Tag: M.W=100-200

These common heterocyclic compound, 59-48-3, name is Indolin-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. Computed Properties of C8H7NO

EXAMPLE I 5-acetyl-2-indolinone 171 g (1.28 mol) of aluminium chloride are cooled in 500 ml of 1,2-dichloroethane in the ice bath. Then 78 g (1.1 mol) acetyl chloride are added dropwise, so that the temperature does not exceed 10 C. After 1 h 71.3 g (0.53 mol) 2-indolinone (1,3-dihydro-indol-2-one) are added in 4 batches and the temperature is kept at 10-12 C. The reaction mixture is allowed to come up to ambient temperature slowly overnight. Then the solution is slowly added to 1 kg of ice with vigorous stirring. The slurry is with diluted 1 l water and stirred for another 30 min. Then the precipitate is suction filtered. Yield: 80.9 g (86.3% of theory) Rf=0.36 (silica gel, ethyl acetate/cyclohexane/methanol 9:9:2) C10H9NO2 (MG=175.19) Mass spectrum: m/z=174 (M-H)-

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

Reference:
Patent; Boehringer Ingelheim International GmbH; US2005/203104; (2005); A1;,
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Indoline | C8H9N – PubChem

Reference of 89-40-7,Some common heterocyclic compound, 89-40-7, name is 5-Nitroisoindoline-1,3-dione, molecular formula is C8H4N2O4, 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 synthesis of bromoacetal 6 from phthalimide (7) is shown in FIG. 11. Based on reactions described in the literature, these transformations were carried out on large scale, and some steps were improved. Nitration of 200 g of phthalimide (7) gives 146 g of 5-nitrophthalimide (8). Reduction of 8 by catalytic hydrogenation, according to the literature procedure, is a bottleneck in the synthesis because of the large volume of solvent needed. With a 2 L Parr hydrogenator pressure vessel, 30 g of 8 is converted to 25 g of amine 9. The next step is also a reduction; aminophthalide 10 is obtained quantitatively from 9 by copper-catalyzed reaction with zinc in aqueous base. Steps b and c could be combined by treating 8 with zinc dust and copper(II) sulfate in 2 M aq. sodium hydroxide. This variation, which is not shown in FIG. 11, removes the bottleneck, potentially allowing 100 g of 10 to be prepared in one step from 146 g of 9. The reaction conditions for the steps shown in FIG. 11 are as follows: a) HNO3, H2SO4, 0 C., 56% ; b) 5% Pd/C, H2, EtOAc, 97% ; c) Zn, CuSO4, 6 M NaOH, 5 C. then heated at 70-80 C. 16 h, 100% ; d) NaNO2, 4 M HBr, followed by CuBr at 0 C.; e) DIBAL, toluene, -42 C.; f) BF3 OEt2, MeOH, RT.

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

Reference:
Patent; Bell, Thomas W.; Cline, Joseph I.; Cremo, Christine R.; Gillett, Stephen L.; Frederick, John H.; US2011/77394; (2011); A1;,
Indoline – Wikipedia,
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Reference of 496-12-8, 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 496-12-8 as follows.

Example 17Synthesis of 5-((2,3-dihydrobenzo[b][1,4]dioxin-6-yl)sulfonyl)-2-(phenylsulfonyl)isoindolineReagents MW Reagent/raw material (g/mole) Quantity moles Isoindoline 119.16 0.5 g 4.2 benzenesulfonyl chloride 176.62 1.1 g 6.3 2-(phenylsulfonyl)isoindoline 259.32 0.54 g 2 sulfurochloridic acid 116.52 5 mL excess 2-(phenylsulfonyl)isoindoline-5- 357.83 0.05 g 0.139 sulfonyl chloride 2,3- 136.15 0.024 g 0.18 dihydrobenzo[b][1,4]dioxineAlCl3 133 0.037 0.27 Step 1: Isoindoline was dissolved in 5 mL dry pyridine, and benzenesulfonyl chloride was dropped in. The reaction was stirred overnight at room temperature and an intense red color developed. When complete as determined by HPLC using the protocol of Example 1, as well as by LCMS, the crude reaction mixture was poured into 100 mL cold 1M KHSO4, and extracted twice with 50 mL CH2Cl2. The organic phase was evaporated and the evaporation residue was purified by CombiFlash (PE/EtOAC) providing 1.1 g pure product (100% yield).

According to the analysis of related databases, 496-12-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Becker, Oren M.; Shitrit, Alina; Schutz, Nili; Ben-Zeev, Efrat; Yacovan, Avihai; Ozeri, Rachel; Kehat, Tzofit; Mirilashvili, Sima; Aizikovich, Alex; Sherman, Daniel; Behar, Vered; Kashtan, Osnat; US2012/108631; (2012); A1;,
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Adding a certain compound to certain chemical reactions, such as: 1074-82-4, name is Potassium 1,3-dioxoisoindolin-2-ide, 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 1074-82-4, Application In Synthesis of Potassium 1,3-dioxoisoindolin-2-ide

Under nitrogen atmosphere, 115g of aluminum chloride was added into 750ml of methylene chloride and the slurry mass was cooled to about 0C. lOOg of cis-(+/-)-l- phenyl-3-oxabicyclo[3.1.0]hexan-2-one, compound of formula VI was added at about 0C and the reaction mixture was stirred for about 30min at about 10C. Then diethyl amine solution (125.8g of diethyl amine in 200ml of methylene chloride) was added to the reaction mixture at about 10C to about 15C over a period of 45min and the reaction mixture was stirred for about 60min at about 10C to about 15C. Then 1800ml of water was added to the reaction mixture at about 10C to about 20C over a period of about 30min and stirred for about 2h at about room temperature. 25g of Hyflo was added and stirred for about lOmin. The reaction mixture was filtered through Hyflo bed and the Hyflo bed was washed with 100ml of methylene chloride. The organic layer was separated and taken into a clean container. The aqueous layer was again extracted with 300ml of methylene chloride; where a second organic layer was obtained. The combination of the organic layers was washed with 500ml of water followed by washing with 500ml of 10% aqueous sodium chloride solution, then the organic layer was treated with 50g of sodium sulphate. The organic layer was taken into a round bottomed flask and was cooled to 15C and 95.75 gm of thionyl chloride was slowly added at about 15C to about 20C over a period of about 30min and the reaction mixture was stirred for about 30min at about 15C to about 20C. The reaction mass was cooled to about 0C and 319g of potassium phthalimide was added, the temperature was raised to about 40C to about 45C and stirred at same temperature for about lh, then the reaction mass was cooled to about 10C to about 15C. Then 2.5 liters of 4% aqueous sodium hydroxide solution was added to the reaction mixture at about 10C to about 20C and stirred for about 30min. The aqueous and organic layers were separated and the organic layer was washed 4 times with 700ml each of water and solvent of the organic layer was distilled out completely under vacuum. 200ml of methanol was added to the residue mass at about 35C to about 40C and stirred for about lOmin. Then methanol was distilled out completely under vacuum. Then, 600ml of methanol was added to the residue mass and the temperature was raised to about 65 C and stirred for about 30min. The reaction mixture was cooled to about 20C to about 25C and stirred for about 2h. The precipitated product was filtered and washed with 100ml of chilled methanol. The wet cake was added to 1500ml of water and the slurry was stirred at about 55C to about 60C for about 2h. The solid was filtered at about the same temperature and washed with 500ml of water. The wet cake was added to 350ml of acetone and heated about reflux temperature, then 5g of activated charcoal was added to the clear solution and maintained reflux for about 30min. The reaction mass was filtered through Hyflo bed and the bed was washed with 30ml of acetone. Slowly the clear solution was cooled to about room temperature over a period of lh. Solid was precipitated out and the slurry was maintained for about lh at about room temperature. The solid was filtered out and washed with 50ml of chilled acetone. The compound was dried at about 50C to about 55C for about 15h to yield 1 lOg of the title compound.Purity by HPLC: 99.2%

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, Potassium 1,3-dioxoisoindolin-2-ide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLENMARK GENERICS LIMITED; JAMBUKAR, Nagambar Genuji; GHARPURE, Milind; SINARE, Sudam Nanabhau; THOMBRE, Pravin Chhaburao; KHAN, Mubeen Ahmed; WO2011/158249; (2011); A1;,
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Indoline | C8H9N – PubChem

Related Products of 19727-83-4, 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. 19727-83-4, name is 6-Nitroindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 6-nitroindoline (5.00 g, 30.5 mmol) in CH2C12 (100 mL) was added Et3N (4.25 mL, 3.08 g, 30.5 mmol) and TFAA (4.23 mL, 6.40 g, 30.5 mmol) and the resulting solution stirred at RT for Ih. More Et3N (4.25 mL, 3.08 g, 30.5 mmol) and TFAA (4.23 mL, 6.40 g, 30.5 mmol) were added and the solution was stirred at RT for another 2h. Water (100 mL) was added and the mixture was extracted with CH2C12 (3×100 mL), dried (MgSO4), and concentrated to yield 2,2,2-trifluoro-1-(6-nitroindolin-1- yl)ethanone (8.9 g, crude yield > 100%) as a yellow-brown 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, 6-Nitroindoline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; DECIPHERA PHARMACEUTICALS, LLC; WO2006/71940; (2006); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 14192-26-8, These common heterocyclic compound, 14192-26-8, name is Methyl 2-oxoindoline-6-carboxylate, 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.

(Roth GJ, et al. J Med Chem.2009;52(14):4466-4480). Indolinone 1 (1000 mg, 52.3 mmol) was suspended in acetic anhydride (10 mL) and refluxed at 130 oC for 8 h. The reaction mixture was allowed to cool to 50 oC and (triethoxymethyl)benzene (2930 mg, 131 mmol) was added. The resulting reaction mixture was stirred at 120 oC for 6 h. Then, volatiles were removed in vacuo and petroleum ether was added to the obtained residue. After triturating for 15 minutes, the separated solids were filtered and washed with petroleum ether and then dried under vacuum to afford 974 mg (51%) of title compound.1H NMR (400 MHz, DMSO-d6): delta 8.75 (s, 1H), 8.10 (d, J = 8.0 Hz, 1H), 7.89 (d, J = 8.0 Hz, 1H), 7.49-7.58 (m, 5H), 4.01 (q, J = 7.2 Hz, 2H), 3.87 (s, 3H), 2.44 (s, 3H), 1.35 (t, J = 8.0 Hz, 3H). HRMS m/z found 365.1260, calcd for C21H19NO5 [M]+ 365.1263.

Statistics shows that Methyl 2-oxoindoline-6-carboxylate is playing an increasingly important role. we look forward to future research findings about 14192-26-8.

Reference:
Patent; BOARD OF REGENTS, THE UNIVERSITY OF TEXAS SYSTEM; DALBY, Kevin N.; EDUPUGANTI, Ramakrishna; TALIAFERRO, Juliana; LEE, Juhyeon; (0 pag.)WO2018/160967; (2018); A1;,
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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. 16800-68-3, name is 1-Acetylindolin-3-one, A new synthetic method of this compound is introduced below., Computed Properties of C10H9NO2

The N- acetyl-3-indolyl-one 1.75g (10mmol), N- methyl-5-bromo – indole 2.08g (10mmol) and copper triflate 0.18g (0.5mmol) was dissolved in 1, 1,2-dichloroethane, heated to 120 degrees C, the reaction after 16 hours, extracted with methylene chloride, the organic layers combined, dried over anhydrous sodium sulfate, methylene chloride / methanol to give a white solid product N- acetyl-3 – (of N- -3-methyl-5-bromoindole) – indole 3.37g, yield 92%

The synthetic route of 16800-68-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sun Yat-sen University; Weng, Jiang; Lu, Gui; Guo, Jing; (7 pag.)CN105669516; (2016); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 3676-85-5, A common heterocyclic compound, 3676-85-5, name is 5-Aminoisoindoline-1,3-dione, molecular formula is C8H6N2O2, 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 mixture of 1-(8-(5,6-dimethoxypyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)piperidine-3-carboxylic acid (500 mg, 1.26 mmol), 5-aminoisoindoline-1,3-dione (250 mg, 1.51 mmol) and pyridine (10 mL) was stirred at 0 C. for 2 h. POCl3 (20 drops) was added and stirred for 10 mins, then water (5 mL) was added and the mixture extracted with ethyl acetate (10 mL). The organic layer was washed with brine (10 mL), then dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by prep-HPLC (Gemini 5u C18 150¡Á21.2 mm; inject volume: 3 mL/inj, flow rate: 20 mL/min; wavelength: 214 nm and 254 nm; gradient conditions: 20% acetonitrile/80% water (0.1% TFA, v/v) initially, proceeding to 50% acetonitrile/50% water (0.1% TFA, v/v) in a linear fashion over 9 min) to give the product. HCl (1 mL) was added and then the mixture concentrated in vacuo to give 1-(8-(5,6-dimethoxypyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)-N-(1,3-dioxoisoindolin-5-yl)piperidine-3-carboxamide hydrochloride (10 mg, 2%). 1H NMR (300 MHz, DMSO): delta 11.23 (s, 1H), 10.65 (s, 1H), 10.21 (s, 1H), 8.15 (s, 2H), 7.98 (s, 1H), 7.86 (d, 1H, J=8.4 Hz), 7.77 (d, 1H, J=7.8 Hz), 7.43 (d, 1H, J=8.1 Hz), 6.93 (d, 1H, J=8.1 Hz), 4.29 (d, 1H, J=11.7 Hz), 4.14 (d, 1H, J=12.3 Hz), 3.91 (s, 3H), 7.56 (s, 3H), 3.23-3.02 (m, 2H), 2.73 (s, 1H), 2.10-2.06 (s, 1H), 1.82-1.75 (m, 3H). LC-MS: [M+H]+, 543, tR=1.406 min, HPLC: 98.08% at 214 nm, 98.69% at 254 nm, tR=5.25 min.

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

Reference:
Patent; Hoffmann-La Roche Inc.; Hermann, Johannes Cornelius; Kuglstatter, Andreas; Lucas, Matthew C.; Padilla, Fernando; Wanner, Jutta; Zhang, Xiaohu; US2013/109661; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 317-20-4, name is 7-Fluoroisatin, molecular formula is C8H4FNO2, 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: C8H4FNO2

General procedure: To a pyrex reaction vessel containing a solution of isatin 1a (147 mg, 1.0 mmoL) and NaAuCl4.2H2O (7.95 mg, 2 mol%) in EtOH (1 mL) was added 4-hydroxycoumarin 2 (324 mg, 2.0 mmoL). The resulting mixture was stirred at 40 C for 15 min under microwave irradiation (power level of 200 W). After completion of the reaction as evidenced by TLC, the mixture was cooled to room temperature and poured into ice-cold water (10 mL). The solid obtained was collected by filtration and washed with copious amount of cold water and dried under vacuum at 40 oC for 15 min to afford 251 mg of analytically pure product 3a.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 317-20-4, its application will become more common.

Reference:
Article; Parthasarathy; Praveen, Chandrasekar; Jeyaveeran; Prince; Bioorganic and Medicinal Chemistry Letters; vol. 26; 17; (2016); p. 4310 – 4317;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

110568-64-4, name is 6-Nitroisoindolin-1-one, 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. Safety of 6-Nitroisoindolin-1-one

5-Amino-2,3-dihydroisoindol-l-oneH2N; [693] Iron powder (158mg, 2.83mmol), water (61uL), and HC1 (37%, 5uL,0.566mmol) were added into the suspension of 5-nitro-2,3-dihydroisoindol-l-one (50.4mg,0.283mmol) in EtOH (754|^L). The above mixture was heated at 95C for 2h. After thattime, several drops of 7N NH3 in MeOH were added to basify the solution, and the solid wasfiltered off. The filtrate was concentrated in vacua to obtain a light-yellow solid that waspurified by preparative TLC eluting with 10% MeOH/CH2Cl2 to give a light-yellow solid of5-amino-2,3-dihydroisoindol-l-one. ‘HNMR (CD3OD, 400 MHz): 5 = 7.48 (s, 1 H), 8.08 (s,2 H), 9.91 (s, 1 H), 10.66 (d, 1 H, J= 8.8 Hz). MS (ES+): m/z 149.21 (100) [MH1″]. HPLC: *R= 1.20 min (ZQ2000, polar_5 min).

The synthetic route of 110568-64-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; OSI PHARMACEUTICALS, INC.; WO2006/17443; (2006); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem