Tag: M.W=200-300

A common compound: 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-one, belongs to indolines-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 118289-55-7

10. Preparation of ziprasidone in toluene In a 250 ml three necked flask was charged BITP HCl (5g), Na2C03 (6. 5g), CEI (5g), NaI (1. 5g) and toluene (30ml) ; the mixture was heated at reflux for 22.5 hours. After cooling to the room temperature the reaction product was filtrated, washed with methanol and triturated in water. After drying the product weights 7.27g (yield 86%, purity by HPLC 98.3%).

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, 118289-55-7, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TEVA PHARMACEUTICAL INDUSTRIES LTD.; TEVA PHARMACEUTICALS USA, INC.; WO2005/40160; (2005); A2;,
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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. 20870-78-4, name is 5-Bromoindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. 20870-78-4

To a stirred solution of 5-bromoindolin-2-one (LIV, 7.25 g, 34.36 mmol) in tetrahydrofuran (70 mL) under nitrogen atmosphere, was added sodium hydride (5.9 g, 137.0 mmol) portion-wise at 0 C. After addition of sodium hydride, the reaction was stirred at room temperature for 30 min, then cooledto 0 C. methyl iodide (8.5 mL, 137.0 mmol) was added, and then allowed to stir at room temperature for 2h. The reaction mass was cooled to 0 C and carefully quenched with ice-water. Then the reaction mixture was diluted with water (150 mL) and ethylacetate (150 mL). The organic layer was separated, washed with water, brine solution, dried over sodium sulphate and concentrated under reduced pressure to afford the titled product as brown colour solid (LV, 7.4 g, 85%). LC-MS m/z calcd for CnHi2BrNO, 253.0; found 254.0 [M+H]+.

The synthetic route of 20870-78-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JUBILANT BIOSYS LIMITED; RAJAGOPAL, Sridharan; HALLUR, Mahanandeesha S.; DEWANG, Purushottam; MURUGAN, Kannan; KUMAR C.H., Durga Prasanna; IYER, Pravin; MULAKALA, Chandrika; SIVANANDHAN, Dhanalakshmi; NAIR, Sreekala; ZAINUDDIN, Mohd.; TANTRY, Subramanyam Janardhan; GAJENDRAN, Chandru; RAJAGOPAL, Sriram; (334 pag.)WO2017/195216; (2017); A1;,
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2058-72-2, A common compound: 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, belongs to indolines-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

General procedure: A solution of isatin (0.035 mmol, 1.2 equiv), tryptamine (0.03 mmol, 1.0 equiv) and (R)-3,3′-bis(9-anthracenyl)-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate (0.006 mmol, 0.2 equiv) was prepared in dry CH2Cl2 (0.06 M) at 25 C in an oven-dried and Ar-purged 4 mL vial fitted with a magnetic stir bar. The reaction was stirred until it was complete as judged by TLC (80% EtOAc/hexanes). The reaction was then concentrated and loaded onto a flash silica gel column (gradient of EtOAc/hexanes ending in 80% EtOAc/hexanes) to afford the spiroindolone product.

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-Bromo-1-methylindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Badillo, Joseph J.; Silva-Garcia, Abel; Shupe, Benjamin H.; Fettinger, James C.; Franz, Annaliese K.; Tetrahedron Letters; vol. 52; 43; (2011); p. 5550 – 5553;,
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675109-26-9, name is 6-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. 675109-26-9

To a solution of 6-bromoisoindolin-l-one (2.418 g, 11.4 mmol) in DMF (57 mL) at 0 C. was added NaH (0.547 g, 13.68 mmol). The resulting dark suspension was allowed to stir for 60 min before addition of PMBC1 (1.86 mL, 13.68 mmol). The reaction was then allowed to stir at room temperature for 3 hours. The crude was diluted by EtOAc, washed with water and brine. The organic layers were dried over Na2SO4 and concentrated. The residue was purified by chromatography on silica gel using 0->50% EtOAc in hexanes to afford 3.18 g yellow solid as compound 2 (84% yield). 1H NMR (400 MHz, Chloroform-d) delta8.04 (d, J=1.9 Hz, 1H), 7.65 (dd, J=8.0, 1.9 Hz, 1H), 7.25 (d, J=8.6 Hz, 2H), 6.89 (d, J=8.6 Hz, 2H), 4.75 (s, 2H), 4.22 (s, 2H), 3.82 (s, 3H).

Statistics shows that 675109-26-9 is playing an increasingly important role. we look forward to future research findings about 6-Bromoisoindolin-1-one.

Reference:
Patent; ENANTA PHARMACEUTICALS, INC.; Wang, Guoqiang; He, Jing; Wang, Bin; Shen, Ruichao; Granger, Brett; Or, Yat Sun; US2019/62310; (2019); A1;,
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2058-72-2, The chemical industry reduces the impact on the environment during synthesis 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, I believe this compound will play a more active role in future production and life.

General procedure: To a flame-dried screw-capped test tube equipped with a magnetic stir bar was added 1, 4, 7, 10, 13, 16-hexaoxacyclooctadecane (0.396 g, 1.5 mmol), KF (0.087 g, 1.5 mmol) and 1- methylindoline-2,3-dione 3 (0.50 mmol). Then the screw-capped tube was evacuated and backfilled with argon. The mixture was dissolved in THF (2.0 mL) under argon atmosphere. The resultant reaction mixture was kept stirring at 30 C for 5 min. To the stirring solution was then added isoquinoline 1 (0.50 mmol) and the aryne precursor 2 (0.75 mmol). Then the reaction mixture was placed in preheated oil bath at 70 C. When TLC control showed the completion of the reaction (typically after 24 h), the reaction mixture cooled to room temperature and the solvent was evaporated and the crude residue was subsequently purified by flash column chromatography on silica gel to afford the corresponding spirooxazino isoquinoline derivatives (4) as an inseparable mixture of diastereomers in moderate to good yields. The dr was determined by 1H MR analysis of crude reaction mixture

The chemical industry reduces the impact on the environment during synthesis 5-Bromo-1-methylindoline-2,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Patent; COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH; THANKAPPAN, Biju Akkattu; BHUNIA, Anup; ROY, Tony; WO2014/184808; (2014); A1;,
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2436-29-5, 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. 2436-29-5, name is 3-(1,3-Dioxoisoindolin-2-yl)propanal belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Intermediate 62 : 2-f3-f4-Methyl-3-oxopiperazin-l-vnpropynisoindoline-l,3- dione (0595) To a mixture of 3-(l,3-dioxoisoindolin-2-yl)propanal (515 mg, 2.53 mmol, commercially available from Fluorochem) and Na(OAc)3BH (815.9 mg, 3.85 mmol) in 2-MeTHF (20 mL) was added l-methylpiperazin-2-one (0.420 mL, 3.82 mmol, commercially available from Fluorochem). The mixture was stirred at rt for 4 h 45 min. To the reaction mixture was added aqueous 2M Na2C03 (10 mL) and this mixture stirred at rt for 10 min giving an aqueous phase at approximately pH 10. The layers were separated and the aqueous layer washed with EtOAc (2 x 10 mL). The organic layers were filtered through a cartridge fitted with a hydrophobic frit and the filtrate evaporated in vacuo to give a pale yellow crystalline solid. 2-(3-(4-methyl-3-oxopiperazin-l-yl)propyl)isoindoline-l,3-dione (660.5 mg, 2.192 mmol, 86 % yield). (0596) LCMS (2 min high pH); Rt = 0.74 min, m/z = 302 for [MH]+

The synthetic route of 2436-29-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; ATKINSON, Stephen John; DEMONT, Emmanuel Hubert; HARRISON, Lee Andrew; LEVERNIER, Etienne; PRESTON, Alexander G; SEAL, Jonathan Thomas; WALL, Ian David; WATSON, Robert J; WOOLVEN, James Michael; (225 pag.)WO2017/174621; (2017); 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. 6326-79-0, name is 6-Bromoisatin belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. 6326-79-0

To a solution of 6-bromorsatin (CASNo. 6326-79-0, 4 52 g, 20 0 mmol) in acetonrtrile (150 mL) was added potassium carbonate (11 1 g, 80 mmol) followed by iodomethane (2 75 mL, 44 0 mmol) The reactron was then placed at 60 C and stirred for 40 minutes The reaction was then cooled to room temperature, tittered and concentrated to 10% of the original volume The reaction was then diluted with dichloromethane, water and brine The layers were separated and the aqueous layer was extracted two additional times with dichloromethane. The organic extracts were combined, dried over anhydrous sodium sulfate filtered and concentrated to provide 6-bromo-1-methyl-1 H-iotandole-2,3- dione as an orange solid without the need for further punfication The beta-bromo-1-methyl- 1 H-iotandole-2,3-diotaone (1 0 g, 4 2 mmol) was then treated with hydrazine hydrate (7 0 mL, 225 mmol) The reaction was heated to 130 C and stirred for 80 minutes, at which time the reaction was placed at room temperature and cooled by the addition of ice Once the reaction was cooled to room temperature it was diluted with dichloromethane and water and the layers were separated The aqueous layer was extracted an additional two times with dichloromethane, and the organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated The resulting residue was purified by silica gel flash chromatography (ethanol-dichloromethane 0 to 2%) to afford 6-bromo- 1-methyl-1 ,3-diotahydro-mdol-2-one, MS (ES+) m/z 225 9 (IvH-H)*

The synthetic route of 6326-79-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; ADAMS, Christopher Michael; CHAMOIN, Sylvie; HU, Qi-Ying; ZHANG, Chun; WO2010/130794; (2010); A1;,
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These common heterocyclic compound, 15362-40-0, name is 1-(2,6-Dichlorophenyl)-2-indolinone, 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. 15362-40-0

General procedure: A finely ground mixture of 5-substituted indole-3-carboxaldehyde (1 mmol) and active methylene compound (indolinone/oxindole/barbituric acid/1-(3-chlorophenyl)-3-methyl-2-pyrazolin-5-one)/2-trifluoromethylbenzaldehyde (1.2 mmol) was irradiated in microwave oven for 1-5 min. The solid product was washed with diethyl ether and purified by column chromatography to get pure products 2-5 and 11-28 except compound 3. Compound 3 was prepared by treatment of 5-substituted indole-3-carboxaldehyde with indolinone in ethanol-water in presence of NaOH (1.5 mmol).

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 15362-40-0.

Reference:
Article; Shaveta; Singh, Palwinder; European Journal of Medicinal Chemistry; vol. 74; (2014); p. 440 – 450;,
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20870-78-4,Some common heterocyclic compound, 20870-78-4, name is 5-Bromoindolin-2-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.

Under argon, 2.64 g (66 mmol) of sodium hydride (60% in mineral oil) were suspended in 25 ml of THF and cooled to 0 C. A solution of 4.00 g (18.86 mmol) of 5-bromo-1,3-dihydro-2H-indol-2-one in 25 ml of DMF was added dropwise and the mixture was stirred at 0 C. for 30 min. Subsequently, 4.11 ml (66 mmol) of methyl iodide were slowly added dropwise thereto, then the reaction mixture was warmed to RT and stirring continued at this temperature overnight. For workup, the mixture was poured onto 200 ml of 1M hydrochloric acid and extracted three times with ethyl acetate. The combined organic phases were washed with water, then a saturated sodium chloride solution, dried over sodium sulphate and concentrated on a rotary evaporator. The residue was dissolved in 200 ml of acetonitrile and the mineral oil was extracted with n-pentane. The acetonitrile phase removed was concentrated on a rotary evaporator and the remaining brownish solid was dried under HV. This gave 4.45 g (84% of theory) of the title compound in 91% purity. LC-MS (Method 3): Rt=1.18 min; m/z=254, 256 (M+H)+. 1H NMR (400 MHz, DMSO-d6): delta [ppm]=1.27 (s, 6H), 3.12 (s, 3H), 6.99 (d, 1H), 7.45 (dd, 1H), 7.60 (d, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromoindolin-2-one, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; Fuerstner, Chantal; Ackerstaff, Jens; Straub, Alexander; Meier, Heinrich; Tinel, Hanna; Zimmermann, Katja; Tersteegen, Adrian; Zubov, Dmitry; Kast, Raimund; Schamberger, Jens; Schaefer, Martina; Boerngen, Kirsten; US2015/148340; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 20870-78-4, name is 5-Bromoindolin-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 20870-78-4, 20870-78-4

A. 5-(4,4,5,5-Tetramethyl-l ,3>2-dioxaborolan-2-yl)indolin-2-one. Bis(pinacolato)diboron (1.31 g, 4.71 mmol), dichloro[l,l’-bis(diphenylphosphino) ferrocenejpalladium (II) dichloro-methane (385 mg, 0.47 mmol) and potassium acetate (1.38 g, 14.1 mmol) were successively added to a solution of 5-bromooxindole (1.0 g, 4.71 mmol) in methylene chloride (25 mL), followed by DMSO (15 mL). The crude mixture was diluted with water, extracted with methylene chloride (3x). the combined organic fractions were washed with water, brine, dried over magnesium sulfate, filtered, and the volatiles were removed under reduced pressure. The crude product was triturated with diethyl ether, sonicated, and the precipitate was collected by filtration to afford the title compound (165 mg, 14%). MS (ESI) m/z 260.3 [M+l]+.

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-Bromoindolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SIGNAL PHARMACEUTICALS, LLC; WO2008/51493; (2008); A2;,
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