.an-2-yl)-1 ,3-diotahydro-indol-2-one, 1H NMR (400 MHz1 CDCI3) delta ppm 1 35 (s, 12 H), 3.23 (s, 3 H), 3.51 (s, 2 H), 6 83 (d, J=7,6 Hz, 1 H), 7.69 (S1 1 H)1 7,77 (d, J= 7 8 Hz, 1 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 20870-90-0.

Reference:
Patent; NOVARTIS AG; ADAMS, Christopher Michael; CHAMOIN, Sylvie; HU, Qi-Ying; ZHANG, Chun; WO2010/130794; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 201940-08-1, 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. 201940-08-1, name is tert-Butyl 5-bromoisoindoline-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

0.69 ml of n-Butyl lithium (2.5M solution in hexane) was added dropwise to a stirred solution of 5- bromo-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester (429 mg; 1.44 mmol) in anhydrous THF (10 ml) at -78C under an atmosphere of nitrogen. The reaction was stirred for 50 minutes then 1-methyl-4-piperidone (212 mul; 1.2 equiv.) was added and stirred at -78C for a further 60 minutes then warmed to room temperature. The reaction was quenched with saturated ammonium chloride solution then extracted with EtOAc. The EtOAc layer was washed with saturated NaHCO3, brine, dried (MgSO4) and evaporated. Purification by flash column chromatography on SiO2, gradient elution from 0% to 10% 2M methanolic ammonia / DCM gave 111 mg of 5-(4-hydroxy-1-methyl- piperidin-4-yl)-1 ,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester as a colourless oil.

The chemical industry reduces the impact on the environment during synthesis tert-Butyl 5-bromoisoindoline-2-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; WO2008/44045; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 611-09-6, name is 5-Nitroindoline-2,3-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. Recommanded Product: 5-Nitroindoline-2,3-dione

General procedure: A mixture of an isatin (1mmol), molononitrile (1mmol), CH activatedacid (1mmol), and [C4(DABCO)2]·2OH(2mol%) inwater (3mL)was stirred at 80 C. The reaction progress was monitored by TLC [eluent:n-hexane:EtOAc (9:2)] (It is important to that by beginning of thereaction the products were precipitated in the reaction medium).After completion of the reaction, the mixture was cooled to room temperature and the solid product was filtered, washed with cold distilledwater (2 mL) to obtain essentially pure products. The solid productswere recrystallized from ethanol if necessary.

The synthetic route of 5-Nitroindoline-2,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Goli-Jolodar, Omid; Shirini, Farhad; Seddighi, Mohadeseh; Journal of Molecular Liquids; vol. 224; (2016); p. 1092 – 1101;,
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. 50727-04-3, name is 5-Methoxyisoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Computed Properties of C9H7NO3

EXAMPLE 4 4-(1,3-Dioxo-5-methoxy-1,3-dihydroisoindol-2-yl)-2-{1-[2-(4-methoxy-phenyl)-1-(methylcarbamoyl)ethylcarbamoyl]cyclohexylmethyl}butyric acid 4-(1,3-Dioxo-5-methoxy-1,3-dihydroisoindol-2-yl)-2-{1-[2-(4-methoxy-phenyl)-1-(methylcarbamoyl)ethylcarbamoyl]cyclohexylmethyl}butyric acid (mixture of diastereomers) starting with the reaction of 4-hydroxy-2-{1-[2-(4-methoxyphenyl)-1-(methylcarbamoyl)ethylcarbamoyl]cyclohexylmethyl}butyric acid tert-butyl ester with 1,3-dioxo-5-methoxy-1,3dihydroisoindole.

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; Pfizer Inc.; US5854275; (1998); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 5332-26-3,Some common heterocyclic compound, 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, molecular formula is C9H6BrNO2, 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: Appropriate bromide (1.5 mmol) was dissolved in 15 mL of DMF (dried) and sodium azide (1.6 mmol, 104 mg) was added. The mixture was stirred vigorously at room temperature. After 12 h the reaction was quenched by adding 15 mL of distilled water (slightly exothermic reaction). The cooled reaction mixture (room temperature) was extracted twice with 30 mL of diethyl ether and washed with water (once with 20 mL). The separated organic layer was dried over anhydrous sodium sulphate and evaporated to dryness. The product obtained as white solid was washed with 30mL of distilled water.

The synthetic route of 5332-26-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Pyta, Krystian; Klich, Katarzyna; Domagalska, Joanna; Przybylski, Piotr; European Journal of Medicinal Chemistry; vol. 84; (2014); p. 651 – 676;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 169037-23-4, 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 169037-23-4 as follows.

General procedure: A mixture of indoline-2,3-dione 1 (1mmol), l-tryptophan (2a) or l-histidine 2b (1mmol) and (E)-(2-nitrovinyl)benzene 3 (1.1mmol) was heated while stirred in [bmim]Br as the reaction medium (3mL) for 1hat 100C. After completion of the reaction (TLC), EtOAc (5mL) was added and the reaction mixture was stirred for 10min. This treatment was repeated and the combined ethyl acetate layers were removed in vacuo. The crude product was purified by recrystallization of the residue from EtOH (compounds 4) or by column chromatography (compounds 5). After extraction of the product, the ionic liquid was dried under vacuum at 80C for 2h to eliminate any water and could be reused for subsequent runs of the reaction.

According to the analysis of related databases, 169037-23-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Arumugam, Natarajan; Almansour, Abdulrahman I.; Kumar, Raju Suresh; Periasamy, Vaiyapuri Subbarayan; Athinarayanan, Jegan; Alshatwi, Ali A.; Govindasami, Periyasami; Altaf, Mohammad; Menendez, J. Carlos; Tetrahedron; vol. 74; 38; (2018); p. 5358 – 5366;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem