Tag: M.W=200-300

Related Products of 20870-90-0, A common heterocyclic compound, 20870-90-0, name is 5-Bromo-1-methyl-2-oxoindoline, molecular formula is C9H8BrNO, 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 5-bromo-1-methyl-1,3-dihydro-2H-indol-2-one (1 g, 4 mmol) [Maybridge, cat10430564], 4,4,5,5,4?,4?,5?,5?-octamethyl-[2,2?]bi[[1,3,2]dioxaborolanyl] (1.7 g, 6.6 mmol), [1,1?-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complexed with dichloromethane (1:1) (200 mg, 0.2 mmol) and potassium acetate (1.3 g, 13 mmol) in 1,4-dioxane (40 mL) was purged with nitrogen and then stirred at 90 C. overnight. After cooling to room temperature, the reaction mixture was concentrated. The residue was purified by flash chromatography eluting with 0 to 25% EtOAc in hexanes to give the desired product. LC-MS calculated for C15H21BNO3 (M+H)+: m/z=274.1. found 274.1.

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; Incyte Corporation; Wu, Liangxing; Konkol, Leah C.; Lajkiewicz, Neil; Lu, Liang; Xu, Meizhong; Yao, Wenqing; Yu, Zhiyong; Zhang, Colin; He, Chunhong; (107 pag.)US2016/9712; (2016); A1;,
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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. 6941-75-9, name is 5-Bromoisoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C8H4BrNO2

Compound E-1 (110 mmmol) was refluxed in formamide for 4 hours to obtain compound E-2 (103 mmol, 94%).Compound E-2 (100 mmol) was reacted in 28% ammonia solution at room temperature for 24 hours to obtain compound E-3 (74 mmol, 74%).Compound E-3 (70 mmol) was dissolved in DMF,The mixture was allowed to react with thionyl chloride in an ice bath for 24 hours to obtain compound E-4 (53 mmol, 75%).

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 6941-75-9.

Reference:
Patent; NIPPON STEEL & SUMIKIN CHEMICAL COMPANY LIMITED; KYUSHU INSTITUTE OF TECHNOLOGY; HAYASE, SHUZI; PANDEY, SHYAM SUDHIR; YAMAGUCHI, YOSHIHIRO; OCHI, NORIAKI; FUJINO, KENICHI; OKAMOTO, ETSUYA; KOMAYA, YOHEI; (25 pag.)JP5906522; (2016); B2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 919103-45-0, name is 6-Iodoindolin-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 919103-45-0, Recommanded Product: 919103-45-0

0.88 g (7.23 mmol) 4-/V,/V-dimethylaminopyridine and 44.6 mL (101 .2 mmol) triethylamine are added successively to a suspension of 25.00 g (96.51 mmol) 6-iodo-1 ,3-dihydro-indol-2- one in 125.0 mL /V,/V-dimethylformamide. 27.81 g (197.8 mmol) benzoylchloride is added slowly at -10C to the reaction mixture and stirred for 2 h at -10C. After complete conversion (HPLC, Method A) 48.0 mL 10 M sodium hydroxide solution is added and stirred 1 h at room temperature. Then 350 mL water, 150 mL toluene and 80 mL cone, hydrochloric acid are successively added. The resulting precipitate is filtered, washed with water and toluene and dried at 50C in vacuo. [M+H]+: 364

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Iodoindolin-2-one, and friends who are interested can also refer to it.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ZAHN, Stephan Karl; BISTER, Bojan; SINI, Patrizia; WO2014/9319; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 104618-31-7, 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. 104618-31-7, name is 2-(4-Hydroxycyclohexyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

