Month: March 2021

Some common heterocyclic compound, 1029691-06-2, name is 2-(3-Oxocyclopentyl)isoindoline-1,3-dione, molecular formula is C13H11NO3, 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. COA of Formula: C13H11NO3

Reference Synthesis Example 221 (0990) 3-(1,3-Dioxoisoindolin-2-yl)cyclopenta-1-en-1-yl trifluoromethanesulfonate (0991) To a dichloromethane solution (30 mL) of 2-(3-oxocyclopentyl)isoindoline-1,3-dione (1.08 g, 4.71 mmol), trifluoromethanesulfonic acid anhydride (1.16 mL, 7.06 mmol) and N,N-diisopropylethylamine (1.16 mL, 9.42 mmol) were added at 0 C. and the resultant mixture was stirred at 0 C. for 1 day. After completion of the reaction, the reaction solution was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1) to obtain the title compound (780 mg, yield 46%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1029691-06-2, its application will become more common.

Reference:
Patent; NISSAN CHEMICAL INDUSTRIES, LTD.; Saito, Noriko; Egi, Jun; Nagai, Hiroshi; Ueno, Megumi; Shintani, Yusuke; Inaba, Yusuke; Adachi, Michiaki; Hirai, Yuichi; Kawazu, Takeshi; Yasutake, Koichi; Takahashi, Daiki; (220 pag.)US9403798; (2016); B2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 7477-63-6, 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. 7477-63-6, name is 7-Chloroisatin belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

In 25 ml sealed tube by adding 1 a (0.5 mmol, 88.6 mg), 2 i (0.5 mmol, 90.8 mg), iodine simple substance (0.25 mmol, 63.5 mg), triethylamine (0.25 mmol, 25.3 mg) and chlorobenzene (2 ml), then put into 130 C in oil bath stirring reaction 10 h. Add 50 ml water quenching reaction, extracted with ethyl acetate (50 ml ¡Á 3), the organic phase after the mass concentration is 10% of Na2 S2 O3 Solution and saturated salt water are successively washing, drying with anhydrous sodium sulfate. Filtering, turns on lathe does, too separating by silica gel column (petroleum ether/ethyl acetate=5/1) to obtain the target product 3 u (79.2 mg, 56%). The compound of the characterization data are as follows:

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, 7-Chloroisatin, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Xinxiang Medical University; Gao Qinghe; Liu Xingxia; Liu Zhaomin; Yang Limin; Yuan Huan; He Shuang; (16 pag.)CN107501180; (2017); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 6941-75-9,Some common heterocyclic compound, 6941-75-9, name is 5-Bromoisoindoline-1,3-dione, molecular formula is C8H4BrNO2, 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.

To a solution of 5-bromoisoindoline-1,3-dione (25.0 g, 0.11 mmol) in THF(1000 mL) were added BH3Me2S (100 mL). The resulting mixture was heated at 80 C for 17h. After LCMS showed the reaction was completed, the reaction mixture was quenched withMeOH and concentrated. The residue was purified by column chromatograph on silica gel(eluted with PE: EA=20:1) to give the title compound (3.98 g, 18.2%). ?HNMR(400MHz, MeOD) 5 7.62 (1 H, s) 7.55 (1 H, d, J=8.0 Hz) 7.35 (1 H, d, J=8.0 Hz) 4.62 (2 H, s)4.58 (2 H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromoisoindoline-1,3-dione, its application will become more common.

Reference:
Patent; KADMON CORPORATION, LLC; KIM, Ji-in; LIU, Kevin; POYUROVSKY, Masha; LU, Dan; ZHU, Zhenping; WO2015/54317; (2015); 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. 897957-06-1, name is 6-Bromo-1-methylindolin-2-one, A new synthetic method of this compound is introduced below., category: indolines-derivatives

To 1-3.2 (91 mg, 0.40 mmol) in anhydrous dioxane (8 mL) is added R5 (155 mg, 0.61 mmol) and potassium acetate (120 mg, 1.22 mmol). The mixture is purged with Argon, [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (PdCl2(dppf)) (33 mg, 0.040 mmol) added and heated to 80 C for 1.5 h. The reaction mixture is diluted with EA and water, the organic layer washed with brine, dried and concentrated. The residue is purified via column chromatography (cyclohexane / EA = 1:1). Yield 100%. m/z 274 [M+H]+, rt 0.71 min, LC-MS Method b.

The synthetic route of 897957-06-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GRUNDL, Marc; OOST, Thorsten; PAUTSCH, Alexander; PETERS, Stefan; RIETHER, Doris; WIENEN, Wolfgang; WO2013/41497; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 181140-34-1, 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. 181140-34-1 name is (R)-(-)-N-(2,3-Epoxypropyl)phthalimide, 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.

To a reaction vessel were added (R)-glycidylphthalimide 5.80 g (28.6 mmol), 4-chloro-2-methoxyphenol 3.17 g (20.0 mmol), potassium carbonate 2.76 g (20 mmol) and DMF 60 mL, and the mixture was stirred at 80 C. for 46 hours. After evaporation of the solvent, to the condensed residue was added 1,2-dichloroethane and the mixture was washed with an aqueous 3% NaOH solution, an aqueous 1% HCl solution and an aqueous 5% NaCl solution successively. The organic layer was taken, and the solvent was evaporated to give (R)-1-(4-chloro-2-methoxyphenoxy)-3-phthalimido-2-propanol 4.20 g (yield 59%, chemical purity 90%) as a pale yellow solid.

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

Reference:
Patent; Miki, Yasushi; Mikami, Masafumi; US2006/19993; (2006); 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. 3335-98-6, name is 1-Phenyloxindole, A new synthetic method of this compound is introduced below., Computed Properties of C14H11NO

General procedure: A mixture of oxindole 1 (0.30 mmol), allenoate 2 (0.75 mmol), PPh3 (0.045 mmol) in xylene (2.0 mL, dried over 4 A MS) was stirred at 50 C under Ar atmosphere for 24 h. After completion of the reaction (indicated by TLC), the mixture was quenched with saturated NaCl solution and diluted with EtOAc, followed by washing with H2O and saturated NaCl solution, and finally dried over Na2SO4. The crude product was purified by flash column chromatography to provide the corresponding product 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:
Article; Zhang, Ji-Quan; Li, Shu-Min; Wu, Chun-Feng; Wang, Xing-Lan; Wu, Ting-Ting; Du, Yao; Yang, Yuan-Yong; Fan, Ling-Ling; Dong, Yong-Xi; Wang, Jian-Ta; Tang, Lei; Catalysis Communications; vol. 138; (2020);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 446292-08-6, name is (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-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 446292-08-6, Recommanded Product: 446292-08-6

10 g (S)-2-((2-oxo-3-(4-(3-oxo-morpholino)phenyl)oxazolidin-5- yl)methyl)isoindoline-l,3-dione of Formula (I), 70 ml methanol and 60 ml monomethyl amine were added to RBF at 25C to 35C. The reaction was heated to 60C to 65C for 1-2 hours. To the reaction mass L (+)-mandelic acid (3.6 g) was added and maintained for 30 minutes. The reaction mass was cooled to 45 to 50C and maintained for 30 minutes. The reaction mass was cooled to 25 to 35C and maintained for 30 minutes. The product was filtered and washed with methanol (50 ml x 2) afforded the L(+)-mandelate salt of (S)-4-(4-(5-(aminomethyl)-2-oxo-oxazolidin- 3-yl)phenyl)morpholin-3-one of Formula (JM).

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; CADILA HEALTHCARE LIMITED; DWIVEDI, Shriprakash, Dhar; PRASAD, Ashok; PAL, Daya, Ram; SHARMA, Mukul, Hari, Prasad; JAIN, Kuldeep, Natwarlal; PATEL, Naitik, Bharatbhai; WO2013/98833; (2013); A2;,
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. 20780-72-7, name is 4-Bromoisatin, A new synthetic method of this compound is introduced below., name: 4-Bromoisatin

General procedure: (The reagents were purchased fromAdamas and used without further purification.) A dry 3-mL flask was chargedwith relevant isatin 5 (0.3 mmol), tert-butyl 2-aminoacetate hydrochloride 7(0.3 mmol) and benzophenone imine 8 (0.36 mmol). The reaction mixture wasstirred at room temperature for the corresponding time. After the completionof the reaction, the reaction mixture was directly purified by silica gelchromatography (ethyl acetate/petroleum ether = 1:4) to give product 6. Asolution of 6 in EA/TFA (10:1) was stirred in a 10-mL flask under roomtemperature for 3 h. The solvent was removed under vacuum. The residue wasrecrystallized in diethyl ether/petroleum ether to give product 9.

The synthetic route of 20780-72-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Huang, Huang; Xu, Yong; Mao, Fei; Zhu, Jin; Jiang, Hualiang; Li, Jian; Tetrahedron Letters; vol. 56; 4; (2015); p. 586 – 589;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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, Quality Control of 5-Bromoisoindoline-1,3-dione

Phthalimide (leq) was added to a solution of 3-bromomethyl-pyridine (1.1 eq) and K2CO3 (2eq) in DMF under N2. The mixture was stirred at rt for 16 hrs. Reaction was diluted in water and the compound precipitated. The solid was filtered and dried under reduced pressure. Compound was used in the next step without further purification.

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; GALAPAGOS NV; MENET, Christel Jeanne Marie; JOUANNIGOT, Nolwenn; BLANC, Javier; VAN ROMPAEY, Luc Juliaan Corina; FLETCHER, Stephen Robert; WO2010/10186; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 3676-85-5, 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. 3676-85-5, name is 5-Aminoisoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A mixture of 4- aminophthalimide (1 .2 mmol), 2,6-dichlorobenzenesulfonyl chloride (1 .2 mmol), trimethylamine (1.4 mmol), and DMAP (cat.) in toluene was heated at 100 C for 72 h. The reaction mixture wasquenched with H20 and extracted with EtOAc. The combined organic layers was dried overNa2SO4 and filtered. Purification via preparative HPLC gave compound 116 in 3% yield. ?HNIVIR(400 1VIHz, DMSO-d6) 11.75 (s, 1H), 11.22 (s, 1H), 7.74 (d, J= 8.1 Hz, 1H), 7.71 -7.64 (m,2H), 7.59 (dd, J= 8.9, 7.1 Hz, 1H), 7.48 -7.36 (m, 2H). ?3C NIVIR (101 MHz, DMSO) 169.04,169.01, 135.08, 135.04, 134.91, 132.60, 127.08, 125.13, 122.59, 111.35.

The synthetic route of 5-Aminoisoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE CENTRE FOR DRUG RESEARCH AND DEVELOPMENT; THE UNIVERSITY OF BRITISH COLUMBIA; ROBERGE, Michel; BARADARAN-HERAVI, Alireza; BALGI, Aruna D.; ZIMMERMANN, Carla D.; KRAUSE, Alexandra; PFEIFER, Thomas Arthur; JAQUITH, James Brian; TAN, Jason Samuel; SHIDMOOSSAVEE, Fahimeh S.; ARNS, Stephen Paul; BAUDELET, Davy Jeremy; (354 pag.)WO2017/49409; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem