Author: Jessica.F

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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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. 104618-32-8, name is 2-(4-Oxocyclohexyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 2-(4-Oxocyclohexyl)isoindoline-1,3-dione

Example 11 3-Amino-6-(N-methylsulphonamidomethyl)-1,2,3,4-tetrahydrocarbazole oxalate Reaction of 4-phthalimidocyclohexanone (0.42 g) with 4-(N-methylsulphonamidomethyl) phenyl hydrazine hydrochloride (0.44 g), and subsequent deprotection by the method described in example 3, gave the title compound free base. This was treated with oxalic acid to give the oxalate salt (0.15 g), mp 218-222C dec.

According to the analysis of related databases, 104618-32-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SMITHKLINE BEECHAM PLC; EP603432; (1994); A1;,
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Application of 118289-55-7, These common heterocyclic compound, 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)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.

88.7 g (0.837 mols, 3.21 molar equivalents) of sodium carbonate, 600 ml of acetonitrile and 66.7 g (0.261 mols, 1.0 molar equivalent) of 3- (1-piperazinyl) -1, 2- benzisothiazole hydrochloride [hydrochloride of the compound of formula (III) ] are added into a beaker –> equipped with a magnetic stirrer. The resulting white suspension is stirred for 10 minutes. At this point 60.0 g (0.261 mols, 1.0 molar equivalent) of 5- (2- chloroethyl) -6-chloro-l, 3-dihydro-indole-2- (2H) -one [compound of formula (II) wherein X is chlorine] and 0.3 g (0.002 mols, 0.008 molar equivalents) of NaI are added. The resulting brown suspension is charged into a 1 L reactor vessel, which is purged with nitrogen and heated to 120-125 C (internal pressure increases to 400-500 kPa) for 25 hours. The reaction is cooled to room temperature, stirred for 30 minutes, filtered and the solid washed with acetonitrile. A wet mixture of zipradisone and inorganic salts is obtained.The resulting wet mixture is stirred with 675 ml of water at reflux temperature for 1 h to remove inorganic salts . The suspension is cooled at room temperature, stirred for 30 minutes and filtered. The solid is washed with water, and 140 g of wet solid (corresponding to 87 g of dry material) are obtained.The wet solid is stirred again with water at reflux temperature for 1 h to remove residual inorganic salts. The suspension is cooled to room temperature, stirred for 30 minutes and filtered. The solid is washed with water, and 170 g of wet solid (corresponding to 81 g of dry- material) are obtained. HPLC analysis reveals a purity of 97.8%.To remove starting materials present in the wet solid obtained in the previous step, it is stirred twice with 400 ml of tetrahydrofuran at reflux temperature. The solution is cooled to room temperature, stirred for 30 –> minutes and filtered. The solid is washed twice with 40 ml of tetrahydrofuran at room temperature and 60 g of wet solid, corresponding to 54.8 g of dry material, are obtained.The solid obtained is ziprasidone base having a purity of 99.4% by HPLC and the global yield from the starting compound (II) or (III) is 51% molar. Potentiometric titration with HClO4: 100.03% Optionally, Ziprasidone base could be converted to ziprasidone hydrochloride.;Example 3. Large scale preparation of ziprasidone baseInto a 100 1 Hastelloy reactor are loaded:- 8 kg (31.3 mols 1.0 molar equivalent) of 3-(l- piperazinyl) -1, 2-benzisothiazole hydrochloride[hydrochloride of compound of formula (III) ] ,- 8.64 kg (37.5 mols, 1.2 molar equivalents) of 5- (2- chloroethyl) -6-chloro-l, 3-dihydro-indole-2- (2H) -one [compound of formula (II) wherein X is chlorine] ,- 10.6 kg (100 mols, 3.20 molar equivalents) of sodium carbonate,- 0.038 kg (0.25 mols, 0.008 molar equivalents) of NaIThe reactor is closed and blanketed with vacuum/nitrogen. Then, 56.3 kg of acetonitrile are loaded and the mixture is stirred for 10 minutes. The reactor is heated to reflux (80-82 C) . Then the reactor is closed and –> continued to be heated up to 120-125 C (internal pressure increases to 300 kPa) . The reaction mixture is kept under these conditions for 25 hours. Then the content is cooled down to room temperature and the solid is centrifuged and washed with 2 x 12 kg of acetonitrile. A wet solid containing ziprasidone base and inorganic salts is obtained.The resulting solid is loaded in a 100 1 Hastelloy reactor. The reactor is blanketed and 52 kg of water are loaded. The suspension is stirred at reflux conditions(80-850C; due to the presence of acetonitrile) for 1 h to remove inorganic salts. The suspension is cooled down to room temperature, stirred for 30 minutes and the solid is centrifuged and washed with 2 x 9 kg of water. 17.97 kg of wet solid are obtained.The wet solid from the previous step is loaded in a 100 1 Hastelloy reactor. The reactor is blanketed and 57 kg of tetrahydrofuran are loaded. The suspension is stirred at reflux conditions for 1 h. The suspension is cooled down to room temperature, stirred for 30 minutes and the solid is filtered through a Nutsche Filter and washed with 2 x 16 kg of tetrahydrofuran. 10.53 kg of wet solid (corresponding to 8.57 kg of dry material) are obtained.The solid obtained is ziprasidone base having a purity by HPLC of 99.2%. The global yield from the starting compound (III) is 66.3% (molar yield) . Optionally, Ziprasidone base could be converted to ziprasidone hydrochloride.Example 4 : Preparation of ziprasidone base –> 13.26 g (0.400 mols, 3.20 molar equivalents) of sodium carbonate, 10.00 g (0.039 mols, 1.0 molar equivalent) of3- (1-piperazinyl) -1, 2-benzisothiazole hydrochloride [hydrochloride of the compound of formula (III)], 10.80 g(0.0469 mols, 1.2 molar equivalent) of 5- (2-chloroethyl) -6-chloro-l, 3-dihydro-indole-2- (2H) -one [compound of formula (II) wherein X is chlorine] and 7.030 g (0.0469 mols, 1.2 molar equivalents) of NaI are added into a 250 ml round bottom, three necked reaction vessel, equi…

The synthetic route of 118289-55-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEDICHEM, S.A.; WO2006/34964; (2006); A1;,
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Related Products of 150544-04-0, A common heterocyclic compound, 150544-04-0, name is 6-Aminoindolin-2-one, molecular formula is C8H8N2O, 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 above compound (2 g) and ethyl 1,3-dioxobenzo[c]azolidine-2-carboxylate (1.1 eq) in THF was refluxed overnight. The reaction was cooled and the precipitate was filtered. The gray solid (2 g) was heated with acetic anhydride (2 eq) in acetic acid (40 ml) at 115° C. overnight. The solvent was evaporated and the product was triturated with 50percent EtOAc/Hexane and filtered to give 1-acetyl-6-(1,3-dioxobenzo[c]-azolidin-2-yl)-2-oxoindoline as a dark gray solid.

The synthetic route of 150544-04-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chen, Guoqing P.; US2004/259916; (2004); A1;,
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