Month: January 2021

Related Products of 6326-79-0, These common heterocyclic compound, 6326-79-0, name is 6-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.

The conversion of the substituted isatins to the corresponding indazole-3-carboxylic acids is essentially the same method as described for indazole-3-carboxylic acid: Snyder, H. R., et. al. J. Am. Chem. Soc. 1952, 74, 2009. The substituted isatin (22.1 mmol) was diluted with 1 N sodium hydroxide (24 mL) and was heated at 50 C. for 30 min. The burgundy solution was allowed to cool to rt and was maintained for 1 h. The reaction mixture was cooled to 0 C. and was treated with a 0 C. solution of sodium nitrite (22.0 mmol) in water (5.5 mL). This solution was added through a pipet submerged below the surface of a vigorously stirred solution of sulfuric acid (2.3 mL) in water (45 mL) at 0 C. The addition took 15 min and the reaction was maintained for an additional 30 min. A cold (0 C.) solution of tin (II) chloride dihydrate (52.7 mmol) in concentrated hydrochloric acid (20 mL) was added to the reaction mixture over 10 min and the reaction mixture was maintained for 60 min. The precipitated solids were isolated by filtration, washed with water, and dried to give a quantitative mass balance. This material was of sufficient purity (1H NMR and LC/MS) to use in the next step without further purification. Alternatively, the acid was recrystallized from acetic acid to provide pure material. The following acids were prepared using this method: 6-Bromo-1H-indazole-3-acid. 5-Methoxy-1H-indazole-3-acid. 6-Methoxy-1H-indazole-3-acid.

The synthetic route of 6326-79-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Schumacher, Richard; Danca, Mihaela Diana; Ma, Jianguo; Herbert, Brian; Nguyen, True Minh; Xie, Wenge; Tehim, Ashok; US2007/78147; (2007); A1;,
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Adding a certain compound to certain chemical reactions, such as: 13220-46-7, name is 4-Methylindolin-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 13220-46-7, Product Details of 13220-46-7

4-Methyl-2-oxindole (5 g) in 40 mL of acetonitrile was treated with 7.26 g of N-bromosuccinimide and stirred at room temperature for 4 hours. Thin layer chromatography (ethyl acetate:hexane 1:2, silica gel) showed a mixture of 5-bromo (Rf 0.3) and 5,7-dibromo (Rf 0.5) products. Another 7,26 g of N-bromosuccinimide was added and the mixture stirred for 4 additional hours. The solid was collected by vacuum filtration, washed with 20 mL of acetonitrile and dried to give a 1:1 mixture of mono and dibromo compounds. The filtrate was concentrated and chromatographed on silica gel (ethyl acetate:hexane (1:2)) to give 1.67 g of 5-bromo-4-methyl-2-oxindole as a beige solid. The remaining 1:1 mixture of solids was recrystallized twice from glacial acetic acid to give 3.2 g of 5,7-dibromo-4-methyl-2-oxindole as a light orange solid. The filtrates from this material were chromatographed as above to give 0.6 g of 5-bromo-4-methyl-2-oxindole and 0.5 g of 5,7-dibromo-4-methyl-2-oxindole

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:
Patent; Sugen, Inc.; US6878733; (2005); B1;,
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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. 6872-06-6, name is 2-Methylindoline, A new synthetic method of this compound is introduced below., Computed Properties of C9H11N

Example 1Synthesis of 5-((2,3-dihydrobenzo[b][1,4]dioxin-6-yl)sulfonyl)-2-methyl-1-(methylsulfonyl)indolineReagents MW Mole Reagent/raw material (g/mole) Quantity moles ratio 2-methylindoline 161.20 1 g 7.5 mmol 1 eq. methanesulfonyl chloride 114.55 1.04 g 9.0 mmol 1.5 eq. 2-methyl-1-(methyl- 239.29 276 mg 1.3 mmol 1.2 eq. sulfonyl)indoline 2,3-dihydro- 375.93 250 mg 1.06 mmol 1.0 eq. benzo[b][1,4]dioxine- 6-sulfonyl chloride Aluminium chloride 133.3 170 mg 1.3 mmol 1.2 eq. Step I: 2-methylindoline was dissolved in 5 mL dry pyridine, and methanesulfonyl chloride was dropped in 2 portions under N2. The reaction was stirred for 2 hours at room temperature and an intense red color developed. When the reaction was complete as determined by HPLC (product Rt=8.51 min, st. material Rt=4.18 min) using the H2O-Acetonitrile (CAN) gradient given below with a Gemini-NS C18, 3 mum, 100 , 150¡Á4.6 mm column chromatography as well as by TLC (8/2 PE/EtOAC), the crude reaction was poured into 100 mL cold 0.5M HCl, and extracted twice with 50 mL CH2Cl2. The organic phase was evaporated, and the evaporation residue was purified by passing through a silica plug (100 g silica gel in large sinter glass). The product eluted in 7/3 PE/EtOAC, while all of the pink polar byproduct was retained on silica. The organic phase was dried on Na2SO4, and then evaporated and used for the next step without further purification (Product 100% pure, 455 mg, yield 30%).HPLC Purification Protocol Time (min) FlowH2O (%) ACN (%) 1 100 0 0.02 1 100 0 11.0 1 0 100 13.0 1 100 0 18.0 1 100 0 18.1 0.2 100 0

The synthetic route of 6872-06-6 has been constantly updated, and we look forward to future research findings.

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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Electric Literature of 6326-79-0, These common heterocyclic compound, 6326-79-0, name is 6-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.

Step 2 Compound 1251 B (1.219g, 5.32 mmol) was dissolved in CCI4 (30 mL). NBS (947 mg, 5.32 mmol) and benzoyl peroxide (66 mg, 0.27 mmol) was added. The solution was stirred at 850C for 2 hours. After cooling down, the solid was filtered and the organic layer was washed with water (10 mL). The organic layer was dried over Na2SO4, concentrated by rotary evaporator, dried under vacuum. The residue was then dissolved in NH3-MeOH (7N, 10 mL) and transferred into a 75 mL pressure bottle. The solution was stirred at 90 0C for over night. The product was purified by C18 chromatography (CH3CN/water: 5% to 90%, with addition of 0.1% HCO2H) to give compound 1251C (800mg, 71%).

Statistics shows that 6-Bromoisatin is playing an increasingly important role. we look forward to future research findings about 6326-79-0.

Reference:
Patent; SCHERING CORPORATION; WO2007/84451; (2007); A1;,
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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 61-70-1 as follows. SDS of cas: 61-70-1

Example Xl; 1 -methyl-5-nitro-1 ,3-dihvdro-indol-2-one2 g 1 -methyl-1 ,3-dihydro-indol-2-one are dissolved in 10 ml concentrated sulphuric acid and cooled to 00C . To this is added dropwise a solution of 620 mul concentrated nitric acid in 2 ml concentrated sulphuric acid and the mixture is stirred for 30 minutes. Then it is poured onto 50 g ice, stirred for 1 hour, the solid is removed by suction filtering and dried in vacuo. Yield: 1.7 g (65 % of theory) Mass spectrum (ESI+): m/z = 193 [M+H]+

According to the analysis of related databases, 61-70-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; WO2009/16119; (2009); A1;,
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Some common heterocyclic compound, 875003-43-3, name is 7-Fluoro-1-methylindoline-2,3-dione, molecular formula is C9H6FNO2, 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. Safety of 7-Fluoro-1-methylindoline-2,3-dione

To a 1-L three neck round bottom flask equipped with a mechanical overhead agitator, a thermocouple, and an ice-water bath was charged NaOH (5.0 N) in water (140.0 mL, 700 mmol, 5.0 mol/L) followed by deionized water (140.0 mL, 7771 mmol, 100 mass%) to form a colorless transparent solution (T = 20.2 C). 7-fluoro-l- methylindoline-2,3-dione (R, 25 g, 139.55 mmol, 100 mass%) was charged portion-wise while controlling the batch temperature at less than 24 C with an ice-water bath to provide cooling. 7-fluoro-l-methylindoline-2,3-dione was charged and 50 mL of water was used to rinse off the charging funnel, the spatula, and the charging port. The reaction mixture was a thick yellow-green hazy suspension. The yellow-greenish suspension was cooled to 5.0 C with an ice-water bath. The mixture was stirred for 15 min. Next, hydrogen peroxide (50% wt.) in water (11.0 mL, 179 mmol, 50 mass%) was charged to a 60 mL additional funnel with deionized (4.0 mL, 220 mmol, 100 mass%). The concentration of H2O2 post dilution was ~ 36.7%. The dilute hydrogen peroxide solution was added over a period of 11 minutes to the 1 L round bottom flask cooled with an ice- water bath and stirred at 350 rpm. The reaction mixture color was observed to become lighter in color and less viscous after 5 mL of the peroxide solution was added. After adding 10 mL of peroxide solution, the reaction mixture became clear with visible solids. At the end of addition, the reaction mixture was a green-tea colored transparent solution. The ice-water bath was removed (batch temperature was 16.6 C), and the transparent, greenish yellow reaction mixture was allowed to warm to ambient temperature (21.0 C), stirred for 1 hr. After the reaction was complete, (1.0 hr), the reaction mixture was cooled to 4.3 C with an ice-water bath. The reaction mixture was neutralized by the addition 6.0 N HCl (aq.) over a period of 3 hours to minimize foaming and the exotherm, resulting in the formation of a yellow-green suspension. The ice-bath was removed and the quenched reaction mixture was stirred at ambient temperature for 20 min. The yellow-green colored reaction mixture was transferred to a 2 L separatory funnel. Dichloromethane (300.0 mL, 4680 mmol, 100 mass%) was charged to the separatory funnel via rinsing the 1 L 3-necked round bottom flask. The separatory funnel was shaken vigorously, then allowed to settle (phase split was fast). Gas evolution was minor. The top aqueous layer was dark amber in color. The bottom dichloromethane layer was tea-green in color. The bottom rich dichloromethane layer was transferred to a clean 1 L Erlenmeyer flask. Next, the 1 L three necked round bottom flask was rinsed again with dichloromethane (200.0 mL, 3120 mmol, 100 mass%). The dichloromethane rinse was added to the separatory funnel. The separatory funnel was shaken vigorously and allowed to settle (phase split was fast). The top aqueous layer was amber in color (lighter); the bottom dichloromethane layer was lighter green. The bottom rich dichloromethane layer was transferred to the 1 L Erlenmeyer flask. Dichloromethane (200.0 mL, 3120 mmol, 100 mass%) was charged to the separatory funnel and the separatory funnel was shaken vigorously. The contents were allowed to settle (phase split was fast). The bottom rich dichloromethane layer was transferred to the same 1 L Erlenmeyer flask. Peroxide test strip showed > 10 mg/Liter peroxide concentration. The total volume of the aqueous layer was 540 mL. In a separate 250-mL Erlenmeyer flask was added sodium thiosulfate pentahydrate (20.0 g, 80.6 mmol, 100 mass%) followed by deionized water (180.0 mL, 9992 mmol, 100 mass%) to form a colorless solution (10% wt. solution). The sodium thiosulfate solution was added to the combined dichloromethane rich solution in the 1 L Erlenmeyer flask. The contents of the flask were stirred vigorously for 10 hrs at ambient temperature. Peroxide strip did not detect the presence of peroxides in the bottom DCM layer. The top Na2S203 layer was amber in color, the bottom dichloromethane layer was much lighter in color, but was still amber in color. After 10 hrs, the mixture was transferred to a 1 L separatory funnel. The top aqueous layer was discarded. The dichloromethane solution was washed with 150.0 mL of saturated brine solution. After phase split, the bottom rich dichloromethane layer was transferred to a 1 L flask. The dichloromethane solution was distilled to approximately 150 mL to obtain an amber-colored solution. Next, dichloromethane (120 mL, 1872 mmol, 100 mass%) was added and the mixture was heated to 35-40 C to fully dissolve the solids. The amber solution was filtered through a 0.45 micron PTFE membrane Zap Cap filtration unit into a 1 L flask. The filtrate was transferred into a 3-neck 1 L round bottom flask fitted with a thermocouple, a heating mantle, a mechanical agitator, and a condenser with a nitrogen inlet. To the flask was charged dichloromethane (120 mL, 1872 mmol, 100 mass%) via r…

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 875003-43-3, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; CARRASQUILLO, Ronald; GENG, Peng; HUANG, Eric C.; KATIPALLY, Kishta; LEE, Andrew; MUDRYK, Boguslaw; QIAN, Xinhua; RAZLER, Thomas M.; WANG, Jianji; WEI, Carolyn S.; WISNIEWSKI, Steven R.; ZHU, Ye; (79 pag.)WO2018/118830; (2018); 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. 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, A new synthetic method of this compound is introduced below., name: 5-(Trifluoromethoxy)indoline-2,3-dione

General procedure: The mixture of isatin 1 (58.9 mg, 0.4 mmol), antipyrine 2 (37.6 mg, 0.2 mmol) andimidazole (20 mol %, 0.04 mmol) in 1 mL H2O were stirred at 80 . Once thereaction completed, the solid mixture was filtered, washed by water and dried undervacuum to afford the analytically pure products 3. In some cases, the desired pureproducts were obtained by silica gel chromatography using ethyl acetate as eluent.

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, Yong; Nie, Long-Jun; Luo, Liang; Mao, Jia-Xin; Liu, Jin-Xiang; Xu, Guo-Hai; Chen, Deliang; Luo, Hai-Qing; Tetrahedron; vol. 76; 7; (2020);,
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Related Products of 16800-68-3, 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.

General procedure: 1a (35.0 mg, 0.2 mmol, 1 equiv.), tert-BuOK (22.4 mg, 0.2 mmol, 1.0 equiv.) were added to a Schlenk tube. Then 2 ml THF was added using a syringe. The reaction mixture was stirred 15min,and then added iodonium salt 2 (0.2 mmol, 1.0 eq). The reaction was stirred at 30C for 10 hours.After cooling to room temperature, the solvent was removed in vacuo and the residue was purifiedby silica gel using a proper eluent (EtOAc/Hexane) to afford the desired products

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

Reference:
Article; Zhang, Yanxia; Han, Jianwei; Liu, Zhen-Jiang; Synlett; vol. 26; 18; (2015); p. 2593 – 2597;,
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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. 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 2-(Bromomethyl)isoindoline-1,3-dione

Example 14: 6-((R)-5-{2-[((R5)-8-methoxy-l,2-dihydro-3-oxa-5,9-diaza- cyclopenta[fl]naphthalen-l-ylmethyl)-amino]-ethyl}-2-oxo-oxazolidin-3-yl)- 4H-benzo [ 1 ,4] thiazin-3-one:; 14.L rac-3-( 1 ,3-dioxo- 1 ,3-dihydro-isoindol-2-yl)-2-(3-fluoro-6-methoxy- [ 1 ,5] naphthyridin-4-yl)-propionic acid ethyl ester:; A solution of (3-fluoro-6-methoxy-[l,5]naphthyridin-4-yl)-acetic acid ethyl ester (6.78 g; prepared in analogy to the corresponding methyl ester described in WO 2007/122258) in TEtaF (30 niL) was added dropwise at -78C to a solution of LiEtaMDS (31 mL; IM in TEtaF) diluted in TEtaF (2O mL). After stirring for I h at -78C a solution of Lambda/-(bromomethyl)phthalimide (7.40 g) in TEtaF (30 mL) was added dropwise and the mixture was stirred for an additional 1 h at -78C and then overnight at rt. The yellow solution was quenched with N HCl (280 mL) and extracted with DCM. The combined org. layers were washed with H2O, dried over MgSO4, concentrated and purified by CC (Hept/EA 1 : 1), affording a light yellow foam (5.49 g; 51% yield). MS (ESI, m/z): 424.2 [M+H+].

The synthetic route of 5332-26-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; HUBSCHWERLEN, Christian; RUEEDI, Georg; SURIVET, Jean-Philippe; ZUMBRUNN ACKLIN, Cornelia; WO2010/15985; (2010); 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. 675109-26-9, name is 6-Bromoisoindolin-1-one, A new synthetic method of this compound is introduced below., Recommanded Product: 6-Bromoisoindolin-1-one

To a mixture of 6-bromo-2,3-dihydro-isoindol-1-one (10.0 g), DMAP (11.5 g) and THE (100 mL), (Boc)20 (15.4 g) was added and the mixture was stirred at room temperature for 12 hours. The resulting yellow mixture was partitioned between water and ethyl acetate, and the phases were separated. The organic phase was washed with brine anddried over Na2504. After filtration and evaporation of the solvent, the resulting residue was purified by column chromatography (silica gel, PE/EA = 15:1)to provide the subtitle compound. MS ESl: mlz = 256 [Mi-H-tBu].

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; SANOFI; SCHWINK, Lothar; BUNING, Christian; GLOMBIK, Heiner; GOSSEL, Matthias; KADEREIT, Dieter; HALLAND, Nis; LOHMANN, Matthias; POeVERLEIN, Christoph; RITTER, Kurt; WO2015/150565; (2015); A1;,
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