Tag: M.W=200-300

These common heterocyclic compound, 5181-35-1, name is 2-(2-Bromoethoxy)isoindoline-1,3-dione, 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. category: indolines-derivatives

To a solution of 2-(2-bromoethoxy) isoindoline-l,3-dione (10 g, 37 mmol) and tert-buty 2-(lH-tetrazol-5-yl)ethylcarbamate (7.88 g, 37 mmol) in dimethyl formamide (50 ml) was added cesium carbonate ((14.48 g, 44 mmole) in portion wise at 25-30 C under stirring. The reaction mixture was stirred for further 16 hours and filtered; the filtrate was slowly poured into chilled water (400 ml) under stirring and continued stirring for 30 minutes. The formed precipitates of compound were filtered and washed with water (40 ml). The solid compound was dried at 40C for 2 hour under high vacuum, yielded 12 g. The compound was column purified using hexane and acetone as an eluent. The mixture was isolated at 10-15% concentration of acetone in hexane to yield 10 g of 2-{2-[5-(2-tertiary butoxy carbonyl aminoethyl)-2H-tetrazol-2-yl]ethoxy}-lH-isoindole-l,3(2H)-dione and 2-{2-[5-(2-tertiary butoxy carbonyl aminoethyl)-lH-tetrazol-l-yl]ethoxy}-lH-isoindole-l,3(2H)-dione in 67% yield Analysis: Mass: 403 (M+l); for Molecular weight: 402 and Molecular formula: C18H22N6O5..; Hydrazine hydrate monohydrate (1.86 ml, 037.3 mmol) was added to a solution of 2-{2-[5-(2- tertiary-butoxy-carbonyl-aminoethyl)-2H-tetrazol-2-yl]ethoxy}-lH-isoindole-l,3(2H)-dione and 2- {2-[5-(2-tertiary-butoxy-carbonyl-aminoethyl)-lH-tetrazol-l-yl]ethoxy}-lH-isoindole-l,3(2H)- dione (10 g, 24.8 mmol, obtained from step 1) in dichloromethane (10 ml) under stirring at room temperature. After completion of 2 hours of stirring at same temperature the TLC confirms the completion of reaction. The reaction mass was filtered and the solid was washed with dichloromethane (50 ml). The collected filtrate was concentrated at 40C under vacuum to yield 6.75 g of the product, which was used further without any purification. Analysis: Mass: 273 (M+l); for Molecular weight: 272 and Molecular formula: CioH2oN603; To a solution of (2S,5R)-6-(benzyloxy)-7-oxo-l,6- diaza-bicyclo[3.2.1]octane-2-carboxylic acid (6.2 g, 22 mmol) in dimethylformamide (50 ml) was added EDC.HC1 (6.45 g, 33.6 mmol) at ambient temperature under stirring. To this was added N- methyl morpholine (7.23 ml, 67.3 mmol) followed by HOBT (3.04 g, 22 mmol) under stirring and reaction mixture was stirred for 5 minutes and cooled to 15C and a solution of mixture of tert- butyl (2-{ l-[2-(aminooxy)ethyl]-lH-tetrazol-5-yl}ethyl)carbamate and tert-buty (2-{2-[2- (aminooxy)ethyl]-2H-tetrazol-5-yl}ethyl)carbamate (6.72 g, 24.7 mmol) in dimethylformamide (12 ml) was slowly added and allowed to reach ambient temperature and stirred for 16 hours. The progress of reaction was monitored by TLC, after complete conversion of starting material the reaction mixture was slowly poured onto chilled water (500 ml) and extracted with ethyl acetate (2×150 ml). The combined organic layer was washed with brine (75 ml) and organic layer was dried over anhydrous sodium sulfate. The organic layer was concentrated on rotavapour to provide 4.2 g of crude compound. The crude compound was column purified by using hexane and acetone as an eluent. The non-polar spot isolated at 10-15% concentration of acetone in hexane yielded 1.6 g of (2S,5R)-N-{2-[5-(2-tertiary butoxy carbonyl aminoethyl)-2H-tetrazol-2-yl]ethoxy}-6- benzyloxy-7-oxo-l,6-diazabicyclo[3.2.1]octane-2-carboxamide. The polar spot isolated at 20-25% concentration of acetone in hexane and the pure fractions were collected and concentrated on Rota evaporator to yield 1.4 g of (2S,5R)-N-{2-[5-(2-tertiary butoxy carbonylaminoethyl)-lH-tetrazol-l- yl]ethoxy}-6-benzyloxy-7-oxo-l,6-diazabicyclo[3.2.1] octane-2-carboxamide as white compound, in 25% yield. Analysis: Mass: 531 (M+l); for Molecular weight: 530 and Molecular formula: C24H34N8O6. 1H NMR (DMSO-de): delta 9.30 (s, 1H), 7.43-7.33 (m, 5H), 5.05-5.02 (m, 1H), 4.90-4.83 (m, 3H), 4.47-4.43 (m, 2H), 3.92-3.91 (d, 1H, J= 7.2 Hz), 3.59-3.57 (m, 2H), 3.30 (s, 1H), 3.11-3.08 (m, 2H), 2.99-2.97(m, 1H), 2.71-2.68 (m, 1H), 2.29-2.24 (m, 2H),m 2.04-1.89 (m, 3H), 1.49 (s, 9H).

The synthetic route of 2-(2-Bromoethoxy)isoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WOCKHARDT LIMITED; TADIPARTHI, Ravikumar; PATIL, Vijaykumar Jagdishwar; DEKHANE, Deepak; SHAIKH, Mohammad Usman; BIRAJDAR, Satish; DOND, Bharat; PATEL, Mahesh Vithalbhai; (100 pag.)WO2017/81615; (2017); A1;,
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Electric Literature of 552330-86-6, 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. 552330-86-6, name is 5-Bromoisoindolin-1-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Step B: 5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)isoindolin-l-one [0231] 5-Bromoisoindolin-l-one (0.066 g, 0.311 mmol), bis(pinacolato)diboron (0.119 g, 0.467 mmol), potassium acetate (0.092 g, 0.934 mmol), and PdCl2(dppf)CH2Cl2 adduct (0.013 g, 0.016 mmol) were suspended in DMA (0.6 mL), degassed with N2, and stirred 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 brown oil, which was used without further purification.

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, 5-Bromoisoindolin-1-one, other downstream synthetic routes, hurry up and to see.

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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Electric Literature of 200049-46-3,Some common heterocyclic compound, 200049-46-3, name is 7-Bromo-2,3-dihydro-isoindol-1-one, molecular formula is C8H6BrNO, 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 1 -(3 -bromo- 1 -(tetrahydro-2H-pyran-4-yl)-6, 7-dihydro- 1H-pyrazolo[4, 3-c]pyridin-5(4H)-yl)ethanone (Intermediate H, 350 mg, 1.07 mmol) and bis(pinacolato)diboron(542 mg, 2.13 mmol) in dioxane (5.3 mL) was added KOAc (314 mg, 3.20 mmol), (2- dicyclohexylphosphino-2?,4?,6?-triisopropyl- 1,1 ?-biphenyl)[2-(2?-amino- 1,1?- biphenyl)]palladium(II) methanesulfonate (26 mg, 0.032 mmol) and 2-(dicyclohexylphosphino)- 2?,4?,6?-triisopropylbiphenyl (31 mg, 0.064 mmol). The mixture was stirred at 80C for 16 hunder a nitrogen atmosphere. The reaction mixture was cooled to room temperature and 7- bromoisoindolin-1-one (113 mg, 0.533 mmol), K3P04.H20 (313 mg, 1.33 mmol), water (1.3 mL) and (2-dicyclohexylphosphino-2?,4?,6?-triisopropyl- 1,1 ?-biphenyl)[2-(2?-amino- 1,1?- biphenyl)]palladium(II) methanesulfonate (26 mg, 0.032 mmol) were added. The reaction mixture was stirred at 90 C for 4 h under a nitrogen atmosphere. The reaction mixture was thencooled to room temperature and concentrated in vacuo. The crude residue was dissolved indichloromethane (20 mL), dried over anhydrous MgSO4, filtered through celite and concentrated in vacuo. The mixture obtained was purified by silica gel chromatography (MeOH / iPrOAc = 1 10 to 1: 3) to give the title compound (144 mg, 36%) as a white solid. ?H NMR (400 IVIFIz, DMSO-d6, 23 / 24 H) 7.66 – 7.40 (m, 3H), 6.06 – 5.94 (m, 1H), 4.48 (d, J = 9.5 Hz, 2H), 4.62-4.41 (m, 1H),4.18(dd,J36.7, 11.6Hz,2H),3.99-3.77(m,2H),3.59-3.47(m,3H),2.82 (dt, J = 24.3, 5.9 Hz, 2H), 2.43 -2.30 (m, 2H), 2.17-2.06 (m, 3H), 1.93 (d, J = 13.2 Hz, 2H). LCMS M/Z (M+H) 381.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7-Bromo-2,3-dihydro-isoindol-1-one, its application will become more common.

Reference:
Patent; GENENTECH, INC.; CONSTELLATION PHARMACEUTICALS, INC.; CYR, Patrick; BRONNER, Sarah; ROMERO, F. Anthony; MAGNUSON, Steven; TSUI, Vickie Hsiao-Wei; MURRAY, Jeremy M.; WAI, John; LAI, Kwong Wah; WANG, Fei; CHEN, Kevin X.; (351 pag.)WO2017/205538; (2017); A1;,
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Synthetic Route of 923590-95-8, 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. 923590-95-8, name is 4-Bromoisoindoline hydrochloride belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

4-Bromoisoindoleline hydrochloride (174 mg, 0.74 mmol) and triethylamine (158.1 mg, 1.56 mmol) were added to a round bottom flask, DMF was dissolved, and stirred for 10 minutes.The final product 03 (80 mg, 0.25 mmol) was added and stirred at 50 C overnight.The reaction was completed and purified by HPLC to give 100 mg of a colorless oily compound.

The synthetic route of 4-Bromoisoindoline hydrochloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Zhao Yujun; Li Jia; Wang Zengtao; Zhang Shiyan; Zang Yi; Wang Peipei; Sun Dandan; Zhang Hanyan; (155 pag.)CN110818683; (2020); 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., category: indolines-derivatives

A solution of 123 g of pyridinium bromide perbromide in 600 ml of THF was slowly added dropwise to 2-(2-oxopropyl)-1H-isoindole-1,3 (2H)-dione (70 g; 0.345 mol) in 600 ml of THF, and the mixture was then stirred for about 3 h. For workup, the precipitated solids were filtered off, and the mother liquor was concentrated, taken up in ethyl acetate and thoroughly washed with aqueous bisulfite solution. Drying and concentration afforded 150 g of a yellow oil, which was stirred with methyl tert-butyl ether. 63.4 g; m.p.: 142 to 143 C.; ESI-MS [M+H+]=283.95

The synthetic route of 3416-57-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Abbott GmbH & Co. KG; US7105508; (2006); B1;,
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Application of 169037-23-4, 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. 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

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.

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, 5-(Trifluoromethoxy)indoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

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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Synthetic Route of 118289-55-7, 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. 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Example 3. 5-(2-(4-Benzo[d]isothiazol-3-yl)piperazin-1-yl)ethyl)-6-chloro-1,3-dihydro-2H-indol-2-one hydrochloride. (I); A reactor is loaded with 131 g (0.57 mol) of 6-chloro-5-(2-chloroethyl)-1,3-dihydro-indol-2-one, 125 g (0.57 mol) of piperazinyl benzoisothiazole, 260 ml of dimethylsulfoxide, 26 ml of water and 4.3 g (0.0285 mols) ofNaI. The reaction mixture is added with 103 g (0.969 mol) of Na2CO3, with stirring under nitrogen atmosphere. The resulting mixture is heated to about 115-125C in 1 h and kept at said temperature under stirring for approx. 1 hr 45 min, then cooled and slowly added in about 25 min with isopropyl alcohol (650 ml), at a temperature of about 110C, then slowly cooled at 25C. The filtrate and the precipitate are washed with isopropyl alcohol (2 x 130 ml) to obtain 310 g of 5-(2-(4-benzo[d]isothiazol-3-yl)piperazin-1-yl)ethyl)-6-chloro-1,3-dihydro-2H-indol-2-one free base, as a crystalline solid. The resulting product is placed in a 3 L beaker with 1500 ml of purified water, and 150 ml of 32% HCl are dropped therein with stirring. The reaction mixture is kept under stirring for 10 min, filtered, washed with purified water (2 x 500), dried to give 260 g of 5-(2-(4-benzo[d]isothiazol-3-yl)piperazin-1-yl) ethyl)-6-chloro-1,3-dihydro-2H-indol-2-one hydrochloride, as a crystalline solid.

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-Chloro-5-(2-chloroethyl)indolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Dipharma S.p.A.; LUNDBECK PHARMACEUTICALS ITALY S.p.A.; EP1787990; (2007); A2;,
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Adding a certain compound to certain chemical reactions, such as: 20780-72-7, name is 4-Bromoisatin, belongs to indolines-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 20780-72-7, Computed Properties of C8H4BrNO2

General procedure: Indoles (0.20mmol), isatins (0.10mmol), and 60 wtpercentPWA/MCM-41 catalyst (0.0050 g) were stirred in THF(0.3mL) at room temperature for 2.5 h and monitored byTLC. The product were purified by column chromatographyon silica gel using petroleum ether/ethyl acetate (20 : 1, 10 : 1,5 : 1, 2 : 1, 1 : 1) as the eluent. All compounds (3a?3o) werecharacterized by 1H and 13C NMR (400MHz) spectral analysis.The catalyst was separated from the reaction mixture bycentrifugalization, dried at 473K for 4 h after washing withethanol, then continued to be reused for the next reaction.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Xing, Liuzhuang; Hui, YongHai; Yang, Jinghui; Xing, Xuejian; Hou, Yadong; Wu, Yang; Fan, Kui; Wang, Wei; Journal of Chemistry; vol. 2018; (2018);,
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Adding a certain compound to certain chemical reactions, such as: 897957-06-1, name is 6-Bromo-1-methylindolin-2-one, belongs to indolines-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 897957-06-1, Product Details of 897957-06-1

General procedure: General Procedure: Under nitrogen atmosphere, to a stirred solution of N-substituted-2-oxindole (10 mmol) in dry Et2O (40 mL) was added LiHMDS (1.0 M in THF solution, 12 mmol, 12 mL) dropwise at 0 C. The solution was allowed to warm to ambient temperature and stirred for 1 h. Then the solution was cooled to 0 C and TMSCl (13 mmol, 1.6 mL) was added dropwise. The solution was allowed to warm to ambient temperature and stirred for another 3 h. The solvent was removed under reduced pressure, and dry MeCN (40 mL) was charged to the flask. The solution was cooled to 0 C again and Selectfluor (12 mmol, 4.3 g) was added to the solution in small portions. The resulting suspension was allowed to warm to ambient temperature and stirred overnight. The reaction was quenched by the addition of water (20 mL) and EtOAc (20 mL). The reaction mixture was extracted with EtOAc (20 mL ¡Á 2). The combined organic extracts were dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure Purification of the crude product was performed by flash column chromatography (Hexane/EtOAc) to afford 3-fluorooxindole.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Zhao, Jian-bo; Ren, Xinfeng; Zheng, Bu-quan; Ji, Jian; Qiu, Zi-bin; Li, Ya; Journal of Fluorine Chemistry; vol. 215; (2018); p. 44 – 51;,
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Some common heterocyclic compound, 6326-79-0, name is 6-Bromoisatin, molecular formula is C8H4BrNO2, 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 6-Bromoisatin

To R4 (500 mg, 2.21 mmol) in acetonitrile (15 mL) is added Met (0.303 mL, 4.87 mmol) and K2CO3 (1.2 g, 8.68 mmol) and the reaction mixture stirred at 60 C. for 45 min. DCM and water is added and the aqueous layer extracted twice with DCM, the combined organic layers are washed with brine, dried and concentrated. Yield 65%. m/z 240/242 [M+H]+, rt 0.49 min, LC-MS Method b.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6326-79-0, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GRUNDL, Marc; OOST, Thorsten; PAUTSCH, Alexander; PETERS, Stefan; RIETHER, Doris; WIENEN, Wolfgang; US2013/172327; (2013); A1;,
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