Month: May 2021

Electric Literature of 18711-15-4, A common heterocyclic compound, 18711-15-4, name is 4,6-Dichloroisatin, molecular formula is C8H3Cl2NO2, 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.

2.25 g of magnesium for a Grignard reaction in 15 ml of anhydrous THF are placed in a round-bottomed flask equipped with a mechanical stirrer, and under a stream of nitrogen. A mixture of 13.6 g of 5-bromobenzofuran in 35 ml of anhydrous THF is then added. The mixture is stirred for one hour, followed by addition of a solution of 5 g of 4,6-dichloro-1H-indole-2,3-dione in 50 ml of anhydrous THF. The mixture is stirred at room temperature for 4 hours 30 minutes. Water is added and the resulting mixture is extracted with ethyl acetate. The organic phase is separated out, dried over Na2SO4, filtered and evaporated under vacuum. The residue is taken up in ethyl acetate and washed with 1N sodium hydroxide solution. The organic phase is dried over Na2SO4, filtered and evaporated under vacuum. The solid is taken up in ethyl ether and filtered off. 4.2 g of expected product are obtained. TLC: 6/4 hexane/EtOAc, Rf=0.35

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; US2012/40996; (2012); A1;,
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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. 1029691-06-2, name is 2-(3-Oxocyclopentyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Safety of 2-(3-Oxocyclopentyl)isoindoline-1,3-dione

To a stirred solution of 200 mg (0.87 mmol) of 2-(3-oxocyclopentyl)isoindoline-1,3-dione (CAS 1029691-06-2) in 5 mL of DCM at 0C were added 10mg (0.26 mmol) of NaBH4 and then lmL of MeOH. Themixture was stirred at this temperature for 0.5 h. 20 mL of H20 was added and the mixture was extractedwith DCM. The combined organic layers were dried over Na2SO4 and then concentrated under vacuum. The residue was purified by silica gel column chromatography (PE/ EA = 2/1) to give 96 mg of the product as a white solid.MS (ESI+): 232.0 [M+H].?H NMR (400 MHz, DMSO-d6) ppm: 7.76-7.83 (m, 5H), 4.80 (d, J = 5.2 Hz, 1H), 4.43 (m, 1H), 4.06 (m, 1H), 1.64-2.15 (m, 6H).

The synthetic route of 1029691-06-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BASILEA PHARMACEUTICA AG; POHLMANN, Jens; STIEGER, Martin; REINELT, Stefan; LANE, Heidi; (286 pag.)WO2016/128465; (2016); A1;,
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Application of 141452-01-9, A common heterocyclic compound, 141452-01-9, name is Methyl indoline-5-carboxylate, molecular formula is C10H11NO2, 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.

Reference Example 15 methyl 1-(6-chloropyrimidin-4-yl)-2,3-dihydro-1H-indole-5-carboxylate; A mixture of methyl 2,3-dihydro-1H-indole-5-carboxylate (5.19 g), 4,6-dichloropyrimidine (4.37 g), and ethanol (50 mL) was stirred overnight with heating under reflux, and concentrated under reduced pressure. To the residue were added saturated aqueous sodium hydrogen carbonate solution and ethyl acetate, and the mixture was stirred for 30 min. Insoluble materials were collected by filtration to give the title compound (5.87 g, 69%) as a white solid. 1H-NMR (300 MHz, CDCl3)delta:3.32 (t, J=8.7 Hz, 2 H), 3.91 (s, 3 H), 4.08 (t, J=8.7 Hz, 2 H), 6. 66 (s, 1 H), 7.90 (s, 1 H), 7.95 (d, J=8.5 Hz, 1 H), 8.46 (d, J=8.5 Hz, 1 H), 8.64 (s, 1 H).

The synthetic route of 141452-01-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2399914; (2011); A1;,
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Some common heterocyclic compound, 104618-32-8, name is 2-(4-Oxocyclohexyl)isoindoline-1,3-dione, molecular formula is C14H13NO3, 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: C14H13NO3

Example 3 3-Amino-6-methoxy-1,2,3,4-tetrahydrocarbazole hydrochloride Reaction of 4-methoxyphenyl hydrazine hydrochloride (0.87 g, 5.0 mmol) with 4-phthalimido-cyclohexanone (1.22 g, 5.0 mmol) in ethanol (20 ml) heated under reflux for 2 hr, followed by cooling and removal of the precipitated solid by filtration gave 3-phthalimido-6-methoxy-1,2,3,4-tetrahydrocarbazole (1.62 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 104618-32-8, its application will become more common.

Reference:
Patent; Smithkline Beecham plc; US5827871; (1998); A;,
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Synthetic Route of 22190-33-6, 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. 22190-33-6, name is 5-Bromoindoline, This compound has unique chemical properties. The synthetic route is as follows.

Step 2. fert-Butyl-5-bromoindoline-l-carboxylate (BI12): To a stirred solution of 5- bromo-indoline (3.0 g , 15mmol) in acetonitrile (100 ml), was added DMAP (0.185 g , 1.522 mmol) and di-ieri-butyl dicarbonate (3.98 g, 18.3 mmol) and the reaction was stirred at RT for 16 h. The reaction mixture was concentrated on reduced pressure to obtain a residue which was diluted with diethyl ether and washed with water and brine solution (2X). The combined ether layer was dried over anhydrous Na2S04 and concentrated under reduced pressure to afford the crude product as an off-white solid, which was used in the next step without further purification (3.0 g).

The chemical industry reduces the impact on the environment during synthesis 5-Bromoindoline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; DOW AGROSCIENCES LLC; LO, William C.; HUNTER, James E.; WATSON, Gerald B.; PATNY, Akshay; IYER, Pravin S.; BORUWA, Joshodeep; WO2014/100163; (2014); 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. 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, A new synthetic method of this compound is introduced below., Recommanded Product: 2-Oxoindoline-5-carboxylic Acid

General procedure: To a solution of 4 (1.77 g, 10 mmol) in 120 mL ofdichloromethane and 10 mL of DMF was added 4-methylmorpholine or DIEA (10 mL), TBTU (4.81 g, 15mmol) and aniline derivatives (11 mmol). The mixture wasstirred under room temperature for 18 h and washed in turnwith 5% sodium carbonate solution, 5% citric acid solutionand saturated sodium chloride solution. After dried byanhydrous sodium sulfate, the organic layer was evaporatedto dryness. The residue was purified with flash chromatography(CH2Cl2:CH3OH, 50:1) to afford intermediates 5a-5l, which were used in the next step in short time. To asolution of compounds 5a-5l (1.0 mmol) in 10 mL methanolwas added piperidine (30 muL) and 1H-pyrrole-2-carbaldehyde/furan-2-carbaldehyde (1.0 mmol). The mixturewas stirred at 60 C for 5 h and cooled to room temperature.After kept in fridge overnight, the target compounds 6a-6land 7a-7l were obtained in high yields.

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; Ai, Juntao; Lv, Meng; Li, Xiaohui; Chen, Zhuo; Hu, Gaoyun; Li, Qianbin; Medicinal Chemistry Research; vol. 27; 1; (2018); p. 161 – 170;,
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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. 550-44-7, name is 2-Methylisoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 2-Methylisoindoline-1,3-dione

Add a nitrating agent to N-methylphthalimide at -5 C, and react at 40 C for 4h, then extract with an extraction solvent dry,N-methyl-4-nitrophthalimide is formed.The extraction solvent is ethyl acetate and dichloromethane, and the weight ratio is 1: 0.6. The weight ratio of the extraction solvent and N-methylphthalimide is 1: 1.

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 550-44-7.

Reference:
Patent; Shandong Juancheng Fangyuan Bearing Chemical Co., Ltd.; Li Zhi; Zhang Hongyuan; Zhang Heji; (13 pag.)CN110437131; (2019); A;,
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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 41910-64-9 as follows. Recommanded Product: 41910-64-9

General procedure: To the appropriate cyclic amine (20 mmol) in hexane (15 mL) amyl nitrite (60 mmol, 7 g, 8 mL) was added in one portion. The resulting mixture was stirred for 30 min at room temperature. The precipitated solid was collected by filtration, washed with hexane, dried and used for preparation of corresponding N-aminoindolines 3a-d and N-amino-1,2,3,4-tertahydroquinolines 7a,b without purification.

According to the analysis of related databases, 41910-64-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; S?czewski, Franciszek; Wasilewska, Aleksandra; Hudson, Alan L.; Ferdousi, Mehnaz; Rybczy?ska, Apolonia; Boblewski, Konrad; Lehmann, Artur; Acta poloniae pharmaceutica; vol. 72; 2; (2015); p. 277 – 287;,
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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. 132898-96-5, name is 2,3-Dioxoindoline-5-sulfonyl chloride, This compound has unique chemical properties. The synthetic route is as follows., Formula: C8H4ClNO4S

To a slurry of 2,3-dioxomdoline-5-sulfonyl chloride (Lee, D. et al. J. Med. Chem. 2001, 44, 2015) (7,07 g, 28.8 mmol) m CH2Cl2 (288 mL) at rt was added neopentyl alcohol (7.61 g, 86.3 mmol) then pyridine (11.6 mL, 143 mmol). The reaction was stirred at rt for 22 hours, becoming a clear, oiange solution. The reaction was diluted with ILO (300 mL) and extracted with EtOAc (2 chi 600 mL). The combined organic extracts were washed with 0.1 M aqueous HCl (3 * 300 mL), saturated aqueous NaHCO3 (300 mL), and saturated aqueous NaCl (300 mL), then dried over Na2SO4, filtered, and concentrated in vacuo to provide the title compound as a yellow solid (6.40 g, 92%). 1H NMR (400 MHz, CDClj): consistent; MS (ES ) m’z 315.1 (,VHH2O)

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 132898-96-5.

Reference:
Patent; WYETH LLC (FORMERLY KNOWN AS WYETH); DOLLINGS, Paul, Jeffrey; DONNELL, Andrew, Forrest; GILBERT, Adam, Matthew; ZHANG, Minsheng; HARRISON, Boyd, Lynn; STANTON III, Charles, John; O’NEIL, Steven, Victor; HAVRAN, Lisa, Marie; CHONG, Dan, Chaekoo; WO2010/77839; (2010); A1;,
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These common heterocyclic compound, 19155-24-9, name is 3,3-Dimethylindolin-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. COA of Formula: C10H11NO

EXAMPLE 10 5-Bromo-3,3-dimethyl-1,3-dihydro-2H-indol-2-one: 3,3-Dimethyl-1,3-dihydro-2H-indol-2-one (1.12 g, 6.95 mmol) was dissolved in chloroform and stirred at room temperature under nitrogen. Bromine (1.12 g) was added and the mixture was heated under reflux until HBr evolution ceased and the bromine colour was discharged from the solution. The solution was washed with sodium metabisulphite solution and sodium hydrogen carbonate solution, dried (MgSO4), filtered and concentrated to dry under reduced pressure to give 5-bromo-3,3-dimethyl-1,3-dihydro-2H-indol-2-one as a yellow solid. 1 H NMR (CDCl3) d1.39 (6H s), 6.8 (1H d), 7.3 (2H m), 7.9 (1H broad)

The synthetic route of 3,3-Dimethylindolin-2-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Eli Lilly and Company Limited; US5773448; (1998); A;,
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Indoline | C8H9N – PubChem