Month: December 2020

Related Products of 4403-36-5, 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. 4403-36-5 name is 2-(1,3-Dioxoisoindolin-2-yl)ethanesulfonylchloride, 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.

Triethylamine (50 muL), DMAP (catalytic amount) and 2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl) -ethanesulfonyl chloride (27.4 mg, 0.10 mmol) were added to 0.034 mmol 45. The reaction mixture was stirred at room temperature for 18 hours under an inert atmosphere. The reaction was monitored by TLC (EtOAc/hexane 3/7) (Rf 44 = 0.5, Rf45 = 0, Rf 268 = 0.4) and LC/MS. After completion of the reaction, the mixture was diluted with EtOAc (20mL) and washed with 1N HCl, saturated NaHCO3 and brine. The organic phase was dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (ethylacetate/hexane-3/7) to afford 2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethanesulfonic acid 9-benzhydryloxy-7-(4-fluoro-benzyl)-8-oxo-7,8-dihydro-6H-pyrrolo[3,4-g]quinolin-5-yl ester 268 (12.2 mg, 50%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(1,3-Dioxoisoindolin-2-yl)ethanesulfonylchloride, and friends who are interested can also refer to it.

Reference:
Patent; Gilead Sciences, Inc.; WO2004/35576; (2004); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 20870-78-4, 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. 20870-78-4, name is 5-Bromoindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

5-bromoindolin-2-one (1.50 g; 6.93 mmol; 1.00 eq) was dissolved in THF (45.00 ml) then di-ferf-butyl dicarbonate (2.29 g; 10.40 mmol; 1.50 eq) and NaHC03 (5.24 g; 62.41 mmol; 9.00 eq) were added. The mixture was stirred 3h under reflux. Solids were filtered and the filtrate was concentrated. The residue was purified by chromatography (gradient from 100% n-heptane to 80/20 n-heptane / EtOAc) to give tert-butyl 5-bromo-2-oxo-indoline-1-carboxylate (1.52 g; 71 %) as a white solid.

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-Bromoindolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Eng Bang Tiba; Ba Seu-ma-tin; Kon Tal-sil-bi-e; Ju Ni-en-jang—ru-i-seu; Ma Sa-reu-di-e-reu-keu-ri-seu-tin; Mon Tal-be-ti-keu-ri-seu-chan; Su Deu-an-ne; (111 pag.)KR2019/137803; (2019); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 5428-09-1, These common heterocyclic compound, 5428-09-1, name is 2-Allylisoindoline-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.

General procedure: A magnetically stirred solution of N-allylphthalimide 4 (1 equiv) and a xanthate 3 (2-4 equiv) in 1,2-dichloroethane (2-4 mL/mmol of N-allylphthalimide) was heated at reflux for 15 min. DLP (3-5 mol percent) was added and additional DLP (5 mol percent) was added per hour until complete consumption of 4. The mixture was allowed to cool to room temperature and the solvent was evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel to yield the desired product 5.#10;

Statistics shows that 2-Allylisoindoline-1,3-dione is playing an increasingly important role. we look forward to future research findings about 5428-09-1.

Reference:
Article; Kakaei, Saeed; Chen, Ning; Xu, Jiaxi; Tetrahedron; vol. 69; 1; (2013); p. 302 – 309;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 6341-92-0, name is 6-Chloroisatin belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 6-Chloroisatin

General procedure: A mixture of substituted isatin (12.3 mmol), hydrazine hydrate (368 mmol), potassium hydroxide (245 mmol), and ethylene glycol (242 mmol) were heated at 100 C for 1 h. The reaction mixture was cooled on ice bath and acidified using concd HCl (drop wise addition) along with vigorous stirring. The precipitated product was vacuum filtered and washed with hexanes to give substituted indolin-2-ones in 90-95% yield.

The synthetic route of 6341-92-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Jha, Mukund; Chou, Ting-Yi; Blunt, Brian; Tetrahedron; vol. 67; 5; (2011); p. 982 – 989;,
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. 25369-33-9, name is 7-Chloroindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 7-Chloroindolin-2-one

1-(7-Chloro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-6,7-dihydro-2H-pyrano[3,4-c]pyrrol-4-one 7-Chloro-1,3-dihydro-indol-2-one was condensed with 4-oxo-2,4,6,7-tetrahydro-pyrano[3,4-c]pyrrole-1-carbaldehyde to give the title compound. MS m/z 315.2 [M++1].

According to the analysis of related databases, 25369-33-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Tang, Peng Cho; Miller, Todd A.; Li, Xiaoyuan; Zhang, Ruofei; Cui, Jinrong; Huang, Ping; Wei, Chung Chun; US2002/42427; (2002); 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. 114041-16-6, name is 5,6-Dimethoxyisoindoline, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C10H13NO2

A solution of 5,6-dimethoxyisoindoline 10e (0.20 g, 1.13 mmol) in 1,2-dichloroethane (6 mL) is vigorously stirred with 37% aqueous formaldehyde (1.9 mL, 26 mmol) for 5 min. Sodium triacetoxyborohydride (0.72 g, 3.4 mmol) is added in 6 portions over 5 min. The resulting mixture is stirred at room temperature for 3 h. Saturated sodium bicarbonate and dichloromethane are added to the reaction mixture, and the layers are separated. The aqueous layer is extracted with additional dichloromethane (3*). The combined organic phases are washed with water and then brine, dried over Na2SO4 and concentrated under reduced pressure to give crude compound 10f (0.21 g, 100%) as a light-brown solid, m/z=194, [M+H]+

According to the analysis of related databases, 114041-16-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Gladius Pharmaceuticals, Inc.; SUTTON, Larry D.; ZAMBONI, Robert; BUREAU, Patrick; HASSANPOUR, Avid; MAMANI LAPARRA, Laura; VIDAL, Marc; WOO, Simon; ZHOU, Nancy; KEENAN, Richard M.; (127 pag.)US2019/100534; (2019); 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. 959235-95-1, name is 6-(Trifluoromethoxy)indoline, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C9H8F3NO

A mixture of 6-(trifluoromethoxy)indoline [CAS 959235-95-1] (2 g, 9.84 mmol), 2- (4-fluoro-2-methoxyphenyl)acetic acid [CAS 886498-61 -9] (2.17 g, 10.8 mmol), HATU (5.62 g, 14.8 mmol) and diisopropylethylamine (4.9 mL, 29.5 mmol) in DMF (20 mL) was stirred at room temperature for 3 h. Water and ice were added and the precipitate was filtered off and dried to give 2-(4-fluoro-2-methoxyphenyl)-1 -(6- (trifluoromethoxy)indolin-1 -yl)ethanone 6a (3.44 g).

According to the analysis of related databases, 959235-95-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICALS, INC.; KATHOLIEKE UNIVERSITEIT LEUVEN; BONFANTI, Jean-Francois; KESTELEYN, Bart, Rudolf, Romanie; BARDIOT, Dorothee, Alice, Marie-Eve; MARCHAND, Arnaud, Didier, M; COESEMANS, Erwin; DE BOECK, Benoit, Christian, Albert, Ghislain; RABOISSON, Pierre, Jean-Marie, Bernard; (79 pag.)WO2018/215316; (2018); 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. 7477-63-6, name is 7-Chloroisatin, A new synthetic method of this compound is introduced below., category: indolines-derivatives

General procedure: Step 1: To a 250 mL flask equipped with a silicone oil bubbler was added commercially available isatin (7.7 g, 50 mmol) and anhydrous DMF (80 mL). the mixture was cooled down to 0 oC. To this solution was added NaH (1.32 g, 55 mmol), followed by the addition of CH3I in 15 min. Upon completion of the reaction (monitored by TLC), the mixture was diluted with saturated NH4Cl solution and extracted with ethyl acetate. The organic layer was washed with water, dried over Na2SO4, filtered, and concentrated to yield the crude N-methylindoline-2, 3-dione, which was used directly in the next step. Step 2: The N-methylindoline-2, 3-dione (7.58 g, 47 mmol) was refluxed in NH2¡¤NH2-H2O ( 35 %) for 1h. Then the mixture was cooled to rt. The crude product was extracted with ethyl acetate. The combined organic layer was then dried over Na2SO4, purified by flash chromatography on silica gel (petroleum ether/ethyl acetate = 10:1). 1-Methylindolin-2-one was obtained as a pink solid.

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; Zhao, Jian-bo; Ren, Xinfeng; Zheng, Bu-quan; Ji, Jian; Qiu, Zi-bin; Li, Ya; Journal of Fluorine Chemistry; vol. 215; (2018); p. 44 – 51;,
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. 334952-09-9, name is 2-Oxoindoline-6-carboxylic acid, A new synthetic method of this compound is introduced below., name: 2-Oxoindoline-6-carboxylic acid

[00114] To a solution of 2-oxo-2,3-dihydro-lH-indole-6-carboxylic acid (0.20 g,1.1 mmol) in DMF (1 ml) is added N-(3-amino-phenyl)-benzamide (0.26 g, 1.2 mmol), N,N-diisopropylethylamine (0.44 g, 3.4 mmol) and HATU (0.47 g, 1.24 mmol). The reaction is stirred for 20 hours and concentrated. The residue is purified by HPLC (C1S column, eluted with CH3CN-H2O containing 0.05% TFA) to give 2-oxo-2,3-dihydro-lH- indole-6-carboxylic acid (3-benzoylamino-phenyl)-amide as off-white solid. This amide (15 mg, 0.04 mmol) is then heated with lH-pyrrole-2-carbaldehyde (6.0 mg, 0.06 mmol) in ethanol (2 ml) in the presence of 2 drops of piperidine at 8O0C for 20 hours. The mixture is concentrated and the desired compound is obtained after HPLC purification: 1H NMR (DMSO-de) delta 6.41 (s, IH), 6.93 (s, IH), 7.31 (t, IH, J = 7.8 Hz), 7.44 (s, IH), 7.48-7.51 (m, 3H), 7.54 (t, 2H, J = 7.2 Hz), 7.59 (d, IH, J = 6.6 Hz), 7.70 (d, IH, J = 8.4 Hz), 7.78 (d, IH, J = 8.4 Hz), 7.92 (s, IH), 7.98 (d, 2H, J = 7.2 Hz), 8.33 (s, IH), 10.27 (s, IH), 10.31 (s, IH), 11.13 (s, IH), 13.38 (s, IH); LC-MS: 449.1 (MH+).

The synthetic route of 334952-09-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IRM LLC; WO2006/52936; (2006); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 6872-06-6,Some common heterocyclic compound, 6872-06-6, name is 2-Methylindoline, molecular formula is C9H11N, 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.

Pd(OAc)2 (1.12 mg, 0.005 mmol), Zn(OTf)2 (3.63 mg, 0.01 mmol) were dissolved in 5 mL acetonitrile in a glass tube, after stirring for 10 min, indoline (60 mg, 0.5 mmol) were added. The glass tube was equipped with a reflux condenser. Next, the reaction solution was magnetically stirred at 353K in oil bath for 6 h with O2 balloon. The product analysis was performed by GC using the internal standard method. Control experiments including using Pd(OAc)2, or Zn(OTf)2 alone were carried out in parallel.

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

Reference:
Article; Lou, Chenlin; Qin, Shuhao; Zhang, Sicheng; Lv, Zhanao; Senan, Ahmed M.; Chen, Zhuqi; Yin, Guochuan; Catalysis Communications; vol. 90; (2017); p. 5 – 9;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem