Tag: M.W=100-200

Related Products of 21857-45-4, A common heterocyclic compound, 21857-45-4, name is 5-Methoxyindoline, molecular formula is C9H11NO, 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 100 mL round- bottomed flask, flushed with nitrogen, were added 17 (91 mg, 0.5 mmol), 5-methoxyindoline (82 mg, 0.55 mmol), BuOH (10 mL), and 2-3 drops of cone. HC1. The reaction mixture was heated at reflux with stirring for 12 h until the starting material 17 disappeared (TLC). The reaction solution was allowed to cool to room temperature; the solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel with hexane: acetyl acetate = 20: 1 as the eluent. Fractions containing the product (TLC) were combined and evaporated to afford 93 mg (63%) 8 as a white powder: mp 201.1-202.3 C; Rf 0.5 (AcOEt/Hexane 3 : 1); 1H NMR (DMSO-d6) delta 2.42 (s, 3 H), 2.53 (s, 3 H), 3.25 (t, 2 H), 3.75 (s, 3 H), 4.39 (t, 2 H), 6.79 (t, 2 H), 6.89 (d, 1 H), 8.48 (d, 1 H), Anal. Ci7H17N302

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; DUQUESNE UNIVERSITY OF THE HOLY SPIRIT; GANGJEE, Aleem; (111 pag.)WO2016/100495; (2016); A1;,
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Application of 603-62-3, 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 603-62-3 as follows.

Step 1: To a solution of potassium hydroxide (16.1 g, 286 mmol) in water (500 mL), was added 3-nitrophthalimide (25.0 g, 130 mmol) in portion at 0 C. The suspension was stirred at 0 C. for 3 hrs, and then heated to 30 C. for 3 hrs. To the solution, was added HCl (100 mL, 6N). The resulting suspension was cooled to 0 C. for 1 hr. The suspension was filtered and washed with cold water (2*10 mL) to give 3-nitro-phthalamic acid as a white solid (24.6 g, 90% yield): 1H NMR (DMSO-d6) delta 7.69 (brs, 1H, NHH), 7.74 (t, J=8 Hz, 1H, Ar), 7.92 (dd, J=1, 8 Hz, 1H, Ar), 8.13 (dd, J=1, 8 Hz, 1H, Ar), 8.15 (brs, 1H, NHH), 13.59 (s, 1H, OH); 13C NMR (DMSO-d6) delta 125.33, 129.15, 130.25, 132.54, 136.72, 147.03, 165.90, 167.31.

According to the analysis of related databases, 603-62-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Muller, George W.; Schafer, Peter H.; Man, Hon-Wah; Zhang, Ling-Hua; Gandhi, Anita; Chopra, Rajesh; US2012/230983; (2012); A1;,
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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.

1-[2-Oxo-5-(pyrrolidine-1-carbonyl)-1,2-dihydro-indol-3-ylidenemethyl]-2,5,6,7-tetrahydro-pyrrolo[3,4-c]pyridin-4-one PyBOP (3.5 g, 6.72 mmol) was added to a mixture of 5-carboxy-2-oxindole (1 g, 5.6 mmol), pyrrolidine (0.5 mL, 6.2 mmol) and triethylamine (2.0 mL, 14 mmol) in dichloromethane. After stirring at room temperature for 4 hours, the reaction was diluted with more dichloromethane, washed with saturated sodium bicarbonate and brine, dried and concentrated. The residue was purified by column chromatography to give 5-(pyrrolidine-1-carbonyl)-1,3-dihydro-indol-2-one. 1H NMR (300 MHz, DMSO-d6) delta 10.52 (br s, 1H, NH), 7.37 (m, 2H), 6.80 (d, J=8.5 Hz, 1H), 3.49 (s, 2H, CH2), 3.42 (m, 4H, 2xCH2), 1.81 (m, 4H, 2*CH2). MS-El m/z 230 [M+].

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; Tang, Peng Cho; Miller, Todd A.; Li, Xiaoyuan; Zhang, Ruofei; Cui, Jinrong; Huang, Ping; Wei, Chung Chun; US2002/42427; (2002); 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. 954255-04-0, name is 5,6-Difluoroindoline, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C8H7F2N

Example 46 5-(6-(5,6-difluoroindoline-1-carbonyl)pyrimidin-4-ylamino)-1,3-dihydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-2′(1’H)-one 0.10 g (0.24 mmol) 6-(2′-oxo-1,1′,2′,3-tetrahydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-5-ylamino)pyrimidine-4-carboxylic acid hydrochloride, 50 mg (0.26 mmol) 5,6-difluoro-2,3-di-hydro-1H-indole, 0.10 mL (0.72 mmol) TEA and 80 mg (0.25 mmol) TBTU in 1.8 mL DMF were stirred overnight at RT. The purification was carried out by preparative HPLC-MS. The product-containing fractions were combined and lyophilised. Yield: 45 mg (36% of theory) ESI-MS: m/z=511 (M+H)+ Rt (HPLC-MS): 1.61 min (method C)

According to the analysis of related databases, 954255-04-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2011/21500; (2011); A1;,
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Electric Literature of 20876-36-2, 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. 20876-36-2, name is 5-Aminoindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 1 A mixture of 5-aminooxindol (14 g), 29 g of bis(beta-bromoethyl)amine.hydrobromide in 250 ml of ethanol was stirred under reflux for 8 hours and allowed to stand overnight at room temperature. To the mixture was added sodium carbonate (10.1 g) and the mixture was stirred further for 8 hours under reflux. After cooling to room temperature, crystals which precipitated were collected by filtration and recrystallized from a mixture of water and ethanol to give 16 g of 5-(1-piperazinyl)oxindol.hydrobromide. Pale yellow powdery crystal NMR (200 MHz, DMSO-d6) delta: 3.30 (8H, s), 3.47 (2H, s), 6.78 (1H, d, J=8.5 Hz), 6.90 (1H, dd, J=8.5 Hz, 2 Hz), 7.04 (1H, d, J=2 Hz), 8.88 (2H, brs), 10.27 (1H, s)

The synthetic route of 5-Aminoindolin-2-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Otsuka Pharmaceutical Co., Ltd.; US4737501; (1988); A;,
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Related Products of 20870-79-5, 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. 20870-79-5, name is 5-Nitroindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Appel?s salt (Scheme 2, 1; 4,5-dichloro-1,2,3-dithiazolium chloride; 15.76 mmol) was added to asolution of each appropriate 2-oxindole derivative (Scheme 2, 2a-d; 14.33 mmol) in CH2Cl2 (20 mL).After a few minutes, the uncolored mixture turned to a dark red color, and was stirred at roomtemperature for 18 h. The solvent was evaporated under reduced pressure, and the crude productwas dissolved with acetone (a minimum of 30 mL), and then precipitated with water (300 mL).The heterogeneous mixture was filtered in a vacuum, and the red solid was washed three times withwater (25 mL). This solid was finally dried over phosphorus pentoxide in a vacuum in a desiccator.

The chemical industry reduces the impact on the environment during synthesis 5-Nitroindolin-2-one. I believe this compound will play a more active role in future production and life.

Reference:
Article; Letribot, Boris; Delatouche, Regis; Rouillard, Herve; Bonnet, Antoine; Cherouvrier, Jean-Rene; Domon, Lisianne; Besson, Thierry; Thiery, Valerie; Molecules; vol. 23; 6; (2018);,
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Reference of 3485-84-5, A common heterocyclic compound, 3485-84-5, name is N-Vinylphthalimide, molecular formula is C10H7NO2, 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.

A 20-mL, microwave reaction vessel was charged with (4-bromopyridin-3-yl)-(4-(trifluoro methyl)phenyl)methanol (0.87 g, 2.62 mmol), 2-vinylisoindoline-1,3-dione (499 mg, 2.88 mmol), Pd(dba)2 (75.3 g, 0.13 mmol), 2-(dicyclohexyl-phosphino)biphenyl (91.8 mg, 0.26 mmol), NEt3 (0.44 ml, 3.14 mmol), and DMF (2 mL). The mixture was purged with argon and heated in microwave synthesizer at 150 C. for 1 h. The reaction mixture was partitioned between water and EtOAc. The EtOAc layer was separated and aqueous layer was extracted again with EtOAc. The combined organic layers were washed with saturated NaHCO3, dried over Na2SO4, filtered, and concentrated in vacuo. The resulting residue was purified by silica gel chromatography (0-10% MeOH in DCM) to give the mixture (0.4 g) of (E)-2-(2-(3-(hydroxy(4-(trifluoromethyl)phenyl)methyl)pyridin-4-yl)-vinyl) isoindoline-1,3-dione and 2-(2-(3-(hydroxy(4-(trifluoromethyl)phenyl)-methyl)pyridin-4-yl)ethyl)isoindoline-1,3-dione as a light yellow semi-solid. MS (ESI pos. ion) m/z: 425 and 427.

The synthetic route of 3485-84-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nishimura, Nobuko; Norman, Mark H.; Tamayo, Nuria; Tang, Phi; Bo, Yunxin Y.; US2009/82358; (2009); A1;,
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Synthetic Route of 480-91-1,Some common heterocyclic compound, 480-91-1, name is Isoindolin-1-one, molecular formula is C8H7NO, 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.

Sodium hydride 60% in mineral oil (0.750 mg, 30.0 mmol) and dry THF (150 ml) were added to a two-necked round-bottomed flask. Isoindolin-1-one (5) (2.50 g, 18.8 mmol) was added to the suspension at 0 C under N2. The reaction mixture wasstirred for 30 min at 0 C, and then potassium bromomethyl trifluoroborate (3.00 g, 15.0 mmol) was added to the reaction mixture in one portion and stirred for 30 min at 0 C. The reaction mixture was warmed to room temperature and refluxed for 48 h. The reaction mixture was cooled to 0 C and quenched by KHF2 (3.0 M) in H2O (14 mL). The reaction mixture was stirred at room temperature for 2 h. The solvents were removed under vacuum, and residue was dissolved in ethyl acetate (100 mL) and filtered. The solid obtained was triturated with boiling acetone (3 x 50 mL) and the resulting white powder was washed with cold ether (3 x 20 mL) and dried to give the potassium N-methyltrifluoroborate isoindolin-1-one (6) as white solid (2.54 g, 65%): mp: 229-234 C; IR (KBr, neat): 3032, 2936, 2897, 2879, 1658, 1590, 1473, 1455, 1426, 1415, 1306, 1228, 1210, 1099, 1069, 1011, 996, 760, 726, 538 cm-1; 1H NMR (DMSO-d6, 400 MHz) delta = 7.59 (d, J = 8.0 Hz, 1H), 7.53-7.46 (m, 2H), 7.42-7.39 (m, 1H), 4.38 (s, 2H), 2.47 (s, 2H); 13C NMR (DMSO-d6, 100 MHz) delta = 169.9, 144.0, 131.5, 131.2, 127.5, 123.7, 122.7, 44.8; 11B NMR (DMSO-d6, 128.37 MHz) delta = 3.46 (br s); 19F NMR (DMSO-d6, 376.49 MHz): delta = 138.67. HRMS (ESI-TOF) m/z calcd. for C9H8BNOF3 (M-K) 214.0651; found 214.0661.

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

Reference:
Article; Nadaf, Rashid N.; Seapy, Dave G.; Synthetic Communications; vol. 44; 14; (2014); p. 2012 – 2020;,
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Synthetic Route of 3485-84-5, These common heterocyclic compound, 3485-84-5, name is N-Vinylphthalimide, 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: In a sealed tube under argon atmosphere, were introducedcompound 4 (4.74 g, 20 mmol), DMF (20 mL), triethylamine(11.16 mL, 80 mmol), palladium diacetate (225 mg, 1 mmol), tri(otolyl)-phosphine (609 mg, 2 mmol) and N-vinylphthalimide (5.20 g,30 mmol). The mixturewas stirred at 110 C for 3 h and hydrolyzed.The formed solid was solubilized in CH2Cl2, washed with water andbrine, dried over MgSO4 and evaporated under reduced pressure.The crude productwas recrystallized from acetonitrile to afford 7 asa white solid (91% yield)

Statistics shows that N-Vinylphthalimide is playing an increasingly important role. we look forward to future research findings about 3485-84-5.

Reference:
Article; Landagaray, Elodie; Ettaoussi, Mohamed; Rami, Marouan; Boutin, Jean A.; Caignard, Daniel-Henri; Delagrange, Philippe; Melnyk, Patricia; Berthelot, Pascal; Yous, Said; European Journal of Medicinal Chemistry; vol. 127; (2017); p. 621 – 631;,
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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. 3891-07-4, name is 2-(2-Hydroxyethyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., SDS of cas: 3891-07-4

Preparation of Ethyl 4-[2-(PHTHALIMIDO) ETHOXY] ACEFOACETATE (X1 A 250 mL two-necked flask, equipped with a magnetic stirring bar, thermometer and a pressure equalized addition funnel was charged with 75 mL of tetrahydrofuran under nitrogen atmosphere. 7.53 g Sodium hydride (60% dispersed in oil) was added and the resulting suspension was cooled to-10 C and 20 g of N- (2-HYDROXYETHYL) PHTHALIMIDE was added slowly over 5 minutes. The resulting slurry was stirred at-10 C for 30 minutes. To this mixture a solution of 16.35 g ethyl 4-chloroacetoacetate in 30 ML of TETRAHYDRAFURAN was added at-10 C in 40 minutes. The reaction mixture was warmed to room temperature and then stirred at room temperature for 18 hours. The reaction mixture was placed in an ice bath and quenched by dropwise addition of 10 mL ethanol. The mixture was then poured into 150 mL of IN hydrochloric acid solution in crushed ice and 200 ML of ethyl acetate was added. The resulting mixture was transferred into a separatory funnel and the aqueous phase was separated. The organic phase was first washed with 70 mL of ethyl acetate was added. The resulting mixture was transferred into a separatory funnel and the aqueous phase was separated. The organic phase was first washed with 70 mL of 5 wt. % OF NAHC03 solution, then with 150 ML of water, dried over 5 G of MgS04. MgS04 was filtered off and the filtrate was concentrated in vacuo to give a light brown oily product. The oil was washed with 15 mL of hexane to remove the mineral oil to give 17.2 g of ethyl 4- [2- (phthalimido) ethoxy] acetoacetate light brown product. (yield 51%, rel. compound purity > 80%). IR (KBR, CM~L) : 2995 and 1716. 1H-NMR (CDC13) 6 7.76 (dd, 2H), 7.65 (dd, 2H), 4.11 (S, 2H), 4.02 (q, 2H), 3.80 (t, 2H), 3.70 (t, 2H), 3.37 (s, 2H), 1. 16 (t, 3H). 13C-NMR (CDC13) 8 201.7, 168.4, 167.2, 134.3, 132.2, 123.5, 75.6, 68.7, 61.6, 46.0, 37.4, 14.3.

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; EOS ECZACIBASI OZGUN KIMYASAL URUNLER SANAYI VE TICARET A.S.; WO2004/58711; (2004); A1;,
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