Month: May 2021

Adding a certain compound to certain chemical reactions, such as: 6941-75-9, name is 5-Bromoisoindoline-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 6941-75-9, Computed Properties of C8H4BrNO2

EXAMPLE 5; Step 5A: Bromophthalimide 5a (13.0 g, 57.8 mmol) was added in six portions over 30 minutes to a stirred suspension of zinc powder (4.50 g, 69.2 mmol) and copper (II) sulfate pentahydrate (0.060 g, 0.25 mmol) in aqueous sodium hydroxide (2 M, 71 mL) at 0 C (ice-bath. ) The mixture was stirred at 0 C for an additional 30 minutes, and at room temperature for 2.5 h to complete the reaction. After filtering, the reaction solution was neutralized to pH 7 with 20% hydrochloric acid, diluted with 100 mL of ethanol, and then extracted with ethyl acetate. The extract was washed with brine, dried with MgS04 and concentrated in vacuo to afford 12.5 g (95%) of 5b as a yellow solid, LC-MS 210 (MH+-H20.)

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:
Patent; NEUROCRINE BIOSCIENCES, INC.; WO2005/103039; (2005); 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. 201940-08-1, name is tert-Butyl 5-bromoisoindoline-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 201940-08-1

Tris(dibenzylideneacetone)dipalladium(0) (228 mg, 0.25 mmol), 2-(di-tert-butylphosphino)biphenyl (149 mg, 0.50 mmol) and sodium tert-butoxide (1.34 g, 13.9 mmol) were added into a solution of 5-bromo-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester (2.97 g, 10 mmol) in toluene (15 mL). The reaction mixture was purged with argon for 5 minutes and then N-methylpiperazine (1.33 mL, 12 mmol) was added and the mixture and stirred at 80 C. for 4 hours. After the completion of the reaction (monitored by TLC) the solvent was removed under vacuum, water (3 mL) was added, and the reaction mixture was extracted with dichloromethane (3*30 mL). The combined organic extracts were dried over Na2SO4. The solvents were removed under vacuum and the residue was purified on silica gel (Biotage; eluting solvents 5% MeOH in dichloromethane) to afford tert-butyl 5-(4-methylpiperazin-1-yl)isoindoline-2-carboxylate as brown solid (1.75 g, 55% yield); 1H NMR (400 MHz, MeOH-d4) delta ppm 7.16-7.12 (m, 1H), 6.92-6.88 (m, 2H), 4.59-4.53 (m, 4H), 3.19-3.17 (m, 4H), 2.63-2.60 (m, 4H), 2.34 (s, 3H), 1.51 (9H, s).

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 201940-08-1.

Reference:
Patent; Malamas, Michael; Makriyannis, Alexandros; Lamani, Manjunath; Farah, Shrouq I.; US2019/152917; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 496-12-8, These common heterocyclic compound, 496-12-8, name is Isoindoline, 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.

3-lodobenzoic acid (248 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 was stirred at room temperature overnight. The reaction mixture was concentrated, diluted with EtOAc, and washed with water, 1N 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 304 mg (87%) of the product as a tan solid. MS (+ESI): m/z 349.9 [M+H]+.

Statistics shows that Isoindoline is playing an increasingly important role. we look forward to future research findings about 496-12-8.

Reference:
Patent; WYETH LLC; LI, David, Zenan; O’NEIL, Steven, Victor; SPRINGER, Dane, Mark; ZEGARELLI, Benjamin, Miller; WO2010/124047; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 18711-13-2,Some common heterocyclic compound, 18711-13-2, name is 4,7-Dichloroindoline-2,3-dione, molecular formula is C8H3Cl2NO2, 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 NiO-SiO2 catalyst (6.5 mol%) was added to a mixture of isatin (1 mmol), malononitrile (1 mmol), and 3-methyl-1-phenyl-1H-pyrazol-5-amine (1 mmol) in EtOH, and the reaction flask was placed in an oil bath and refluxed for the appropriate time. The progress of reaction was monitored by TLC. After the completion of the reaction, the heterogeneous catalyst was recovered from the reaction mixture by filtration. The filtrate was evaporated to afford the crude solid product which was later purified by column chromatography. The solid catalyst was washed with hot EtOH and then dried in oven to reuse.

The synthetic route of 18711-13-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yagnam, Swetha; Akondi, Adinarayana Murthy; Trivedi, Rajiv; Rathod, Balaji; Prakasham, Reddy Shetty; Sridhar; Synthetic Communications; vol. 48; 3; (2018); p. 255 – 266;,
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. 32692-19-6, name is 5-Nitroindoline, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 32692-19-6

5-Nitro-1-(2-(pyrrolidin-1-yl)ethyl)indoline (3) A solution of compound 2 (500 mg, 3.05 mmol) in DMF (10 mL) was treated with NaH (390 mg, 9.75 mmol, 60% wt in mineral oil) at 0 C. resulting in a bright orange suspension. The mixture stirred for 10 minutes, then 2-chloroethyl-pyrrolidine hydrochloride (566 mg, 3.33 mmol) was added and the reaction turned into a bright red suspension. The reaction was heated to 90 C. for 1 hour. After 1 hour, the reaction was allowed to cool to room temperature. Then it was diluted with water (20 mL), transferred to a separatory funnel and extracted with ethyl acetate (2*15 mL). The combined the organic layers were washed with brine (3*5 mL), dried (Na2SO4), filtered and concentrated. The residue was subjected to flash chromatography on silica gel using: 2.5% 2M NH3 in methanol: 97.5% CH2Cl2 to give a brown solid (400 mg, 50%). 1H-NMR (DMSO-d6) delta 7.96 (dd, J=2.4, 9.0 Hz, 1H), 7.80 (d, J=2.1 Hz, 1H), 6.47 (d, J=9.0 Hz, 1H), 3.73 (t, J=9.0 Hz, 2H), 3.41 (t, J=6.9 Hz, 2H), 3.04 (t, J=8.1 Hz, 2H), 2.62 (t, J=6.9 Hz, 2H), 2.58-2.48 (m, 4H), 1.70-1.64 (m, 4H).

According to the analysis of related databases, 32692-19-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MADDAFORD, Shawn; RAMNAUTH, Jailall; RAKHIT, Suman; PATMAN, Joanne; ANNEDI, Subhash C.; ANDREWS, John; DOVE, Peter; SILVERMAN, Sarah; Renton, Paul; US2008/234237; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 89-40-7, The chemical industry reduces the impact on the environment during synthesis 89-40-7, name is 5-Nitroisoindoline-1,3-dione, I believe this compound will play a more active role in future production and life.

General procedure: The substrate (0.5 mmol), NiPd/MIL-101 catalyst (0.023g, Pd 0.2 mol%), and ethyl acetate (4 mL) were added to a Schlenk tube, and the mixture was vigorously stirred with an affixed hydrogenation balloon at room temperature. Following the reaction, the solid catalyst was removed from the solution by filtration and washed with ethyl acetate. The product yields were determined by gas chromatography-mass spectrometry (GC/MS, Shimadzu GCMS- QP5050A) with a 0.25 mm ¡Á 30 mDB-WAX capillary column. Parameters were as follows: initialoven temperature, 100 C, 1 min; ramp, 20 C/min; final temperature, 280 C; final time, 5 min.

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, 5-Nitroisoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Jian, Siping; Li, Yingwei; Cuihua Xuebao/Chinese Journal of Catalysis; vol. 37; 1; (2016); p. 91 – 97;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 14192-26-8, 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. 14192-26-8, name is Methyl 2-oxoindoline-6-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

The intermediate from Step D was esterified by heating in acidic methanol overnight. The resulting solution was concentrated under vacuum and the residue was dissolved in hot ethanol (75 mL). Methanol (20 mL) was added to redissolve some material that precipitated as the solution cooled. Sodium nitrite (1.50 g) was added, followed by concentrated hydrochloric acid (5 mL). The reaction was stirred for 2 h, and a further concentrated hydrochloric acid (2 mL) was added. The reaction was stirred overnight. Volatiles were removed under reduced pressure, water added, and the resulting yellow orange product was isolated by filtration and dried under vacuum to give the intermediate (2.1 g) as a yellow orange solid. [MH]+=221.

The chemical industry reduces the impact on the environment during synthesis Methyl 2-oxoindoline-6-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Alantos Pharmaceuticals, Inc.,; US2006/173183; (2006); 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 7699-18-5 as follows. COA of Formula: C9H9NO2

General procedure: To the 3-subtitutedphenyl-1H-pyrazole-5-carbaldehydes 11(a-d) prepared in the above step was added corresponding substituted oxindoles and catalytic amount of piperdine (1.0ml) in ethanol. Heated the reaction mixture to reflux for 4h at 85C. The solid compounds obtained in the reaction vessel were filtered and washed with ethanol for 4-5 times. After complete air drying the final compounds (Z)-3-((3-phenyl-1H-pyrazol-5-yl)methylene)indolin-2-one analogs 12(a-u) were obtained as pure solids (yield 75-80%).

According to the analysis of related databases, 7699-18-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kamal, Ahmed; Shaik, Anver Basha; Jain, Nishant; Kishor, Chandan; Nagabhushana, Ananthamurthy; Supriya, Bhukya; Bharath Kumar; Chourasiya, Sumit S.; Suresh, Yerramsetty; Mishra, Rakesh K.; Addlagatta, Anthony; European Journal of Medicinal Chemistry; vol. 92; (2015); p. 501 – 513;,
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. 65826-95-1, name is 5-Methylindoline, A new synthetic method of this compound is introduced below., Product Details of 65826-95-1

EXAMPLE 54 2-(5-Methylindolin-1-yl)benzonitrile A slurry of 5-methylindoline (31 g, 0.23 mole), sodium hydride (11.3 g, 60% in oil) and dimethylsulfoxide (120 ml) was stirred at room temperature for 1 hour. A solution of o-fluorobenzonitrile (31 gm, 0.25 mole) in dimethylsulfoxide (25 ml) was added dropwise at a temperature below 20 C. Upon completion of the addition, the mixture was stirred for 2 hours at room temperture. The reaction mixture was partitioned between methylene chloride (700 ml) and ice-water (700 ml). The dichloromethane solutions were separated. The aqueous phase was extracted with dichloromethane (2 times, 600 ml). The combined dichloromethane solutions were washed with 2N hydrochloric acid (2 times, 500 ml), water (500 ml), brine (2 times, 400 ml), dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was dissolved in ethanol (300 ml) and heptane (100 ml), and chilled in a freezer. The precipitate was collected. The mother liquor was concentrated and purified by flash chromatography on a silica gel column (400 g, 230-400 mesh) eluted with hexane:dichloromethane (3:1, 3 l); hexane:dichloromethane (1:1, 2 l) and dichloromethane (2 l). The fractions containing product were pooled and concentrated to yield 33 g (73% overall yield). The analytical sample was prepared by high-pressure liquid chromatography (Water Associates Prep 500, 10 g, 2 chamber, elution with hexane:dichloromethane, 9:1, 12 l) followed by crystallization from ethanol, mp 59-60 C. ANALYSIS: Calculated for C16 H14 N2: 82.02%C 6.02%H 11.96%N. Found: 82.47%C 6.08%H 12.10%N.

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; Hoechst-Roussel Pharmaceuticals Inc.; US4663453; (1987); A;,
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 675109-26-9 as follows. SDS of cas: 675109-26-9

6-Bromoisoindolin-l-one (4 g, 18.9 mmol) was suspended in 70 ml of THF and cooled to 0-5C. Sodium hydride (60% in mineral oil) (1.5 g, 37.7 mmol, 2 equiv.) was added in portions at 0-5C and after 5 minutes (2RS)-2-bromo-2-phenyl-acetic acid (4.34 g, 20.2 mmol, 1.07 equiv.) were added and the mixture was stirred at 0-5 C for 2 hours. The reaction mixture was extracted with 1M HC1 solution and twice with ethyl acetate. The organic layers were dried over sodium sulfate and evaporated to dryness to obtain the desired (2RS)-2-(6-bromo-l-oxo-isoindolin-2-yl)-2- phenyl-acetic acid (5.78 g, 89 % yield) as a white solid, MS: m/e = 345.9/347.9 (M+H+).

According to the analysis of related databases, 675109-26-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; C4 THERAPEUTICS, INC.; DUPLESSIS, Martin; JAESCHKE, Georg; KUHN, Bernd; LAZARSKI, Kiel; LIANG, Yanke; NAGEL, Yvonne Alice; RICCI, Antonio; RUEHER, Daniel; STEINER, Sandra; (46 pag.)WO2019/149922; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem