Category: indolines-derivatives

Some common heterocyclic compound, 21857-45-4, name is 5-Methoxyindoline, molecular formula is C9H11NO, 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. HPLC of Formula: C9H11NO

Example 44 6,7-Dimethoxy-4-(5-methoxy-2,3-dihydro-indol-1-yl)-quinazoline methanesulfonate salt Utilizing a procedure analogous to that described in Example 1, this product was prepared in 95% yield from 5-methoxy-indoline (1.1 eq.), and 4-chloro-6,7-dimethoxy-quinazoline (1.0 eq) in i-PrOH. The free-base obtained following column chromatography on silica (45% acetone/hexanes) was dissolved in minimal CH2 Cl2 and treated with 1 eq. of methanesulfonic acid in CH2 Cl2 followed by dilution with several volumes of ether to precipitate the mesylate salt which was filtered and added in vacuo. (M.P. 285-292 C. (dec); LC-MS: 338 (MH+); anal. RP18-HPLC RT: 3.82 min.).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 21857-45-4, its application will become more common.

Reference:
Patent; Pfizer Inc.; US5736534; (1998); A;,
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. 64483-69-8, name is 5-Acetylindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Product Details of 64483-69-8

A mixture of 5-acetyl-2-oxindole (70 mg), 3-methylindole-2-carbaldehyde (56 mg) (prepared according to Synthetic Communications, 1986, 16, 1799) and piperidine (30 mg) in ethanol (1 mL) was heated in a sealed tube at 90 C. for overnight. The mixture was cooled to room temperature. The solid was collected by vacuum filtration, washed with cold ethanol and dried in oven for overnight to give 83 mg (75% yield) of 5-acetyl-3-(3-methyl-1H-indol-2-ylmethylene)-1,3-dihydro-indol-2-one. 1H NMR (360 MHz, DMSO-d6) 12.86 (s, br, 1H, NH), 11.29 (s, br, 1H, NH), 8.43 (d, J=1.5 Hz, 1H, H-4), 8.01 (s, 1H, vinyl), 7.78 (dd, J=1.5 and 8 Hz, 1H, H-6), 7.58 (d, J=8 Hz, 1H), 7.45 (d, J=8 Hz, 1H), 7.23 (t, 1H), 7.01 (t, 1H), 6.92 (d, J=8 Hz, 1H), 2.58 (s, 3H, CH3), 2.54 (s, 3H, CH3). MS m/z 317.2 [M+1]+.

The synthetic route of 64483-69-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUGEN, Inc.; US2002/183364; (2002); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 1504-06-9, A common heterocyclic compound, 1504-06-9, name is 3-Methyloxindole, molecular formula is C9H9NO, 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.

The amount of surfactant SDS is increased,30 mol% (ie 28.8 mg) of 3-methyl-2-indanone,The remaining conditions are the same as in Embodiment 1,The yield of the target product 3-methyl-3-hydroxy-2-indanone was 84%.

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; Ningbo University; Bao Wenhui; Wei Wenting; Gao Lehan; Wang Xinye; (12 pag.)CN108409630; (2018); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 16800-68-3, 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. 16800-68-3, name is 1-Acetylindolin-3-one, This compound has unique chemical properties. The synthetic route is as follows.

3 – (2 – Methylphenyl) propyne acid 4 – nitrophenyl-unitz (84.3 mg 0.3 mmol), was obtained. N- Acetylindole -3 -unitz 26.3 mg (0.15 mmol), the carbene-unitz (0.015 mmol), 3.96 mg, 1 diazabicycloundecene 8 – (-7 -) and methylene-methylene chloride shown in Formula 45 mul IV 0.3 mmol were placed in 3 ml a 25 ml unitunito-two-port 2h bottle, and reacted 30 C, under unituniteous conditions, and concentrated, under inert atmosphere protection, unitant-like conditions. The eluate fractions of all the products 10:1 detected were collected by chromatography with petroleum ether: ethyl acetate in the timetime as eluent column chromatography, and the solvent was evaporated to obtain the residue unit, 43 mg and gave rise 91% to unit_.

The chemical industry reduces the impact on the environment during synthesis 1-Acetylindolin-3-one. I believe this compound will play a more active role in future production and life.

Reference:
Patent; China Pharmaceutical University; Du Ding; Sun Kewen; (10 pag.)CN110156800; (2019); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 7477-63-6, name is 7-Chloroisatin, 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 7477-63-6, Computed Properties of C8H4ClNO2

5mmol of o-phenylenediamine in turn,5mmol 7-chlorodione indole,6mmol iodoethane,1mmol p-toluenesulfonic acid,1mmol selective fluorine reagent,20ml of toluene was added to the round bottom flask,Stir at reflux at 70-90 C for 24 hours. After the reaction is complete, add 30 ml of brine to quench the reaction. The reaction mixture is extracted with 90 ml of ethyl acetate three times to extract the reaction product. An analytically pure 7-chloro-6-ethyl-6H-indole [2,3-b] quinoxaline was obtained. Red solid, 81% yield

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 7-Chloroisatin, and friends who are interested can also refer to it.

Reference:
Patent; South China Normal University; Guangzhou Huarui Optoelectric Materials Co., Ltd.; Song Xinlong; Zhou Guofu; Pan Junyou; (10 pag.)CN110283177; (2019); 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 1504-06-9 as follows. COA of Formula: C9H9NO

5-bromo-3-methyl-indol-2-one Under an atmosphere of nitrogen, bromine (0.96 g, 6.0 mmol) in acetic acid (5 cm3). was added drop wise to a solution of 3-methyl-2-indolinone (0.8749 g, 6.0 mmol) (Kende, et al, Synth. Commun., 12, 1, 1982) and sodium acetate (0.50 g, 6.0 mmol) in acetic acid (10 cm3). The reaction was stirred at room temperature for 3.5 h. Saturated sodium carbonate was added to quench the reaction. The water layer was extracted EtOAc (*3), dried (MgSO4), filtered, and evaporated to give the title compound (1.26 g, 93%), Mp=119-120 C.; 1H NMR (DMSO) delta 1.32 (d, 3H, J=7.66 Hz), 3.45 (q, 1H, J=7.62 Hz), 6.77 (d, 1H, J=8.23 Hz), 7.46 (s, 1H), 7.36-7.33 (m, 1H), 10.4 (s, 1H); IR (KBr) 3200, 1725 cm-1; MS (EI) m/z 224/226 (M-H)-; CHN calculated for C9H8BrNO: C, 47.82; H, 3.57; N, 6.20; Found: C, 47.44; H, 3.42; N, 6.04.

According to the analysis of related databases, 1504-06-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Wyeth; Ligand Pharmaceuticals, Inc.; US6462032; (2002); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 25369-33-9, name is 7-Chloroindolin-2-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. Safety of 7-Chloroindolin-2-one

General procedure: A mixture of 2a-j (1.50 mmol) and 5 (1.50 mmol) in ethanol (10 mL) was treated with a catalytic amount of piperidine. The reaction mixture was stirred under reflux until complete consumption of the substituted indolin-2-ones was observed by TLC. After cooling, the precipitate was filtered, recrystallised from absolute ethanol and dried in air to furnish pure (E)-3-(benzothiazol-2-ylmethylene)indolin-2-ones 6a-j.

The synthetic route of 7-Chloroindolin-2-one has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Chao; Xu, Juan; Zhao, Xinyu; Kang, Congmin; Journal of Chemical Research; vol. 41; 9; (2017); p. 537 – 540;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 552330-86-6, These common heterocyclic compound, 552330-86-6, name is 5-Bromoisoindolin-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.

5-Bromo-2,3-dihydro-lH-isoindol-l-one (100 mg, 0.47 mmol) was dissolved in DMF (4.7 mL) and stirred at 0C. NaH (38 mg, 0.94 mmol, 60 wt.% dispersion in oil) was carefully added in two portions, and the resulting mixture was allowed to stir at 0C for 15 minutes before 2,2,2-trifluoroethyl trifluoromethanesulfonate (110 mg, 0.47 mmol) was added. The mixture was allowed to stir at 0C for 30 minutes before saturated aqueous NaHC03 (10 mL) was carefully added, and the mixture was extracted with EtOAc. The organic layer was washed with water, brine, dried over anhydrous MgS04, filtered, and concentrated in vacuo. The residue was purified by silica chromatography, eluting with a 0-20% EtOAc/hexanes gradient. LRMS (ESI) calc’d for Ci0H8BrF3NO [M+H]+: 294, found: 294.

Statistics shows that 5-Bromoisoindolin-1-one is playing an increasingly important role. we look forward to future research findings about 552330-86-6.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DINSMORE, Christopher; FULLER, Peter; GUERIN, David; THOMPSON, Christopher F.; PU, Qinglin; SCOTT, Mark E.; KATZ, Jason David; KURUKLASURIYA, Ravi; CLOSE, Joshua T.; FALCONE, Danielle; BRUBAKER, Jason; ZENG, Hongbo; BAI, Yunfeng; FU, Jianmin; KONG, Norman; LIU, Yumei; ZHENG, Zhixiang; WO2014/146492; (2014); 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., Application In Synthesis of 7-Chloroisatin

The specific steps are:Add 7-chloroindole (54.5 mg, 0.3 mmol) to the pressure tube.Benzamidine hydrochloride (140.9 mg, 0.9 mmol),CuI (5.7 mg, 0.03 mmol)And potassium phosphate (381.6 mg, 1.8 mmol).Add 3mL of DMSO,After magnetic stirring at room temperature for 5 hours,The reaction solution was extracted with dichloromethane.The organic layer was washed with saturated brine.After drying anhydrous sodium sulfate,The solvent is distilled off under reduced pressure to obtain a crude product.The crude product is purified by column chromatography with dichloromethane/petroleum ether=1:20 (V/V) as the eluent to obtain the desired product. The product is a yellow solid.The yield was 68percent.

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; Wuhan Institute of Technology; Jia Fengcheng; Chen Yunfeng; (8 pag.)CN108558782; (2018); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 340702-10-5, A common heterocyclic compound, 340702-10-5, name is 6-Fluoroisoindolin-1-one, molecular formula is C8H6FNO, 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.

To a stirred solution of 6-fluoroisoindolin-1-one (10 g, 66.2 mmol) in anhydrous dichloromethane (100 mL) were added triethylamine (16.72, 165.5 mmol, 21.8 mL), (Boc)2O (17.3 g, 79.4 mmol) and catalytic DMAP (100 mg) at room temperature. The reaction mixture was stirred at room temperature for 16 h. After completion, the reaction mixture was diluted with CH2Cl2, washed with H2O, and then saturated aqueous NaHCO3. The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. The crude compound was purified by silica gel chromatography (0-30% ethyl acetate in hexanes) to give the product. MS: (ES) m/z calculated for C13H14FNO3 [M+H]+ 252.3, found 252.3.

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:
Patent; CHEMOCENTRYX, INC.; CHEN, Xi; DRAGOLI, Dean R.; FAN, Junfa; KALISIAK, Jaroslaw; LELETI, Manmohan Reddy; MALATHONG, Viengkham; McMahon, Jeffrey; TANAKA, Hiroko; YANG, Ju; YU, Chao; ZHANG, Penglie; Mali, Venkat; (62 pag.)US2017/144996; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem