Tag: M.W=200-300

Electric Literature of 954-81-4,Some common heterocyclic compound, 954-81-4, name is N-(5-Bromopentyl)phthalimide, molecular formula is C13H14BrNO2, 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 4-[5-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-pentyloxy]-benzoic acid methyl ester A mixture of 4-hydroxy-benzoic acid methyl ester (3.01 g, 19.8 mmol), 2-(5-bromo-pentyl)-isoindole-1,3-dione (3.9 g, 13.2 mmol), and K2CO3 (1.82 g, 13.2 mmol) in acetone (150 mL) was heated to reflux for 24 hrs. The reaction mixture was cooled to rt and the solvents were removed in vacuo. The crude was diluted in EtOAc and washed with 1N NaOH and brine. The organic layer was dried over sodium sulfate. The solvents were removed in vacuo. The crude was recrystallized from EtOAc to afford the title compound as a white solid (4 g, 83%). 1H-NMR (CDCl3): delta 7.95-7.98 (m, 2H), 7.83-7.86 (m, 2H), 7.70-7.73 (m, 2H), 6.86-6.89 (m, 2H), 4.00 (t, 2H, J=6.22 Hz), 3.88 (s, 3H), 3.73 (t, 2H, J=7.29 Hz), 1.82-1.89 (m, 2H), 1.73-1.81 (m, 2H), 1.50-1.57 (m, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route N-(5-Bromopentyl)phthalimide, its application will become more common.

Reference:
Patent; 3-Dimensional Pharmaceuticals, Inc.; US2004/9995; (2004); A1;,
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552330-86-6, name is 5-Bromoisoindolin-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. Recommanded Product: 552330-86-6

Step 1: tert-Butyl 5-bromo-1-oxoisoindoline-2-carboxylate (0650) (0651) (Boc)2O (69.5 g, 318.33 mmol) was added slowly to 5-bromoisoindolin-1-one (45 g, 212.22 mmol) and DMAP (38.9 g, 318.33 mmol) in acetonitrile (1000 mL) at room temperature over a period of 30 minutes under nitrogen. The resulting solution was stirred at this temperature for 12 hours. The solvent was removed under reduced pressure. The residue was treated with water (500 mL), extracted with DCM (3¡Á500 mL), the organic layer was dried over Na2SO4, filtered and evaporated to afford brown oil. The crude product was purified by flash silica chromatography, elution gradient 0 to 10% EtOAc in petroleum ether. Pure fractions were evaporated to dryness to afford tert-butyl 5-bromo-1-oxoisoindoline-2-carboxylate (55.0 g, 83%). (0652) LC/MS: m/z=256,258 [M-tBu+H]+. 1H NMR (400 MHz, CDCl3) delta 1.62 (s, 9H), 4.76 (s, 2H), 7.63-7.66 (m, 2H), 7.78 (d, J=8.0 Hz, 1H).

The synthetic route of 552330-86-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AstraZeneca AB; NARJES, Frank; OLSSON, Roine Ingemar; VON BERG, Stefan; LEVER, Sarah; (112 pag.)US2017/166527; (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. 3335-98-6, name is 1-Phenyloxindole, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 1-Phenyloxindole

General procedure: An oven-dried reflux tube equipped with a magnetic stir bar and a Teflon stopcock was charged with aryl halide (1 mmol), oxindole (1 mmol),potassium carbonate (1.1 mmol), catalyst nanoparticles (0.05 mmol)and 1,4-dioxane (2 ml) and heated at 70 C. The mixture was vigorously stirred under these reaction conditions and completion of the reaction was monitored by TLC (EtOAc: n-hexane, 25:75). After completion of the reaction, the reaction mixture was cooled to room temperature, the magnetic nanoparticles of the catalyst were collected using a magnet. Ethyl acetate (5 mL) and water (10 mL)were added to the mixture in the next step. The aqueous layer was furtherextracted by ethyl acetate (2*5 mL). The combined organic layerswere washed with saturated brine, dried over CaCl2, filtered, and concentrated to give a residue which was purified by recrystallization from ethanol and water or by column chromatography on silica gelusing EtOAc: n-hexane, 1:7.

According to the analysis of related databases, 3335-98-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Moghaddam, Firouz Matloubi; Tavakoli, Ghazal; Latifi, Fatemeh; Saeednia, Borna; Catalysis Communications; vol. 75; (2016); p. 37 – 41;,
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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 3339-73-9 as follows. Product Details of 3339-73-9

General procedure: An aqueous solution of metal (Li/Na) carbonate (4.5mmol in 50ml) was added drop wise to a well-stirred solution of NPA (9.1mmol) in ethanol (40ml) at room temperature separately. The pH (6-7) adjusted solution was stirred with heating (60C) for next 4h and then set aside for crystallization. After four weeks, 0.48g (48% yield) for each 1b and 2b of colourless single crystals were obtained.

According to the analysis of related databases, 3339-73-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Nadeem, Muhammad; Bhatti, Moazzam H.; Yunus, Uzma; Mehmood, Mazhar; Asif, Hafiz Muhammad; Mehboob, Shoaib; Floerke, Ulrich; Inorganica Chimica Acta; vol. 479; (2018); p. 179 – 188;,
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Related Products of 193354-13-1, These common heterocyclic compound, 193354-13-1, name is 5-Iodoindolin-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.

5-Methoxycarbonyl-2-oxindole 5-Iodo-2-oxindole (17 g) was refluxed with 2 g of palladium diacetate, 18.2 g of triethylamine, 150 mL of methanol, 15 mL of dimethylsulfoxide and 2.6 g of DPPP in an atmosphere saturated with carbon monoxide. After 24 hours, the reaction was filtered to remove the catalyst and the filtrate concentrated. The concentrate was chromatographed on silica gel (30% ethyl acetate in hexane). The fractions containing product were concentrated and allowed to stand. The precipitated product was collected by vacuum filtration to give 0.8 g (7%) of the title compound as an off-white solid.

Statistics shows that 5-Iodoindolin-2-one is playing an increasingly important role. we look forward to future research findings about 193354-13-1.

Reference:
Patent; Sugen, Inc.; US6486185; (2002); B1;,
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Reference of 169037-23-4, A common heterocyclic compound, 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, molecular formula is C9H4F3NO3, 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: A mixture of indoline-2,3-dione 1 (1mmol), l-tryptophan (2a) or l-histidine 2b (1mmol) and (E)-(2-nitrovinyl)benzene 3 (1.1mmol) was heated while stirred in [bmim]Br as the reaction medium (3mL) for 1hat 100C. After completion of the reaction (TLC), EtOAc (5mL) was added and the reaction mixture was stirred for 10min. This treatment was repeated and the combined ethyl acetate layers were removed in vacuo. The crude product was purified by recrystallization of the residue from EtOH (compounds 4) or by column chromatography (compounds 5). After extraction of the product, the ionic liquid was dried under vacuum at 80C for 2h to eliminate any water and could be reused for subsequent runs of the reaction.

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; Arumugam, Natarajan; Almansour, Abdulrahman I.; Kumar, Raju Suresh; Periasamy, Vaiyapuri Subbarayan; Athinarayanan, Jegan; Alshatwi, Ali A.; Govindasami, Periyasami; Altaf, Mohammad; Menendez, J. Carlos; Tetrahedron; vol. 74; 38; (2018); p. 5358 – 5366;,
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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. 868066-91-5, name is 5-Bromo-2-methylisoindolin-1-one, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C9H8BrNO

Step B: 2-methyl-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)isoindolin-l-one [0236] 5-Bromo-2-methylisoindolin-l-one (0.112 g, 0.495 mmol), bis(pinacolato)diboron (0.189 g, 0.743 mmol), potassium acetate (0.146 g, 1.486 mmol), and PdCl2(dppf)CH2Cl2 adduct (0.020 g, 0.025 mmol) were suspended in DMA (1.0 mL). The mixture was degassed with N2 and heated in a sand bath at 100C overnight. The reaction mixture was subsequently cooled, diluted with EtOAc (10 mL), and passed through a syringe filter. The filtrate was diluted with water (10 mL) and the layers were separated. The aqueous layer was washed with EtOAc (2 x 5 mL). The organic layers were combined and concentrated in vacuo to give the title compound as a brown residue, which was used without further purification.

According to the analysis of related databases, 868066-91-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; LAWSON, John David; SABAT, Mark; SMITH, Christopher; WANG, Haixia; CHEN, Young K.; KANOUNI, Toufike; WO2013/148603; (2013); A1;,
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Related Products of 18711-13-2, 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 18711-13-2 as follows.

In these schemes, ketone (4.0 equv.) and a catalytic amount of diethylamine (10 drops) are added to a solution of substituted isatin (1.0 equv.) in methanol (5 mL). The mixture is stirred at room temperature until starting material (substituted isatin) disappears completely. The resulting solution is concentrated and applied to flash chromatography eluting with hexane / ethyl acetate to afford pure product in quantitative yield. Further purification is done by recrystallization with hexane / ethyl acetate.; 4,7-Dichloro-3-[2-(4-chlorophenyl-2-oxoethyl)]-3-hydroxyI-l,3-dihydroindol-2-one (YK-4-275): white solid; mp 194-196 0C; 1H NMR (DMSO, 400 MHz) delta 10.96 (s, IH), 7.93 (d, 2H, J = 8.8 Hz), 7.57 (d, 2H, J = 8.8 Hz), 7.30 (d, IH, J = 8.8 Hz), 6.90 (d, IH5 J = 8.8 Hz), 6.47 (s, IH), 4.36 (d, IH, J= 18.4 Hz), 3.71 (d, IH5 J= 18.0 Hz).

According to the analysis of related databases, 18711-13-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GEORGETOWN UNIVERSITY; WO2008/83326; (2008); A2;,
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Synthetic Route of 923590-95-8, A common heterocyclic compound, 923590-95-8, name is 4-Bromoisoindoline hydrochloride, molecular formula is C8H9BrClN, 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.

To a solution of (2S,4R)-BOC-4-hydroxyproline methyl ester (126.3 g, 515 mmol) in DMF (960 mL) at 0 C. was added N,N’-carbonyldiimidazole (83.51 g, 515 mmol). The reaction mixture was stirred at room temperature for 3 h. 4-Bromoisoindoline hydrochloride (120 g, 515 mmol) and diisopropylethylamine (96.3 mL, 540 mmol) were added and the reaction mixture heated to 50 C. for 6 h then allowed to cool to room temperature and stirred overnight. The reaction mixture was partitioned between EtOAc (3 L) and 10% aqueous KHSO4 (6 L), the aqueous re-extracted with EtOAc (2 L) and the combined organic phases washed with 10% aqueous NaHCO3, brine, dried over Na2SO4 and solvent evaporated to a foam (239 g). LRMS (ESI) m/z 471.0 [(M+H)+; calcd for C20H26BrN2O6: 471.1].

The synthetic route of 923590-95-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Holloway, M. Katharine; Liverton, Nigel J.; Ludmerer, Steven W.; McCauley, John A.; Olsen, David B.; Rudd, Michael T.; Vacca, Joseph P.; McIntyre, Charles J.; US2007/27071; (2007); A1;,
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Electric Literature of 3339-73-9, These common heterocyclic compound, 3339-73-9, name is 3-(1,3-Dioxoisoindolin-2-yl)propanoic acid, 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: PhB(OH)2 (6 mg, 0.05 mmol), and xylene (10 mL) were added to a round-bottom flask (100 mL), 1a (90 mg, 0.5 mmol), 2a (97 mg,0.5 mmol). A pressure equalising dropping funnel, in which 4 A molecular sieves (6 g) were placed, was installed onto the flask. Then a condenser was connected to the dropping funnel. After refluxing under stirring for 10 h, the reaction mixture was cooled down to room temperature, and evaporated to remove solvent. The resulting residuewas dissolved in EtOAc (20 mL), and then sequentially washed with 0.1 M NaOH (20 mL), water (20 mL), and brine (20 mL). The organic layer was dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure. The resulting residue was subjected to preparative TLC (eluted with PE/acetone (2/1, v/v), Rf = 0.43) to afford ethyl 2-(N-phenyl-2-(N-phenylacetamido)acetamido)acetate 3a (128 mg 72%) as a pale yellow oil.

Statistics shows that 3-(1,3-Dioxoisoindolin-2-yl)propanoic acid is playing an increasingly important role. we look forward to future research findings about 3339-73-9.

Reference:
Article; Huang, Wenhua; Sha, Wen-Bin; Journal of Chemical Research; vol. 37; 8; (2013); p. 460 – 463;,
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