Author: Jessica.F

Reference of 341988-36-1,Some common heterocyclic compound, 341988-36-1, name is Methyl indoline-6-carboxylate, molecular formula is C10H11NO2, 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 7 1-(2-Bromoethyl)-6-methoxycarbonylindoline To 1,2-dibromoethane (15.7 ml) were added 6-methoxycarbonylindoline (2.41 g) and triethylamine (7.8 ml), and the mixture was stirred at 90¡ã C. for 2 hr. Ethyl acetate (150 ml) was added to the reaction mixture, and the mixture was washed with saturated brine (300 ml) and dried over Na2SO4. Ethyl acetate was evaporated under reduced pressure. The obtained residue was purified by column chromatography to give the title compound (1.71 g). IR v(neat) cm-1; 1713, 1611, 1499.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl indoline-6-carboxylate, its application will become more common.

Reference:
Patent; Matsui, Hiroshi; Kobayashi, Hideo; Azukizawa, Satoru; Kasai, Masayasu; Yoshimi, Akihisa; Shirahase, Hiroaki; US2003/27836; (2003); 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. 89-40-7, name is 5-Nitroisoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Computed Properties of C8H4N2O4

General procedure: The hydrogenation of nitroarenes was carried out in a Teflon-lined stainless steel autoclave equipped with a pressure gauge anda magnetic stirrer. Typically, a mixture of 0.5 mmol nitroarene, 15mol% Co/C-N-X catalyst, 100 L n-hexadecane and 2 mL solventwas introduced into the reactor at room temperature. Air in theautoclave was purged several times with H2. Then, the reactionbegan by starting the agitation (600 r/min) when hydrogen was reg-ulated to 1 MPa after the reaction temperature was reached. Afterreaction, the solid was isolated from the solution by centrifuga-tion. The products in the solution were quantified and identifiedby GC-MS analysis (Shimadzu GCMS-QP5050A equipped with a0.25 mm ¡Á 30 m DB-WAX capillary column).1H NMR and13C NMRdata were obtained on Bruker Avance III 400 spectrometer usingCDCl3or DMSO-d6 as solvent and tetrmethylsilane (TMS) as aninternal standard. The pure product in the scale-up experimentwas obtained by flash column chromatography (petroleum ether and ethyl acetate).

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; Wang, Xi; Li, Yingwei; Journal of Molecular Catalysis A: Chemical; vol. 420; (2016); p. 56 – 65;,
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Application of 100510-65-4, The chemical industry reduces the impact on the environment during synthesis 100510-65-4, name is 6-Amino-3,3-dimethylindolin-2-one, I believe this compound will play a more active role in future production and life.

EXAMPLE G N-Propyl-N’-[2,3-dihydro-3,3-dimethyl-2-oxo-(1H)-indol-6-yl]-urea 3.52 g. (0.02 mole) 6-amino-2,3-dihydro-3,3-dimethyl-(1H)-indolin-2-one are suspended in 40 ml. anhydrous dioxan and mixed at ambient temperature within the course of 10 minutes with a solution of 1.7 g. (0.02 mole) n-propyl isocyanate in 10 ml. dioxan, whereupon a clear solution is formed. Shortly thereafter, the product begins to separate out as a crystalline mass. After 1 hour, the suspension is mixed with ligroin and the precipitate is filtered off with suction, washed with ligroin and diethyl ether and recrystallized from ethanol. Yield 3.91 g. (75% of theory); m.p. 223-225 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; US4985448; (1991); A;,
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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. 3416-57-7, name is 2-(2-Oxopropyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Formula: C11H9NO3

Synthesis of the protected ketone monomer was conducted based on a modification of a previously reported protocol (50). Chloroacetone (10 mE, 12.5 mmol) and the potassium salt ofphthalimide (25.5 g, 13.8 mmol) were added to 150 mE of stirred dry acetone. The solution was then heated to 80 C. for 20 hours, after which it was cooled to room temperature and the acetone was removed in a rotary evaporator. The resulting solid was then redissolved in methylene chloride and washed repeatedly with water. The methylene chloride layer was dried over magnesium sulfate, filtered, and removed using a rotary evaporatot The resulting yellow crude solid was washed with diethyl ether several times until the solid became white; this solid was subsequently dried in a vacuum oven to yield purified intermediate A (Scheme 1A). Intermediate A (lOg, 50 mmol) was then added to 180 mE of toluene along with ethylene glycol (5.85 mE, 100 mmol) and dry para-tolenesulfonic acid (934 mg, 5 mmol) and refluxed for 15 hours. The reaction mixture was cooled to room temperature and the ethylene glycol layer was extracted three times with diethyl ether. The toluene and ether fractions were combined and washed three times with 5% (w/v) NaOH followed by deionized water. The organic layer was dried over magnesium sulfate and solvent was removed in a rotary evaporatot The crude was recrystallized from ethanol to yield pure intermediate B (Scheme 1B). Intermediate B was subsequently added to 100 mE of deionized water along with 15 g of NaOH and refluxed for 2 days, with an additional 60 g of NaOH added slowly over the course ofthe reflux. Afierwards, the reaction mixture was cooled to room temperature and extracted three times with 50 mE dichloromethane. The organic layers were then combined and dried over magnesium sulfate, filtered, and concentrated in a rotary evaporator to yield pure product C (Scheme 1C), a slightly yellow oil. Finally, the monomer was prepared by adding product C (21.1 mE, 180 mmol) to a 20% (w/v) NaOH solution (in water) containing 4-hydroxy TEMPO (10 mg, 0.06 mmol). This reaction mixture was brought to 0 C. in an ice bath and methacryloyl chloride (16.5 mE, 174 mmol) was added drop- wise over 2 hours under nitrogen flow. The ice bath was then allowed to warm to room temperature and the reaction left to stir overnight in darkness. Afier this time, stirring was halted and the product was allowed to collect at the top of the reaction flask. The pure monomer product (along with inhibitor) (shown in Scheme 1 D) was then isolated using a separatory funnel. The monomer was stored in the darkness at -20 C. until use.1H NMR (600 MHz) in DMSO-d5: RNHCH2C(OCH2CH2O)CH3, 1.3 ppm, singlet, 3H;CH2CCH3CONHR?, 2 ppm, singlet, 3H; RNHCH2C(OCH2CH2O)CH3, 3.5 ppm, doublet, 2H; RNHCH2C(OCH2CH2O)CH3, 4 ppm, singlet, 4H; CH2CCH3CONHR?,5.35-5.65 ppm, doublet, 2H; CH2CCH3CONHR?, 6 ppm, sin-glet, 1H.

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; McMaster University; Hoare, Todd; Bakaic, Emilia; Smeets, Niels M.B.; Deng, Xudong; (55 pag.)US2016/151535; (2016); A1;,
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334952-09-9, name is 2-Oxoindoline-6-carboxylic acid, 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. Computed Properties of C9H7NO3

A mixture of 5-(3-aminopyrrolidin-l-yl)-N-(3,4-dimethoxyphenyl)thiazolo[5,4- Patent; F. HOFFMANN-LA ROCHE AG; HERMANN, Johannes Cornelius; LOWRIE, JR., Lee Edwin; LUCAS, Matthew C.; LUK, Kin-Chun Thomas; PADILLA, Fernando; WANNER, Jutta; XIE, Wenwei; ZHANG, Xiaohu; WO2012/130780; (2012); 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. 20780-72-7, name is 4-Bromoisatin, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H4BrNO2

General procedure: To a solution of compound 3 (1.0 mmol) and substituted isatin (1.0 mmol) in ethanol, 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (2.0 mmol) was added. The reaction mixture was stirred at room temperature for about 1 h. The solvent was removed and CH2Cl2 was added, the organic phase was washed with water and brine, dried over Na2SO4. After removal of the solvent, the residue was purified by silica gel chromatography using acetone/petroleum ether (1/2) as the eluent to give the corresponding steroidal pyran?oxindole hybrids.

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; Yu, Bin; Qi, Ping-Ping; Shi, Xiao-Jing; Shan, Li-Hong; Yu, De-Quan; Liu, Hong-Min; Steroids; vol. 88; (2014); p. 44 – 52;,
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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. 201940-08-1, name is tert-Butyl 5-bromoisoindoline-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Formula: C13H16BrNO2

Tert-butyl-5-bromisoindoline-2-carboxylate (20.0 g, 67.09 mmol) was dissolved in Dioxane (200 ml.) and the solution was purged with Argon gas for 10 min. Bispinacalato diborane (34.07 g, 134.18 mmol), KOAc (26.34 g, 268.36 mmol) and Pd(PPh3)4 (7.75 g, 6.70 mmol) were added and the reaction mixture was stirred at 80C for 12 h. Reaction mixture was diluted with water, extracted with EtOAc (1 Ltr. X 2) twice The combined organic layers were washed with water (500 ml_), brine (300 ml_), dried over sodium sulphate and concentrated under vacuo. Crude compound was purified by Combiflash chromatography using 40 g Column and 10% EtOAc in n-Hexane to afford title compound as a White solid 23.0 g (99.30 %). Rf = 0.50 (10% EtOAc in n-Hexane); 1 H NMR (300 MHz, CDCI3): d 7.72-7.65 (m, 2H), 7.31 -7.20 (m, 1 H), 4.70-4.60 (m, 4H), 1 .40 (s, 9 H), 1 .37 (s, 12H).

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 201940-08-1.

Reference:
Patent; NOVARTIS AG; JIRICEK, Jan; NG, Shuyi Pearly; RAO, Srinivasa P S; (126 pag.)WO2019/244049; (2019); A1;,
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Some common heterocyclic compound, 181140-34-1, name is (R)-(-)-N-(2,3-Epoxypropyl)phthalimide, molecular formula is C11H9NO3, 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: (R)-(-)-N-(2,3-Epoxypropyl)phthalimide

A mixture of (R)-N-(2,3-epoxypropyl)-phthalimide (1.02 g, 5.0 mmol), phenol (5.0 mmol), p-xylene (2 mL) and DBU (0.05 mL) was stirred under N2 at 120 C. for 8 h. After cooling to 80 C. iPrOH (20 mL) and anhydrous hydrazine (1 mL) were added and the mixture was heated at 80 C. for 4 h. The reaction mixture was cooled to RT, 0.5N aq. NaOH (50 mL) was added, extracted with EtOAc (100 mL). Extract was washed with 0.5N aq. NaOH (50 mL), brine (50 mL), dried over Na2SO4 and evaporated. The residue was triturated with cold Et2O, the solid was collected by filtration, dried in vacuum.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 181140-34-1, its application will become more common.

Reference:
Patent; Gregor, Vlad E.; Liu, Yahua; Anikin, Alexey; McGee, Danny Peter Claude; Mikel, Charles; McGrath, Douglas Eric; Vavilala, Goverdhan Reddy; Pickens, Jason C.; Kadushkin, Alexander; Jiang, Luyong; Thiruvazhi, Mohan Santhanam; Zozulya, Sergey; Vairagoundar, Rajendran; Zhu, Tong; Chucholowski, Alexander; Webb, Thomas; Gantla, Vidyasagar Reddy; Yan, Zheng; US2008/171769; (2008); A1;,
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Related Products of 1254319-51-1,Some common heterocyclic compound, 1254319-51-1, name is 6-Bromo-2-methylisoindolin-1-one, molecular formula is C9H8BrNO, 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.

(S)-tert-Butyl 4-( 1 -amino- 1 -oxo-3-(4-(4,4,5 ,5 -tetramethyl- 1 ,3 ,2-dioxaborolan-2- yl)phenyl)propan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (Example 16, step (i), 300 mg), 6-bromo-2-methylisoindolin-l-one (Example 30, step (i), 131 mg) and potassium acetate (171 mg) in a mixture of acetonitrile (15 mL) and water (5 mL) was stirred under nitrogen at 900C with 1,1 delta(di-fert-butylphosphino)ferrocene palladium dichloride (378 mg). After 4 h the reaction mixture was cooled to room temperature and diluted with water (50 mL). The products were extracted with ethyl acetate (3 x 50 mL) and the combined extracts dried over magnesium sulfate and concentrated to afford the sub-titled compound (200 mg).m/e (MultiMode+) 436 [M+2Eta-BOC]+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Bromo-2-methylisoindolin-1-one, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; FORD, Rhonan; METE, Antonio; MATHER, Andrew; MILLICHIP, Ian; WO2010/128324; (2010); A1;,
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Electric Literature of 112656-95-8, 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. 112656-95-8, name is 7-Nitroindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Add 7-nitroisatin 3 (10g, 0.052mol) and tetrahydrofuran (200mL) to a 250mL reaction flask, add sodium borohydride (2.4g, 0.061mol) in portions, and add tetrachloride in portions under cooling in an ice bath. Zirconium (42.4 g, 0.182 mol).The temperature was raised to room temperature for 18 hours, and the starting material disappeared by HPLC.1 mol / L hydrochloric acid (50 mL) was slowly added dropwise to the reaction flask, stirred for 30 minutes, ethyl acetate (100 mL) was added, 100 mL of water was added, insoluble matter was filtered off, the filtrate was left to separate and the organic layer was washed with 100 mL of water, and concentrated A yellow crude product was obtained, which was recrystallized from ethyl acetate and n-heptane to obtain 7.2 g of yellow crystals with a yield of 86% and a purity of 98.2%.

The synthetic route of 7-Nitroindoline-2,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangsu Suli Fine Chemical Co., Ltd.; Wang Jingli; Yang Kai; Fei Zhongbo; Cao Wenli; Wang Liyang; Ding Shaocong; (6 pag.)CN110845388; (2020); A;,
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