Tag: M.W=100-200

Reference 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.

After standing overnight the filtrate yielded 2 g of 5-carboxy-2-oxindole as a yellow solid. The crude dark brown product was dissolved in hot methanol, the insoluble material removed by filtration and the filtrate concentrated to give 5.6 g of 5-carboxy-2-oxindole as a brown solid. The combined yield was 97%. 1H-NMR (360 MHz, DMSO-d6) delta 12.56 (s, br, 1 H, COOH-5), 10.70 (s, 1 H, NH-1), 7.82 (dd, J=1.57, 7.79 Hz, 1 H, H-6), 7.74 (s, br, 1 H, H-4), 6.87 (d, J=7.79 Hz, 1 H, H-7), and 3.53 (s, 2 H, CH2-3). MS m/z (relative intensity, %) 178 ([M+1]+, 100).

The synthetic route of 102359-00-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sugen, Inc.; US6395734; (2002); B1;,
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Related Products of 19155-24-9, 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 19155-24-9 as follows.

5-bromo-1,3-dihydro-3,3-dimethyl-2H-indol-2-one 3,3-dimethyl-indol-2-one (0.65 g, 4.03 mmol) and sodium acetate (0.33 g, 4.07 mmol) were stirred in acetic acid (5 cm3) then bromine (0.66 g, 4.13 mmol) in acetic acid (5 cm3) was added drop-wise to the reaction mixture. The reaction was stirred for 50 min., and then poured into water. The mixture was basified with sodium carbonate and then extracted with ethyl acetate (*3), dried (MgSO4), filtered, and evaporated to the title compound (0.89 g, 92percent) 1H NMR (DMSO-d6) delta1.21 (s, 6H), 6.76 (d, 1H, J=8.22 Hz), 7.29 (dd, 1H, J=2.12 Hz, 8.23 Hz), 7.49 (d, 1H, J=2.03 Hz), 10.4 (s, 1H).

According to the analysis of related databases, 19155-24-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; American Home Products Corporation; Ligand Pharmaceuticals, Inc.; US6391907; (2002); B1;,
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Synthetic Route of 84575-27-9,Some common heterocyclic compound, 84575-27-9, name is 7-Methoxyindoline-2,3-dione, molecular formula is C9H7NO3, 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.

To a suspension of 7-methoxyindoline-2,3-dione (1 g, 5.6 mmol) in AcOH (5.6 mL) was added bromine (0.35 mL, 6.7 mmol) at 0 C. The mixture was allowed to stir at ambient temperature for 2 hours and then poured into ice and stirred for 30 minutes. The resulting mixture was filtered and the solids were washed with H2O to afford the title compound as an orange solid (1.3 g, 92%). MS (ESI): mass calcd. for C9H6BrNO3, 256.0; m/z found, 257.6 [M+H]+. 1H NMR (400 MHz, DMSO-d6) delta 11.22 (s, 1H), 7.48 (d, J=1.7 Hz, 1H), 7.25 (dd, J=1.8, 0.7 Hz, 1H), 3.90 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7-Methoxyindoline-2,3-dione, its application will become more common.

Reference:
Patent; Janssen Pharmaceutica NV; Ameriks, Michael K.; Laforteza, Brian Ngo; Lebold, Terry Patrick; Ravula, Suchitra; Savall, Brad M.; Shireman, Brock T.; (70 pag.)US2018/111942; (2018); A1;,
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Application of 17564-64-6, 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. 17564-64-6 name is 2-(Chloromethyl)isoindoline-1,3-dione, 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.

General procedure: The initial carbonyl compound (50 mmol) was dissolved/suspended in ethanol (50 mL) and magnetically stirred with thiosemicarbazide (50 mmol) and catalytic amounts of acetic acid for 8-24 h at room temperature. The obtained thiosemicarbazone was filtered, washed with appropriate solvent (n-hexane, petroleumether or diethyl ether) and dried under vacuum. The intermediate thiosemicarbazone (50 mmol) reacted with ethyl bromoacetate (50 mmol), in methanol (50 mL) and sodium acetate (50 mmol) at room temperature under magnetic stirring for 24 h. The resulting 4-thiazolidinone was poured on ice, filtered or extracted with chloroform (3 x 100 mL) and purified by column chromatography (SiO2, ethyl acetate/n-hexane). Then, the obtained thiazolidinone (50 mmol) was dissolved/suspended in 50 mL of anhydrous acetone in the presence of anhydrous potassium carbonate (50 mmol), and reacted with equimolar amounts of 4-nitrobenzyl bromide, 1-(chloromethyl)naphthalene and N-(chloromethyl)phthalimide for 24-48 h. The product was poured on ice, filtered or extracted with chloroform (3 x 50 mL) and purified by column chromatography (SiO2, ethyl acetate/n-hexane) in order to obtain the title compoundsin high yields. 7.1.63 2-((2-(2-(2-Methylcyclopentylidene)hydrazono)-4-oxothiazolidin-3-yl)methyl)isoindoline-1,3-dione (11C) White powder, mp 158-162 C, 83% yield; 1H NMR (400 MHz, CDCl3): delta 1.14-1.17 (d, J = 10 Hz, 3H, CH3), 1.28-1.31 (m, 2H, cyclopentane), 1.83 (bs, 1H, cyclopentane), 1.98-2.02 (m, 1H, cyclopentane), 2.25-2.30 (m, 1H, cyclopentane), 2.48-2.54 (m, 2H, cyclopentane), 3.83 (s, 2H, CH2, thiazolidinone), 5.71 (s, 2H, ArCH2), 7.76-7.77 (m, 2H, Ar), 7.86-7.88 (m, 2H, Ar). 13C NMR (100 MHz, CDCl3): delta 16.9, 22.5, 30.3, 32.5, 33.7, 39.6, 45.1, 123.6, 131.7, 134.3, 157.9, 166.7, 171.0, 182.3.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(Chloromethyl)isoindoline-1,3-dione, and friends who are interested can also refer to it.

Reference:
Article; De Monte, Celeste; Carradori, Simone; Bizzarri, Bruna; Bolasco, Adriana; Caprara, Federica; Mollica, Adriano; Rivanera, Daniela; Mari, Emanuela; Zicari, Alessandra; Akdemir, Atilla; Secci, Daniela; European Journal of Medicinal Chemistry; vol. 107; (2016); p. 82 – 96;,
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Some common heterocyclic compound, 32372-82-0, name is Isoindoline hydrochloride, molecular formula is C8H10ClN, 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. Recommanded Product: 32372-82-0

a. 2-chloro-4-(2,3-dihydro-1H-isoindol-2-yl)-pyrimidine A mixture of 0.5 g (3.35 mmol) of 2,4-dichloro-pyrimidine, 0.5 g (3.2 mmol) of 2,3-dihydro-1H-isoindol-hydrochloride and 0.6 ml (3.4 mmol) of N-ethyl-diisopropylamine is stirred in 40 ml dichloromethane for 3 hours. Then the mixture is concentrated by evaporation, the residue is distributed in ethyl acetate/water, the organic phase is separated off and concentrated by evaporation. Yield: 0.4 g (55% of theory), Rf value: 0.4 (silica gel; dichloromethane/ethanol=19:1)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 32372-82-0, its application will become more common.

Reference:
Patent; Boehringer Ingelheim Pharma KG; US2003/55263; (2003); 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. 480-91-1, name is Isoindolin-1-one, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: Isoindolin-1-one

General procedure: Isoindolin-1-one (200 mg, 1.50mmol) was dissolved in super-dry DMSO (4 mL), and Cs2CO3 (1215 mg, 3.75 mmol), CuI (58 mg, 0.30mmol) and N1,N2-dimethylethane-1,2-diamine (27 mg, 33 muL, 0.30 mmol) were added to the solution.The resulting mixture was stirred at room temperature for 10 min, after which iodobenzene (2.25mmol) was added. Then the mixture was heated to 120 C. When TLC showed that isoindolin-1-onehad been fully converted, the reaction was stopped. The mixture was extracted with ethyl acetate (20mL) and H2O (10 mL). The water phase was re-extracted with ethyl acetate (20 mL). The organic layerwas combined and washed with brine (10 mL). Then the solution was dried over anhydrous MgSO4,filtered and concentrated, and the crude residue was purified by flash chromatography over silica gelusing CH2Cl2/CH3OH as the gradient elution to afford the title compounds.

According to the analysis of related databases, 480-91-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wang, Yixuan; Wang, Huiqiang; Jiang, Xinbei; Jiang, Zhi; Guo, Tingting; Ji, Xingyue; Li, Yanping; Li, Yuhuan; Li, Zhuorong; Molecules; vol. 24; 5; (2019);,
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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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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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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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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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