The title compound from Step A above (28 g, 114 mmol) was dissolved in dichloromethane (990 mL) and pyridinium chlorochromate (33.6 g, 157 mmol) was added in portions. The reaction mixture was stirred at room temperature for 8 h. Then another batch of pyridinium chlorochromate (10.4 g, 48.6 mmol) was added in portions and stirring at room temperature was continued for 18 h. The reaction mixture was filtered through a pad of Celite and the Celite pad was washed with dichlormethane (400 mL). The combined filtrate was concentrated under reduced pressure and the residue was purified by chromatography on silica using ethyl acetate/n-heptane (60/40) as a mobile phase to afford the title compound as a white solid (24.62 g, 88%)1H-NMR (400 MHz, CDCl3): delta=2.17-2.24 (m, 2H), 2.60-2.71 (m, 4H), 2.80-2.90 (m, 2H), 4.78 (tt, 1H), 7.84-7.88 (m, 2H), 7.97-8.02 (m, 2H)

The chemical industry reduces the impact on the environment during synthesis 2-(4-Hydroxycyclohexyl)isoindoline-1,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Patent; AC Immune, S.A.; US2011/280808; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 667463-64-1, name is 6-Bromo-1-methylindoline-2,3-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 667463-64-1, COA of Formula: C9H6BrNO2

I-3.1 (15.0 g, 63 mmol) and hydrazine hydrate (30 mL, 618 mmol) are heated to 125 C. for 72 h. To the cool reaction mixture DCM is added and extracted with water and 1 M HCl. The organic layer is dried over MgSO4 and concentrated. The crystallized residue is dissolved in DCM, methanol is added and the DCM is removed in vacuo. The crystallized product is filtered by sunction and washed with cold methanol. Yield 63%, m/z 226/228 [M+H]+, rt 1.16 min, LC-MS Method V001-003.

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, 6-Bromo-1-methylindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

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

Application of 868066-91-5, These common heterocyclic compound, 868066-91-5, name is 5-Bromo-2-methylisoindolin-1-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.

[00532] Intermediate Sic: 2-methyl-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yI)isoindolin-1-one[00533] A round bottomed flask containing bis(pinacolato)diboron (354mg, 1 .3gmmol) and KOAc (326mg, 3.32mmol) in 1 ,4-dioxane (6.5mL) was evacuated/backfilled with nitrogen. Pd(dppt)C12.CH2CI2 (54mg, 0.O7mmol) was added and the flask was evacuated/backfilled with nitrogen again. The reaction mixture was then stirred and heated at 85 C overnight. After this timethe mixture was cooled to room temperature, filtered through a plug of celite and the solid was washed with EtOAc. The filtrate was concentrated and the residue purified by column chromatography using an eluent of 0-100% EtOAc in heptane to give 2-methyl-5-(4,4,5,5- tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-one (324mg,1.lgmmol, 89% yield) as a brown solid.1H NMR (CDCI3, 400MHz) O/ppm: 7.92 (1H, dd, J= 7.6Hz, 0.4Hz), 7.90-7.89 (1H, m), 7.85 (1H, dd, J 7.6Hz, 0.4Hz), 4.39 (2H, 5), 3.23 (3H, 5), 1.38 (12H, 5).MS Method 3: RT: 3.61 mi m/z 274.1 [M+H]

The synthetic route of 868066-91-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; REDX PHARMA PLC; ARMER, Richard; BELFIELD, Andrew; BINGHAM, Matilda; JOHNSON, Alice; MARGATHE, Jean-Francois; AVERY, Craig; HUGHES, Shaun; MORRISON, Angus; (278 pag.)WO2016/51193; (2016); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference 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.

Adding a sodium hydroxide solution to the solution containing Compound I, And extracted with dichloromethane, Add Boc 2 O dropwise, react overnight, add water, separate dichloromethane, wash twice with saturated sodium chloride, dry over anhydrous sodium sulfate, concentrate, separate and purify by column chromatography, use 100-200 mesh silica gel column, wash Deionization using PE (petroleum ether): EA (ethyl acetate) = 40:1-20:1, to give an off-white solid 45g.

The synthetic route of 923590-95-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nanjing Xiaozhuang College; Shanghai Weifenqi Pharmaceutical Technology Co., Ltd.; Zhu Yuan; Wu Longzhong; Li Jianxiang; Yuan Yanfen; (11 pag.)CN109678787; (2019); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 954-81-4, These common heterocyclic compound, 954-81-4, name is N-(5-Bromopentyl)phthalimide, 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.

Step A: Preparation of 2-{(S)-1-[5-(1,3-Dioxo-1,3-dihydroisoindol-2-yl)pentyl]pyrrolidin-3-yl}-2,2-diphenylacetamide A 200-mL three-necked flask was charged with 2,2-diphenyl-2-(S)-pyrrolidin-3-ylacetamide, the intermediate from Example A (2.8 g, 10 mmol), N-(5-bromo-pentyl)phthalimide (3.55 g, 12 mmol), triethylamine (4.27 mL, 30 mmol) and ACN (100 mL). The reaction mixture was stirred at 55 C. for 8 hours and then concentrated under reduced pressure. IPAc was added to the residue and this mixture was washed with 0.5 N NaOH (2*100 mL), brine (1*100 mL), dried over magnesium sulfate, filtered and concentrated to give 5 g of the title intermediate (100% yield). MS m/z [M+H+] calc’d for C31H33N3O3 496.3; found 496.4.

Statistics shows that N-(5-Bromopentyl)phthalimide is playing an increasingly important role. we look forward to future research findings about 954-81-4.

Reference:
Patent; Theravance, Inc.; US2005/203161; (2005); A1;,
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 5332-26-3 as follows. Recommanded Product: 5332-26-3

Methyl 3-(1 ,3-dioxoisoindolin-2-yl)-2-(4-(triisopropylsilyloxy)phenyl) propanoate (E3) was prepared from E2 according to the below:To a solution of LiHMDS in THF cooled to -78C was added a cooled solution (approx – 78C) of methyl-2-(4-(triisopropylsilyloxy) phenyl)acetate (E2) in THF via syringe. The solution was stirred at -78C for 30 min. Bromo-methyl phthalimide was added directly to the anion, and the solution was immediately removed from the -78C bath and placed in an ice bath and stirred for 2 h. The reaction was then poured into NH4CI(sat) and extracted with EtOAc. The organics were dried (Na2SO4), filtered, and evaporated. Column chromatography 0-20% EtOAc/Hexanes gave pure methyl 3-(1 ,3-dioxoisoindolin-2-yl)-2-(4- (triisopropylsilyloxy)phenyl)propanoate (E3).

According to the analysis of related databases, 5332-26-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AERIE PHARMACEUTICALS, INC.; DELONG, Mitchell, A.; STURDIVANT, Jill, Marie; ROYALTY, Susan, M.; HEINTZELMAN, Geoffrey, Richard; YINGLING, Jeffrey, D.; KOPCZYNSKI, Casey; WO2010/127329; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 147149-84-6, A common heterocyclic compound, 147149-84-6, name is 4-Bromo-5-methylindoline-2,3-dione, molecular formula is C9H6BrNO2, 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.

Hydrogen peroxide (40 ml, 391.60 mmol) was added to a solution of 4-bromo-5-methyl-1H-indole-2,3-dione (20 g, 83.31 mmol) in 2M NaOH (400 ml) at rt. The resulting solution was stirred at rt for 2 h. Sodium sulfite (48 g) was then added and the mixture was stirred for another 0.5 h at rt. The reaction mixture was extracted with EtOAc (200 mL) and the aqueous layer pH adjusted to pH 4 with concentrated HCl. A precipitate was collected by filtration, washed with water (300 ml) and dried under vacuum to afford 6-amino-2-bromo-3-methylbenzoic acid (12.4 g, 65%) as a pale yellow solid; 1H NMR (400 MHz, MeOD, 30 C.) 2.29 (3H, s), 6.70 (1H, d), 7.07 (1H, d); m/z: ES+ [M+H]+=230.

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; ASTRAZENECA AB; Kettle, Jason Grant; Bagal, Sharanjeet; Robb, Graeme Richard; Smith, James Michael; Goldberg, Frederick Woolf; Cassar, Doyle Joseph; Feron, James Lyman; US2019/177338; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem