Month: August 2021

Application of 2058-72-2, These common heterocyclic compound, 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-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.

A mixture of 2- (1-benzyl-2-oxoindol-3-yl) acetic acid67.4 mg (0.24 mmol),5-Bromo-1-methyl isatin 47.7mg (0.2mmol),N, N’-2- (7-benzo benzotriazole) -N, N, N ‘, N’-tetramethyluronium hexafluorophosphate (106.4 mg, 0.28 mmol)Triethylamine 50.6 mg (0.5 mmol)And 2 mL of tetrahydrofuran were placed in a 25 mL two-necked flask,Reaction at 0 C for 6 h,The reaction solution was concentrated,Eluting with a mixed solvent of petroleum ether: ethyl acetate ratio of 3: 1 as elution column,Collecting the eluted fraction of all the products detected,Rotate the solvent to give the product 90.3mg,The yield was 90% and the Dr value was 4: 1.

Statistics shows that 5-Bromo-1-methylindoline-2,3-dione is playing an increasingly important role. we look forward to future research findings about 2058-72-2.

Reference:
Patent; China Pharmaceutical University; Du Ding; Cao Jing; Dong Shuding; (14 pag.)CN106749295; (2017); A;,
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These common heterocyclic compound, 18711-13-2, name is 4,7-Dichloroindoline-2,3-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. category: indolines-derivatives

4,7-Dichloroisotin (30.05 g, 139.1 mmol, 1.0 equiv, Alfa Aesar lot 10173559) and MeOH (450 mL, 15 vol) were charged to a 2-L, three-neck, round-bottom flask equipped with nitrogen line, overhead mechanical stirrer, and a temperature probe. Diethylamine (3.25 g, 0.32 equiv, Sigma- Aldrich lot SHBD5313V) was added over 3 min (the slurry becomes dark red). A very slight increase in temperature (from 17.5 C to 18.8 C) was observed. 1- [4-(Dimethylamino)phenyl]ethanone 2 (44.3 g, 1.95 equiv, ArkPharm lot 0000197- 130717000) was then added via a plastic funnel and the funnel was rinsed with MeOH (75 mL, 2.5 vol). A decrease in the reaction temperature to 15.1 C was observed. Upon stirring for a few minutes, a dark red solution with a few undissolved particles was obtained. The solution was stirred at ambient temperature and periodically sampled for in-process control (IPC) by HPLC. After 23 h of reaction, additional diethylamine was added via syringe (1.42 g, 0.14 equiv) and the stirring continued at ambient temperature. After 40.5 h, a light slurry formed. Solid 2 was added in portions (54.1 g, 2.38 equiv, ArkPharm lot 0000197- 130717000 and 3.2 g, 0.14 equiv, TCI lot GK01-BRAH) for a total of 4.47 equiv of acetophenone 2. After 88 h of reaction, IPC by HPLC showed less than 1% AUC of isatin 1 present in the reaction mixture. A heavy precipitate had formed. After 4.5 days, the reaction mixture was concentrated under reduced pressure (water bath <40 C), then under high vacuum to afford approximately 84 g of a solid mixture, lot BIO-W-22-11. The solid was dissolved in a mixture of dichloromethane (385 mL) and MeOH (140 mL) and adsorbed over 100 g of silica gel. The solvent was removed under reduced pressure and the dry product/silica mixture was loaded onto a column containing silica gel (1 kg, pre-packed with heptanes) for a flash chromatographic purification. Elution was started with 10% ethyl acetate in heptanes and a gradient up to 100% ethyl acetate was applied, and then switched to 10% methanol in ethyl acetate. Fractions of 500 mL and up to 2 L were collected. The product containing fractions, where product had started to precipitate, were combined and concentrated down to approximately 1 L. The resulting precipitate was filtered out, reslurried in EtOAc/MeOH (75:25 ratio, 200 mL), filtered, and washed with MeOH to afford a first crop of compound. The first filtrate was concentrated to a low volume, added MeOH to precipitate a second crop of compound. Filtrates from isolation of both crops were combined, concentrated to a low volume, taken up in 25 mL of MeOH, and the resulting solid was filtered to afford a third crop of compound. All three crops were dried under high vacuum at ambient temperature for a day and at 40 C for four days. The total combined weight was 40.03 g, corresponding to 76% yield of compound (uncorrected by purity or solvent content). Solid is off-white (with a very pale yellow to peach shade. The synthetic route of 4,7-Dichloroindoline-2,3-dione has been constantly updated, and we look forward to future research findings. Reference:
Patent; TOKALAS, INC.; VERNIER, Jean-michael; (82 pag.)WO2016/57698; (2016); A1;,
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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. 446292-08-6, name is (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Recommanded Product: 446292-08-6

2-({(5S) -2-oxo-3-[4- (3-oxo-4-morpholinyl) phenyl] -1,3-oxazolidin-5- yl} methyl)-1,3(2H) -dione (Formula 5) were added 75 ml of ethanol and 8.1 ml of a methylamine solution (concentration in water 40%) was added.The reaction mixture was then diluted with 60In Heating, Stir at this temperature for 2 hours.Confirm that the reaction is completed, and while maintaining the temperature, dilute the solution with 50 ml of ethanol and 3.04 ml of phosphoric acid, and slowly add the solution to the reaction solution. After confirming that the crystallization of the product was initiated and cooling to 20 C, the precipitated reaction product was filtered under suction. The resulting solid was dispersed in 110 ml of methanol, refluxed for 30 minutes and stirred, and then cooled to room temperature. The resulting crystals were filtered,And dried at 50 DEG C for 4 hours to obtain 11.1 g of morpholine diphosphate (Formula 2). (Yield: 96.0%)

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; IL DONG PHARMACEUTICAL CO., LTD.; LEE, Ki Yong; KWON, Jae Wook; SEO, Myeong Won; KANG, Jae Hoon; (15 pag.)KR2017/98031; (2017); A;,
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Application of 20780-72-7, These common heterocyclic compound, 20780-72-7, name is 4-Bromoisatin, 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.

Take 4-bromo indolone 1.0g (4.4mmol) into a 25mL round bottom flask,4 mL of N, N-dimethylformamide was added,Stirring to make it fully dissolved, and then adding 1.83 g (13.2 mmol) of anhydrous potassium carbonate,Further, 1.0 g (6.6 mmol) of methyl iodide was added.The reaction at room temperature for 8h, TLC detection of raw materials disappeared, adding 30mL of water,Then, the mixture was extracted with ethyl acetate (100 mL × 3), the combined organic phases were dried over anhydrous sodium sulfate,The solvent was decanted and the residue purified by petroleum ether: ethyl acetate = 10: 1200-300 mesh silica gel column.There was obtained 0.90 g of 1-methyl-4-bromoindodione in 85percent yield.

Statistics shows that 4-Bromoisatin is playing an increasingly important role. we look forward to future research findings about 20780-72-7.

Reference:
Patent; Tianjin Kunjian Bio-pharmaceutical Co., Ltd.; Yu Peng; Han Kailin; Mao Huihua; Qiu Dongxu; (12 pag.)CN104402794; (2017); B;,
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Related Products of 100510-65-4, 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. 100510-65-4, name is 6-Amino-3,3-dimethylindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

a) 25 g. (0.142 mol) 6-Amino-1,3-dihydro-3,3-dimethyl-(2H)-indolin-2-one in 250 ml. 2N hydrochloric acid were mixed, while cooling with ice, within the course of 15 minutes with a solution of 10.3 g. (0.15 mol) sodium nitrite in 20 ml. water and, after the addition, stirred for 15 minutes. After mixing with 2.13 g. (0.036 mol) urea, the clear solution, after stirring for a further 10 minutes, was added dropwise to a solution, warmed to 50 C., of 24.4 g. (0.5 mol) sodium cyanide, 15.2 g. (0.17 mol) cuprous cyanide and 22.6 g. (0.21 mol) sodium carbonate in 820 ml. water and heated for 5 minutes to 90 C. After cooling, the precipitate was filtered off with suction, washed with water and, after drying, recrystallized from ethanol. There were obtained 15 g. (57% of theory) 2,3-dihydro-3,3-dimethyl-2-oxo-(1H)-indole-6-carbonitrile in the form of colourless crystals; m.p. 243-246 C.

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-Amino-3,3-dimethylindolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Boehringer Mannheim GmbH; US5019587; (1991); A;,
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These common heterocyclic compound, 1029691-06-2, name is 2-(3-Oxocyclopentyl)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. COA of Formula: C13H11NO3

Mix (±)-2-(3-oxo-cyclopentyl)-isoindole- 1 ,3-di- one (12.7 g, 55.3 mmol) and 4-cyanophenylhydrazine-HC1 (8.53 g, 50.3 mmol) in HOAc (200 mE) and 4N HC1 dioxane (50 mE). Using mechanical stirring, heat the reaction to 90 C. for 18 h, then add additional 4N HC1 dioxane (20 mE). Heat the reaction to 100 C. for 18 h. Dilute the reaction mixture with water (600 mE) and collect a black solid by vacuum filtration. Sonicate the solid with MeOH (200 mE), then collect and dry in a vacuum oven to give 10.94 g (66%) of a gray-brown solid. MS (mlz): 328 (M+H), 326 (M-H)

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

Reference:
Patent; Eli Lilly and Company; Benson, Charles Thomas; (29 pag.)US2017/172992; (2017); A1;,
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Adding a certain compound to certain chemical reactions, such as: 19155-24-9, name is 3,3-Dimethylindolin-2-one, 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 19155-24-9, Recommanded Product: 3,3-Dimethylindolin-2-one

To a suspension of dimethyl oxidole (68 g of 74 percent strength crude, 280 mmol) in DMF (51 g, 700 mmol.) and toluene (200 rriL), a toluene solution of (Me3Si)2NLi (840 ml_, 1 M, 840 mmol) was added dropwise while keeping the mixture below 100C to give a dark solution. A solution of epoxy alcohol (76 g of 85percent strength, 350 mmol) and Ti(OiPr)4 (103 g, 360 mmol) in toluene (400 ml_) was added to the above dark solution at below 100C. The reaction mixture was stirred for 20 hours at 200C before cooling to 00C. A solution of HCI (660 g, 37percent in water) in water (750 g) was added at below 200C to give a bi-phasic mixture. The two layers were separated. The organic layer was washed with NaOH (400 ml_, 0.7 N in water, 280 mmol), and brine (230 g). The organic layer was filtered through a silica gel (150 g) plug. The silica gel plug was rinsed with. EtOAc (1100 ml_). The filtrate was concentrated in vacuo at 50°C to a volume of 240 ml_. This concentrate was diluted with CH3CN (300 ml_) to give 1-[(1S,2S)-1-(3,5-difluorophenyl)-2,3-dihydroxypropyl]- 7-fluoro-3,3-dimethyl-1 ,3-dihydro-2H-indol-2-one as a CH3CN solution, 431 g of a 20.8percent strength solution, yield: 88percent.

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, 3,3-Dimethylindolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; WYETH; WO2008/24492; (2008); A2;,
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Application of 99365-40-9, 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. 99365-40-9, name is 6-Bromoindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows.

n-Butyllithium (2.25 M in hexane, 130 mL, 259.4 mmol) was added drop wise at -40C to a solution of 6-bromoindolin-2-one (25.0 g, 117.9 mmol) and diisopropylamine (36.54 mL, 259.4 mmol) in THF (500 mL).The mixture was stirred for 45 mm at that temperature, 1,2-dibromoethane (31.0 mL, 353.7 mmol) wasadded drop wise and stirring was continued for 16 h while the temperature was slowly raised to RT. Thereaction mixture was quenched with 4 N HCI (400 mL) and the aqueous part was separated andextracted with EtOAc (3x 100 mL). The combined organic layers were washed with brine and dried overNa2504. The solvents were evaporated and the residue was triturated with EtOAchexane (1:4, 200 mL),filtered and washed with EtOAc/hexane (1:4, 100 mL). Brown solid. Yield: 26.0 g (92%). HPLC (method 1): R = 2.92 mi mlz [M+H] = 240.0 (MW calc. 238.08)

The chemical industry reduces the impact on the environment during synthesis 6-Bromoindolin-2-one. I believe this compound will play a more active role in future production and life.

Reference:
Patent; GRUeNENTHAL GMBH; KONETZKI, Ingo; JAKOB, Florian; WAGENER, Markus; WELBERS, Andre; HESSLINGER, Christian; (138 pag.)WO2017/108203; (2017); A1;,
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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. 32692-19-6, name is 5-Nitroindoline, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C8H8N2O2

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.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 32692-19-6.

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;,
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Reference of 99365-40-9, 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. 99365-40-9, name is 6-Bromoindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A solution of 28 (3.74 g, 17.64 mmol) in dry THF (150mL) was degassed with N2 for 15 min. The solution was then cooled to-78 C and a solution of NaHMDS (1 M in THF, 88.2 mL) was added dropwise over a10 min period. The reaction was stirred at -78 C for 1 h before adding solid N-benzyl-2-chloro-N-(2-chloroethyl)ethan-1-amine HCl salt (5.20 g, 19.40 mmol) in oneportion. The reaction was stirred at -78 C for 1 h before removing the coldbath and allowing the reaction to warm to rt. Upon reaching rt, the reactionwas heated to 70 C (reflux) for 15 hours. The mixture was cooled to 0 C and asaturated aq. NH4Cl solution (150 mL) was added followed by EtOAc(300 mL) for the workup. The organic layer was separated and the aqueous layerwas extracted twice with EtOAc (50 mL x 2).The organic layers were combined, washed with brine, dried using Na2SO4and evaporated to afford the crude product. This crude product wastriturated using hot petroleum ether to give 29 (6.10 g, 93%) as a pink colored solid.

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

Reference:
Article; Lotesta, Stephen D.; Marcus, Andrew P.; Zheng, Yajun; Leftheris, Katerina; Noto, Paul B.; Meng, Shi; Kandpal, Geeta; Chen, Guozhou; Zhou, Jing; McKeever, Brian; Bukhtiyarov, Yuri; Zhao, Yi; Lala, Deepak S.; Singh, Suresh B.; McGeehan, Gerard M.; Bioorganic and Medicinal Chemistry; vol. 24; 6; (2016); p. 1384 – 1391;,
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