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. 32692-19-6, name is 5-Nitroindoline, A new synthetic method of this compound is introduced below., Recommanded Product: 5-Nitroindoline

General procedure: We described the synthesis of the compound 1 (Table 2) to illustrate the general procedure for TFA accelerated Petasis three-component reaction. The descriptions of the preparations of all reported compounds are in the Supporting information section. To a magnetically stirred mixture of 5-nitroindoline (0.164 g, 1.0 mmol), 4-tolyboronic acid (0.135 g, 1.0 mmol), and glyoxylic acid monohydrate (0.092 g, 1.0 mmol) in CH2Cl2 (5 ml) was added TFA (20 mul). The mixture was stirred at room temperature for 4 h. After the completion of the reaction (TLC monitoring), half of the solvent was evaporated by means of a rotovap. The resulting solid was filtered through a sintered glass funnel. The collected solid was thoroughly washed with petroleum ether and a small amount of ice water (5 ml), and then dried in vacuo at room temperature for 24 h to afford 0.26 g (83.3 %) of 2-(5-nitroindolin-1-yl)-2-(p-tolyl) acetic acid as a light yellow 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; Zhang, Jing; Yun, Fan; Xie, Rui; Cheng, Chunhui; Chen, Guangyao; Li, Jingxuan; Tang, Pingwah; Yuan, Qipeng; Tetrahedron Letters; vol. 57; 35; (2016); p. 3916 – 3919;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 924304-73-4, 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. 924304-73-4 name is 4-Chloroisoindoline hydrochloride, 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.

Step 4: Synthesis of (3J?,5S)-1-((S)-4-(but-3-enyIoxy)-2-(tert- butoxycarbonylamino)butanoyl)-5-((li?,25)-1-(ethoxycarbonyl)-2- vinylcyclopropylcarbamoyl)pyrrolidin-3-yl 4-chIoroisoindoline-2-carboxylate[0489] (17?,25)-ethyl l-((25,4i)-1-((5)-4-(but-enyloxy)-2-(tert- butoxycarboalphaylamino)butanoyl)-4-hydroxypyrrolidine-2-carboxamido)-2- vinylcyclopropanecarboxylate (0.55 g, 1.1 mmol) in THF (20 mL) was added 1,1 ‘- carbonyldiimidazole (0.204 g, 1.26 mmol) in one portion. The reaction was stirred at room temperature for 3 hours. To the reaction was then added the N-ethyl-N-isopropylpropan-2- amine (0.92 mL, 5.3 mmol), followed by 4-chloroisoindoline hydrochloride (0.258 g, 1.37 mmo.). The reaction was stirred at 50 C for 18 hours. The solvent was removed. The residue was partitioned between ethyl acetate (20 mL) and saturated sodium bicarbonate solution. The organic layer was separated and dried over sodium sulfate. After removal of solvent, the residue was purified by chromatography (HexanerEthyl acetate=l :3) to give (3i?,5£)-1-((S)-4- (but-3-enyloxy)-2-(tert-butoxycarbonylamino)butanoyi)-5-(( IR,2S)- 1 -(ethoxycarbonyl)-2- vinylcyclopropylcarbamoyl)pyrrolidin-3-yl 4-chloroisoindoline-2-carboxylate as white solid (0.49 g, 66%). MS: Calcd.: 702.3; Found: [M+H]+ 703.1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Chloroisoindoline hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; INTERMUNE, INC.; ARRAY BIOPHARMA, INC.; WO2008/137779; (2008); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 59-48-3, name is Indolin-2-one, molecular formula is C8H7NO, 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. Quality Control of Indolin-2-one

Step 1 Oxindole (20.0 g; 0.15 mol) and lithium chloride (21.0 g; 0.49 mol) were suspended in tetrahydrofuran (400 mL) and the mixture cooled to -78° C. n-Butyllithium (120.0 mL; 0.30 mol, 2.5M in hexanes) was added slowly and the mixture was stirred for 20 minutes, then iodomethane (18.7 mL; 0.30 mol) was added. The mixture was warmed to 25° C., stirred overnight and then quenched with saturated aqueous ammonium chloride and diluted with diethyl ether. The organic layer was washed with water and brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification by flash chromatography (0-20percent ethyl acetate-hexane) afforded 10.0 g (41percent) of 3,3-dimethyl-1,3-dihydro-indol-2-one as a yellow solid. MS (ESI) m/z 162 ([M+H]+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 59-48-3, its application will become more common.

Reference:
Patent; Wyeth; US2007/72897; (2007); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 102359-00-2, A common heterocyclic compound, 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, molecular formula is C9H7NO3, 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 above material was dissolved in methanol (50 mL) and formic acid (5 miL) and hydrogenated over Pd/C (0.40 g) at elevated hydrogen pressure (50 psi) for 16 h. The reaction mixture was filtered through a plug of celite (10 g), the celite was washed with methanol (2X20 ML), the combined filtrates were evaporated to dryness, dissolved in H20 (20 mL), and re-evaporated. The resulting residue was dissolved in N, N-DIMETHYLFORMAMIDE (5 mL), and added in one portion to the previously prepared suspension of 2-oxoindoline-5-carboxylic acid (0.53 g, 3 MMOL), O-(BENZOTRIAZOL-L-YL)-N, N, N, N-TETRAMETHYLURONIUM tetrafluoroborate (1.1 g, 3.6 mmol), 1-HYDROXYBENZOTRIAZOLE (0.486 g, 3.6 mmol) and N,N-diisopropylethylamine (1.7 g, 12 mmol) in acetonitrile (10 ML) and N,N-dimethylformamide (10 mL). The mixture was stirred overnight, the solvents were removed in vacuo, and the residue was purified on a silica gel column using chloroform/methanol, (10: 1), then CHLOROFORM/METHANOL/AQUEOUS ammonia, (100: 10: 1), as the eluent. The semi-solid crude material was again subjected to silica gel chromatography using chloroform/methanol/aqueous ammonia, (150: 10: 1), as the eluent to afford 0.20 g (19% yield) the title compound as yellow foam: MS (ES) M/Z 367 (M++1).

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; ASTRAZENECA AB; WO2005/27823; (2005); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 675109-45-2, 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. 675109-45-2, name is 6-Amino-2,3-dihydro-1H-isoindol-1-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

The starting material was prepared as follows: 6-Amino-2,3-dihydro-isoindol-1-one (0.810 g, CAS 675109-45-2) was dissolved in 12 ml of acetonitrile and treated successively with sodium iodide (2.458 g, 3 eq.), 1,5-dibromopentane (1.11 ml, 1.5 eq.), and N-ethyl-diisopropylamine (2.88 ml, 3.1 eq.), and the mixture was stirred at 75 C. for 20 h. Pouring onto crushed ice, twofold extraction with AcOEt, washing with water and brine, drying over magnesium sulfate, and evaporation of the solvents, followed by crystallization from hexane/ethyl acetate yielded 6-piperidin-1-yl-2,3-dihydro-isoindol-1-one (0.669 g) as light brown crystals, MS 217.3 ([M+H]+).

The synthetic route of 6-Amino-2,3-dihydro-1H-isoindol-1-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Gobbi, Luca Claudio; Zbinden, Katrin Groebke; Mohr, Peter; Obst, Ulrike; US2005/137168; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 774-47-0, 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. 774-47-0, name is 5,6-Difluoroindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A mixture of 5-amimotetrazole (1 mmol, 0.085 g), appropriateisatin (1 mmol), dimedone (1 mmol, 0.14 g) and [MeC(OH)2]+ClO4-(10 mol%) was stirred in EtOH/H2O (1:1, 4 mL) at 80 C. After theindicated time, the reaction was quenched into water (50 mL) andcooled. The precipitated product was separated by centrifugation andpurified by silica gel chromatography to afford the desired product. Allthe products were characterised by melting point, 1H NMR, 13C NMRand LC-MS.

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, 5,6-Difluoroindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Dai, Yong; Qi, Gang; Qian, Xiao-Rong; Journal of Chemical Research; vol. 37; 11; (2013); p. 705 – 708;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 100487-74-9, 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. 100487-74-9, name is 6-Chloro-5-fluoroindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To the mixture of 6-chloro-5-fluoro-1,3-dihydro-indol-2-one (500 mg, 2.7 mmol) and 2-(4-Chloro-2-formyl-phenoxy)-2-ethyl-butyric acid methyl ester (844 mg, 2.97 mmol) (CGENETECH) in methanol (5 mL) was added pyrrolidine (95 mg, 1.35 mmol) dropwise. The mixture was then heated at 70 C. for 1 h. After cooled to room temperature, the mixture was partitioned between EtOAc and diluted HCl. The organic phase was washed with water, brine, dried over anhydrous Na2SO4 and concentrated to give the crude product as a red-yellow solid, which was used for the next step reaction without further purification.

The synthetic route of 6-Chloro-5-fluoroindolin-2-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chen, Li; Han, Xingchun; Wang, Lisha; Wang, Min; Yang, Song; Zhang, Zhuming; US2010/190814; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

3891-07-4, name is 2-(2-Hydroxyethyl)isoindoline-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. Recommanded Product: 3891-07-4

Into the reaction tank, put 350 kg of toluene, stirring temperature, distillation of toluene, after the liquid in the water separator is filled, keep the reflux water for 60 minutes, and take a sample to measure the water, when the water content of the reflux liquid is ?0.2%, the reflux is changed to distillation, distilled 45kg of toluene (worked ethyl 4-chloroacetoacetate as a dilution solvent), stirring and lowering the temperature, when the temperature in the tank drops to 45 C, the reaction tank is filled with nitrogen, continue to cool down at-5 C, under stirring add 40 kg of N-(2-hydroxyethyl)-phthalimide, and the add 20 kg of sodium hydride, after the addition, cover the can lid, stirring at -5 C, into the metering tank draw 38.4 kg of ethyl 4-chloroacetoacetate, 45 kg of toluene and mix well, at -5 C condition added the drops of ethyl 4-chloroacetoacetate toluene solution, the dropping time is controlled at 4 hours, after the addition, the reaction is stirred and the temperature is slowly increased, the temperature of the reaction solution is slowly raised at 32 C within 5 hours, the reaction time is more than 12 hours, and the temperature is raised at 45 C to continue the heat preservation, until the reaction is complete, cool down, control the internal temperature of 25 C, add 61 kg of glacial acetic acid, after the addition, continue stirring to make the material in the reaction solution stir evenly, and the internal temperature is controlled at 25 C, add 180kg of water, add, continue to stir for 30 minutes, stop nitrogen filling, stop stirring, let stand, divide the water layer into the barrel and transfer the toluene layer to the washing tank, transfer the water layer into the reaction tank, into the reaction tank add 75kg of toluene, stir and let stand, the water layer is separated into barrels, and the toluene layer is transferred to a washing tank, the water layer is transferred into the reaction tank, 75 kg of toluene is added into the reaction tank, stirred, and allowed to stand, and the water layer was separated, combine the toluene layer into a water wash tank, add 100kg of 25% salt water to the washing tank, stir for 15 minutes, let stand for 30 minutes, and separate the water layer, obtained 4-[(2-phthalimido) ethyoxyl] ethyl acetoacetate toluene solution

The synthetic route of 3891-07-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Fenglin Biological Technology Co., Ltd.; Zheng Yulin; Chen Yushuang; Gao Huanhuan; Liu Lijuan; Yu Yaoying; (12 pag.)CN108358833; (2018); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 118-29-6, name is 2-(Hydroxymethyl)isoindoline-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. Quality Control of 2-(Hydroxymethyl)isoindoline-1,3-dione

6.1 5-Phthalimidomethyl-2,3,3-trimethylindolenine To a stirred solution of 2,3,3,-trimethylindolenine (20 g, 126 mmol) in concentrated sulphuric acid (100 ml) at ambient temperature was added portionwise N-hydroxymethylphthalimide (20 g, 114 mmol). After 70 hours the reaction mixture was poured onto ice and made basic with concentrated ammonium hydroxide. The resulting precipitate was filtered and dried. The product was obtained as a yellow solid (34.84 g, 87%).

The synthetic route of 2-(Hydroxymethyl)isoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Carnegie Mellon University; US6686145; (2004); 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, Quality Control of 5-Nitroindoline

Example XIV; tert-butyl 5-nitro-2.3-dihvdro-indole-1 -carboxylate; 5 g 5-nitro-2,3-dihydro-1 H-indole are dissolved in 70 ml acetonithle. 7.3 g di- tert-butyl-dicarbonate and 900 mg 4-dimethylaminopyridine are added thereto. After stirring for 24 hours at ambient temperature the mixture is divided between 1 N HCI and ethyl acetate. The aqueous phase is extracted with ethyl acetate and the combined organic phases are washed with saturated sodium hydrogen carbonate solution and saturated sodium chloride solution.After drying with magnesium sulphate the solvents are eliminated in vacuo.The residue is extracted from diisopropylether/petroleum ether.Yield: 6.6 g (82 % of theory) Mass spectrum (ESI+): m/z = 265 [M+H]+

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

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; WO2008/113760; (2008); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem