Tag: M.W=100-200

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. 14389-06-1, name is 5-Chloro-7-methylindoline-2,3-dione, A new synthetic method of this compound is introduced below., HPLC of Formula: C9H6ClNO2

C. 5-Chloro-7-methyl-1 H-indole5-Chloro-7-methyl-1 H-indole-2,3-dione (1.8g, 9.23mmol) is added neat to a 1.0 M solution of lithium aluminum hydride in ether (92mL). The reaction mixture is stirred at room temperature overnight. The reaction mixture is quenched with ice and is diluted with ethyl acetate (60OmL). The organic phase is collected, washed with sat NH4CI (2 XI OOmL) and brine (50 mL). The organic is dried over magnesium sulfate, filtered and concentrated in vacuo to give the crude product. Purification by flashchromatography on SiO2 eluting with 5% ethyl acetate/ heptane gives 1.27 g, (83% yield) of desired product. 1H-NMR (CDCI3, 300 MHz): delta 8.1 (bs, H), 7.45 (s, 1 H), 7.2 (d, 1 H), 7.0 (s, 1 H), 6.5 (d, H), 2.5 (s, 3H). LCMS m/z: [M+H]+=166

The synthetic route of 14389-06-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANOFI-AVENTIS; CHOI-SLEDESKI, Yong-Mi; GARDNER, Charles, J.; LIANG, Guyan; POLI, Gregory, B.; SHUM, Patrick, Wai-Kwok; STOKLOSA, Gregory, T.; ZHAO, Zhicheng; WO2011/22449; (2011); 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. 7477-63-6, name is 7-Chloroisatin, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C8H4ClNO2

In a 100 mL round bottom flask, according to the feed ratio (7-chloroisatin: methanol (1:1.5); 7-chloroisatin: 1,3-diphenylpropanedione (1:1.2))Add 7-chloroisatin 80 mg (0.44 mmol), methanol 21.1 mg (0.66 mmol) and 1,3-diphenylpropanedione 118.7 mg (0.53 mmol), respectively.A catalytic amount (0.1-fold equivalent of 7-chloroisatin) was added to 001¡Á7FC, ferrocene and palladium acetate, and 25 mL of solvent tetrahydrofuran was heated to 90 ¡ã C, and the reaction was heated for 6 hours.The reaction was monitored by thin layer chromatography. After the reaction was completed, the heating was stopped, the condensing device was removed, the mixed system was concentrated under reduced pressure, and purified by column chromatography.The title compound (8) was obtained by drying to give 83.3 mg,yield of 76percent.

According to the analysis of related databases, 7477-63-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shaanxi University of Science and Technology; Liang Chengyuan; Tian Danni; Ding Shunjun; Wang Xuechuan; Dong Hao; Wang Qiang; (15 pag.)CN108395438; (2018); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 16800-68-3, The chemical industry reduces the impact on the environment during synthesis 16800-68-3, name is 1-Acetylindolin-3-one, I believe this compound will play a more active role in future production and life.

3 – (4 -chlorophenyl) propyne acid 4 – nitrophenyl-unitz (90.3 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, 31 mg and gave rise 62% to unit_.

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, 1-Acetylindolin-3-one, other downstream synthetic routes, hurry up and to see.

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

Reference 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.

A solution of 4-formylbenzene sulfonyl chloride (1) (0.50 g, 2.44 mmol) in dichloromethane (5 mL) was treated with isoindoline (0.32 g, 2.68 mmol) and triethylamine (0.41 mL, 2.93 mmol). The resultant mixture was stirred at room temperature for 1 h. A saturated aqueous solution of sodium bicarbonate (10 mL) was added. The product was extracted three times with 10 mL of dichloromethane. The combined organic layers were dried over potassium carbonate, filtered and concentrated in vacuo. The crude material (0.67 g, 96% yield) was used in the next reaction without purification: Crude 1H NMR (400 MHz, CDCl3) delta 10.06 (s, IH), 8.05-8.00 (m, 4H), 7.25-7.20 (m, 2H), 7.20-7.14 (m, 2H), 4.66 (s, 4H); ESI+ MS: m/z (rel intensity) 288.0 (100, [M+H]+).

The synthetic route of 496-12-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; METASTATIX, INC.; WO2008/109154; (2008); 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. 21857-45-4, name is 5-Methoxyindoline, A new synthetic method of this compound is introduced below., Safety of 5-Methoxyindoline

Part B 5-Methoxyindoline and di-tert-butyl dicarbonate (8.95 g, 1.2 eq.) were stirred in THF overnight at room temperature. The solution was concentrated in vacuo and recrystallized from Et2O/hexane to give 1-(tert-Butoxycarbonyl)-5-methoxyindoline (6.25 g, 74% yield for two steps).

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; DuPont Pharmaceuticals Company; US6245769; (2001); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 32692-19-6, name is 5-Nitroindoline, 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 32692-19-6, Safety of 5-Nitroindoline

General procedure: In a 2-neck RBF, 1 (20 mg, 0.0005 mmol) and TMNO (45 mg, 0.6 mmol) were suspended in toluene (4 mL) and to this solution indoline (60 mg, 0.5 mmol) was added. The reaction mixture was then heated to 100 oC for 20 h and it was filtered and solvent evaporated. The crude product obtained was purified by column chromatography using hexane/ethylacetate (7:1) as eluent to give pure indole (47 mg, 79%). A similar procedure was used for the other indolines and N-heterocycles.

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:
Article; Kumaran, Elumalai; Leong, Weng Kee; Tetrahedron Letters; vol. 59; 44; (2018); p. 3958 – 3960;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 16800-68-3, name is 1-Acetylindolin-3-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. name: 1-Acetylindolin-3-one

Butyl -2 -acetylenic acid 4 – nitrophenyl-unit (61.5 mg 0.3 mmol), was used. 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 3h 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, 24 mg and gave rise 68% to unit_.

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

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

3676-85-5, name is 5-Aminoisoindoline-1,3-dione, belongs to indolines-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. category: indolines-derivatives

A solution of 400 mg (1.44 mM) of 4-chloro-6,7-diethoxy-quinoline-3-carbonitrile and 305 mg (1.88 mM) of 4-Aminophthalimide in 10 ml of ethanol was refluxed for 3 hours. To the warm solution was added 1 ml of 1M sodium carbonate and the sample was heated for 5 minutes at 100C, then poured into 300 ml of ice water. The solid was collected, washed with water followed by ether and dried under vacuum at 80C to yield 348 mg of 4-(1,3-Dioxo-2,3-dihydro-1H-isoindol-5-ylamino)-6,7-diethoxy-quinoline-3-carbonitrile as a yellow solid: mass spectrum (electrospray, m/e): M+H 402.9, mp = 248-251C.

The synthetic route of 3676-85-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wyeth Holdings Corporation; EP1117659; (2003); B1;,
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 41910-64-9 as follows. name: 4-Chloroindoline

To a mixture of 4-chloroindoline (3 g, 19.53 mmol) in H20 (3 mL) was added 2- hydroxyacetonitrile (1.988 mL, 20.51 mmol). The reaction was heated at 105 C for 15 h. The mixture was diluted with EtOAc. The organics were washed with H20, dried over Na2S04, filtered, and concentrated. The residue was purified by silica gel column chromatography to give the title compound (3.3 g). LCMS m/z = 192.8 [M+H]+; NMR (400 MHz, CD3OD) delta ppm 3.02 (t, J = 8.2 Hz, 2H), 3.46 (t, J = 8.2 Hz, 2H), 4.28 (s, 2H), 6.60 (d, J = 2.1 Hz, 1H), 6.76 (d, J = 8.0Hz, 1H), 7.09 (t, J = 8.0 Hz, 1H).

According to the analysis of related databases, 41910-64-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; SEMPLE, Graeme; BEHAN, Dominic P.; FEICHTINGER, Konrad; GLICKLICH, Alan; GROTTICK, Andrew J.; KAM, Maria Matilde Sanchez; KASEM, Michelle; LEHMANN, Juerg; REN, Albert S.; SCHRADER, Thomas O.; SHANAHAN, William R.; WONG, Amy Siu-Ting; ZHU, Xiuwen; WO2015/66344; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

1914-02-9, name is 3,3-Dimethylindoline, belongs to indolines-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. COA of Formula: C10H13N

4a. 3,3-dimethyl-1-(3-nitropyridin-2-yl)indoline:; To 2a (90 mg, 0.61 mmol) was added 2-nitro-3-chloropyridine (200 mg, 1.26 mmol). The reaction mixture was heated at 220 C. microwave for 15 min. The desired compound was isolated via preparative HPLC to afford 4a (30 mg, 18%) as white lyophilizes. Column: Luna 25¡Á100 mm; Eluted from 35% CH3CN to 100% CH3CN in H2O with 0.1% TFA MS (ES) m/z 269 [M+H]+.

The synthetic route of 1914-02-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bristol-Myers Squibb Company; US2006/293281; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem