Tag: M.W=200-300

Synthetic Route of 2058-72-2, 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 2058-72-2 as follows.

General procedure: The mixture of corresponding 2-amino-4-arylimidazoles 1 (1.0 mmol), isatin 18 (1.0 mmol) andmalononitrile 12 (1.0 mmol) in 2 mL of 2-propanol was refluxed during 50-60 min. After cooling, the solid products 19 were filtered off and crystallized from iPrOH.

According to the analysis of related databases, 2058-72-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Lipson, Victoria V.; Pavlovska, Tetiana L.; Svetlichnaya, Nataliya V.; Poryvai, Anna A.; Gorobets, Nikolay Yu.; Van Der Eycken, Erik V.; Konovalova, Irina S.; Shiskina, Svetlana V.; Borisov, Alexander V.; Musatov, Vladimir I.; Mazepa, Alexander V.; Beilstein Journal of Organic Chemistry; vol. 15; (2019); p. 1032 – 1045;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 675109-26-9, name is 6-Bromoisoindolin-1-one, molecular formula is C8H6BrNO, 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. category: indolines-derivatives

A mixture of 6-bromoisoindolin-1-one (2.0 g, 9.44 mmol), bis(pinacolato)diboron (2.41 g, 9.7 mmol), KOAc (1.86 g, 18.66 mmol) and Pd(dppf)2C12 (0.39 g, 0.49 mmol) in dioxane (50 mE) was stirred at 1000 C. overnight under a nitrogen atmosphere. The mixture was poured into water and extracted with EtOAc (100 mLx3). The combined organic fractions were washed with brine, dried over sodium sulfate and concentrated under vacuum. The residue was purified by chromatography on silica gel (1/10 to 1/5 EtOAc in pet. ether) to give compound 13A (600 mg, 25% yield) as a white solid. ESI mlz 260.0 [M+1].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 675109-26-9, its application will become more common.

Reference:
Patent; Seal Rock Therapeutics, Inc.; BROWN, Samuel David; US2018/291002; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 21544-81-0, 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. 21544-81-0, name is 4,6-Dimethoxyindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

3,5-dimethoxy aniline (199g, 1.30mol) in diethyl ether (5.0 L) was added inthe flask 5L3 Cooled to 0 C. After 45 minutes the HCl gas (227g)introduced into the solution.at 10C 45 Minutes the mixture was filtered, (4L) and washed withisopropyl acetate, under high vacuum, dried at 45 C Night to give the hydrochloride as a white solid (242.3g, 98%). Under stirring the above hydrochloride (20g, 0The mixture.105mol) and oxalyl chloride (33 mL of) isequipped with a reflux condenser, 3-neck flask was heated 2 Hour (170 C externaltemperature), oxalyl chloride was distilled off from the reactionmixture. The flask was cooled to 0 C, was added methanol (40mL). The reactionmixture was heated at reflux for 45 minutes, filtered while hot, with A Alcohol(80mL) and washed to give a yellow-green solid4,6-dimethoxy isatin (17.2g, 79%). After 2 Hour to isatin (162g,0.78mol) was heated in aqueous NaOH solution(40%, 1.5L) in (externalTemperature 70 C) was slowly added to H 2 O 2(35%, 405mL). H 2 O 2 was added after each batch, the internal temperature of the reaction Degree(initially 64 C) increase (to a maximum temperature of 80 C). Afterthe addition was complete, then at 70 C will blister The reaction mixture wasstirred for an additional 2hours, the mixture was stirred overnight while cooling to roomtemperature. The mixtureIt was heated to 70 C. An additional H 2 O 2 (75mL), at 70 C and themixture was stirred for an additional 2 Hours until the reaction was complete.Cooled to 10 C (bath temperature), a solution of Na 2 S 2 O 3 solution (150mL, saturation). The mixture was washed with HCl (37%, 1.6L) was adjusted to pH8, with acetic acid(glacial acetic acid, 75mL) transfer To pH6, while not allowing thereaction mixture was warmed exceed 40 C. The reaction mixture was filtered,washed with water (4L) and washed to give the desired brownsolid amino acid (83.7g, 55%). The amino acid (82.7g, 0.42mol) (4.2L) was added in dry THF EDCl (89.2g, 0.48mol), HOBT(65g, 0.48mol) and NMM (51.3mL), and the mixturewas stirred at roomtemperature for 3 hours. Adding NH3 Aqueoussolution (83mL, 50%), and the mixture was stirred at room temperature for 16 hours.Was added water (1.25L), the The mixture (2 × 250mL) and extracted with DCM.Then the combined extracts were washed with water (2 × 500mL) washed Fandi.Concentrated, slurried with ethyl ether (550mL), filtered, and dried under highvacuum to afford a brown The solid4,6-dimethoxy-2-amino-benzamide (46.7g, 57%).2-Amino-4,6-dimethoxy – benzamide (1.06g, 5.4mmol), 3,5- dimethyl-4-hydroxy Benzaldehyde (0.810g,5.4mmol), K 2 CO 3 (0.747g, 5.4mmol) and I 2(1.645g, 6.5mmol) DMF (20mL) in mixing, at 80 C and the reaction mixture was heated for 12 hours. It was cooledto Room temperature, poured onto crushed ice. The solid was collected, whichwas purified by column chromatography to give a white solid State of 2- (4-hydroxy-3,5-dimethylphenyl)-5,7-dimethoxy-quinazolin -4 (3H) – one (0.9g, 51%). Selected data:MP291-293 C.

The synthetic route of 4,6-Dimethoxyindoline-2,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RESVERLOGIX CORP; HANSEN, H; (62 pag.)CN103319408; (2016); B;,
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 3339-73-9 as follows. Quality Control of 3-(1,3-Dioxoisoindolin-2-yl)propanoic acid

A solution of 28 (2.000 g, 9.12 mmol), DPPA (1 .966 mL, 9.12 mmol, 1 eq) and TEA (2.543 ml, 2 eq, 1 8.25 mmol) in dry toluene (60 mL) was stirred at rt, under a nitrogen atmosphere. After disappearance of starting materials by TLC (approximately 1 hour), the mixture was refluxed to promote conversion to the isocyanate. After evolution of nitrogen gas had ceased, the reaction mixture was split into half (by volume). 2-aminophenol (747 mg, 1.5 eq, 6.84 mmol) was added to one half of the isocyanate solution and stirred under reflux for 16 hours. On cooling to rt a yellow precipitate formed, which was collected by filtration (suction) and washed with EtOAc. On drying, 867 mg of pale yellow solid was obtained requiring no further purification.

According to the analysis of related databases, 3339-73-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THE UNIVERSITY OF NOTTINGHAM; MISTRY, Shailesh; DARAS, Etienne; FROMONT, Christophe; JADHAV, Gopal; FISCHER, Peter Martin; KELLAM, Barrie; HILL, Stephen John; BAKER, Jillian Glenda; WO2012/4549; (2012); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 20780-72-7, name is 4-Bromoisatin, 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 20780-72-7, category: indolines-derivatives

General procedure: To a solution of isatin derivative (0.68mmol, 1.0eq) in DMF (4mL) was added K2CO3 (0.68mmol, 1.0eq) at room temperature, the mixture was stirred for about 30min, and then the propargyl bromide (0.75mmol, 1.1eq) was added dropwise. The mixture was stirred for 6?10hat room temperature depending on the isatin derivative used. Upon completion, EtOAc and H2O were added. The aqueous layer was extracted with EtOAc; the combined organic layers were washed with H2O for several times to remove the DMF, and then washed with brine, dried over MgSO4 and evaporated to give the products. Yellow solid, yield: 89percent, m. p.: 153.1?154.9°C, Rf=0.26 (petroleum ether/ethyl acetate=2/1). 1H NMR (400MHz, CDCl3) delta 7.49 (t, J=8.0Hz, 1H), 7.33 (d, J=8.1Hz, 1H), 7.11 (d, J=7.9Hz, 1H), 4.57 (d, J=2.5Hz, 2H), 2.34 (t, J=2.5Hz, 1H).13C NMR (100MHz, CDCl3) delta 179.90, 156.21, 151.10, 138.42, 128.93, 121.74, 116.52, 109.86, 75.36, 73.67, 30.94, 29.53

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, 4-Bromoisatin, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Yu, Bin; Qi, Ping-Ping; Shi, Xiao-Jing; Huang, Ruilei; Guo, Hao; Zheng, Yi-Chao; Yu, De-Quan; Liu, Hong-Min; European Journal of Medicinal Chemistry; vol. 117; (2016); p. 241 – 255;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 2058-72-2, These common heterocyclic compound, 2058-72-2, name is 5-Bromo-1-methylindoline-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.

General procedure: A mixture of aminorhodanine (1 mmol), isatin (1 mmol) and 5 muL of acetic acid in 2mL of distilled ethanol was placed in a cylindrical quartz reactor (Phi = 4 cm). The reactor was introducedinto a monomode microwave (Anton Paar) apparatus, for 5 min at100 C and 50 Watts. The crude reaction mixture was allowed tocool down at room temperature and ethanol (10 mL) or mixture of H2O/EtOH (10 mL) was directly added in the cylindrical quartzreactor. The resulting precipitated product was filtered off and waspurified by recrystallization from ethanol if necessary.

The synthetic route of 2058-72-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Khaldoun, Khadidja; Safer, Abdelmounaim; Boukabcha, Nourdine; Dege, Necmi; Ruchaud, Sandrine; Souab, Mohamed; Bach, Stephane; Chouaih, Abdelkader; Saidi-Besbes, Salima; Journal of Molecular Structure; vol. 1192; (2019); p. 82 – 90;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 883-44-3, A common heterocyclic compound, 883-44-3, name is 2-(3-Hydroxypropyl)isoindoline-1,3-dione, molecular formula is C11H11NO3, 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.

N1-Boc-N4-Nbs-N4-(3-propyl-1-phthalimide)-trans-1,4-diaminocyclohexaneA solution of 310 mg (0.78 mmol) of N4-Boc-N1-Nbstrans-1,4-diaminocyclohexane was dissolved in 20 mL of 1:3 CH2Cl2/benzene together with 254 mg (0.97 mmol) of Ph3P and 127 mg (0.62 mmol) of N-(3-hydroxypropyl)phthalimide. The resulting solution was stirred at 25 C. under argon. To this solution was added 191 L (0.97 mmol) of a 40% solution of DIAD in toluene dropwise. After addition was complete, stirring was continued for an additional 18 hours. The solution was evaporated to dryness and the crude oil purified on silica gel eluting first with 8:2 Hexane/EtOAc then with 1:1 Hexane/EtOAc to give a total of 322 mg (89%) of product as a clear oil (Rf 0.35 (1:1 Hexane/EtOAc

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; Burns, Mark R.; McVean, Maralee; Kennedy, Kevin J.; Yeung, Arthur; Devens, Bruce H.; US2004/235960; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 923590-95-8,Some common heterocyclic compound, 923590-95-8, name is 4-Bromoisoindoline hydrochloride, molecular formula is C8H9BrClN, 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.

A solution of 4-bromoisoindoline hydrochloride (8.00 g, 34.33 mmol) in dichloromethane (20 mL) and triethylamine (14.3 mL, 103.0 mmol) was cooled to 0 C, and then di-tert-butyl dicarbonate (15.0 g, 68.73 mmol) was added. The mixture stirred overnight at room temperature and was then quenched by the addition of 50 mL of water. The resulting solution was extracted with 3×50 mL of dichloromethane, washed with 1×50 mL of brine, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was purified via column chromatography on silica gel (eluting with ethyl acetate/petroleum ether (1 :5)) to afford tert-butyl 4-bromoisoindoline-2-carboxylate (9 g, 75%) as a white solid. MS: (ESI, m/z): 242 [M-t-Bu+H]+

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

Reference:
Patent; FORMA THERAPEUTICS, INC.; ZHENG, Xiaozhang; MARTIN, Matthew W.; NG, Pui Yee; THOMASON, Jennifer R.; HAN, Bingsong; RUDNITSKAYA, Aleksandra; LANCIA, JR., David R.; (180 pag.)WO2019/204550; (2019); 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. 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., SDS of cas: 5332-26-3

A solution of intermediate ACi (2.03 g) in THF (19 mL) was added dropwise at -78C to a solution of LiHMDS (IM in THF; 10.5 mL) in THF (10 mL). The solution was further stirred at -78C stirred for 1 h and treated dropwise with a solution of Lambda/-(bromomethyl)phthalimide (2.6 g) in THF (19 mL). The reaction mixture was further stirred at -78C for 1 h and at rt overnight. The solution was quenched with IN HCl (30 mL) and extracted with EA. The org. layer was washed with water and brine, dried over MgSO4, concentrated under reduced pressure and purified by CC (Hept/EA 1 :1), affording, after crystallization from EA, a beige solid (2.28 g; 66% yield). MS (ESI, m/z): 392.3 [M+H+].

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; ACTELION PHARMACEUTICALS LTD; HUBSCHWERLEN, Christian; RITZ, Daniel; RUEEDI, Georg; SURIVET, Jean-Philippe; ZUMBRUNN ACKLIN, Cornelia; WO2010/41194; (2010); 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. 897957-06-1, name is 6-Bromo-1-methylindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 6-Bromo-1-methylindolin-2-one

To I-3.2 (32.0 g, 142 mmol) in anhydrous dioxane (400 mL) is added R8 (54.4 g, 241 mmol) and potassium acetate (41.6 g, 424 mmol). The mixture is purged with Argon, [1,1?-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) as a complex with dichloromethane (11.2 g, 14 mmol) is added and the mixture is heated to 90 C. for 2 h. The reaction mixture is diluted with ethyl acetate and water, the organic layer is washed with water, dried over MgSO4 and concentrated. The residue is purified via flash chromatography (cyclohexane/EA=70:30). Yield 72%, m/z 274 [M+H]+, rt 0.67 min, LC-MS Method V011_S01.

According to the analysis of related databases, 897957-06-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GRAUERT, Matthias; ANDERSKEWITZ, Ralf; GRUNDL, Marc; OOST, Thorsten; PAUTSCH, Alexander; PETERS, Stefan; US2014/275155; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem