Month: March 2021

6941-75-9, name is 5-Bromoisoindoline-1,3-dione, 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. SDS of cas: 6941-75-9

Synthesis of 5-bromo-3-hydroxy-3-(thiophen-3-yl) isoindolin-1-one (3) A solution of 1, 2-dibromoethane (20 ml, 230.35 mmol) in ether/benzene (270 ml/100 ml) was added to a stirred suspension of magnesium turning (8.64 g, 355.6 mmol) in ether (100 ml). The reaction was stirred at room temperature for 2 h. To this was added a solution of n-butyllithium (110 ml, 177.6 mmol) and 3-bromothiophene (2, 29 g, 177.6 mmol) in tetrahydrofuran (200 ml) (prepared at -78 C.) and the reaction was stirred at room temperature for 1 h. Then a solution of 4-bromophthalimide (1, 4 g, 17.7 mmol) in dichloromethane (50 ml) was added and the reaction was stirred at room temperature for 1 h. Progress of the reaction was monitored by TLC. After completion, the reaction mixture was quenched with sat. ammonium chloride and extracted with dichloromethane. The organic layer was separated, dried over sodium sulphate and concentrated under reduced pressure. The residue was purified on combiflash using 25% ethyl acetate in hexane to afford mixture of 5-bromo-3-hydroxy-3-(thiophen-3-yl) isoindolin-1-one (3) as a yellow solid. Yield: 0.97 g, crude; MS (ESI) m/z 307.95 [M-1]-.

The synthetic route of 6941-75-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; eFFECTOR Therapeutics, Inc.; Sprengeler, Paul A.; Reich, Siegfried H.; Ernst, Justin T.; Webber, Stephen E.; Shaghafi, Mike; Murphy, Douglas; Tran, Chinh; (131 pag.)US10112955; (2018); B2;,
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Some common heterocyclic compound, 19727-83-4, name is 6-Nitroindoline, molecular formula is C8H8N2O2, 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: 19727-83-4

Step A 1-Methyl-6-nitroindoline Potassium bis(trimethylsilyl)amide (67 ml of a 0.5M toluene solution) was added slowly to a stirred solution of 6-nitroindoline (5.0 g) in anhydrous tetrahydrofuran (200 ml) at -78 C. under a nitrogen atmosphere. Iodomethane (2.09 ml) was added then the reaction mixture was allowed to warm to room temperature then stirred overnight. Methanol (5 ml) was added then the solution was evaporated to dryness. The residue was dissolved in diethyl ether (300 ml), washed with water, saturated brine then dried (magnesium sulphate) and evaporated to dryness. The crude product was purified by column chromatography on silica using 10% ethyl acetate/petroleum ether (60-80)?30% ethyl acetate/petroleum ether (60-80) and the product crystallized from diethyl ether/petroleum ether (60-80) to afford 0.9 g.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 19727-83-4, its application will become more common.

Reference:
Patent; Merck, Sharp & Dohme, Ltd.; US5696110; (1997); 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. 3485-84-5, name is N-Vinylphthalimide, A new synthetic method of this compound is introduced below., SDS of cas: 3485-84-5

EXAMPLE III-9 tert-Butyl 2-{3-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethenyl]phenoxy}-2-methyl-propanoate In an autoclave, 14.93 g (47.37 mmol) of the compound from Example III-6, 10.25 g (59.21 mmol) of vinylphthalimide, 0.39 g (1.27 mmol) of tris-o-tolylphosphine, 0.07 g (0.32 mmol) [lacuna] and 21.78 g (215.23 mmol) of triethylamine are heated at 130 C. Water/methanol is added, and the precipitate is then filtered off with suction and recrystallized from cyclohexane/ethyl acetate. Yield: 66%. 1H-NMR (200 MHz, CDCl3): delta=1.40 (s, 9H), 1.50 (s, 6H), 6.73 (dd, 1H), 6.86-6.93 (m, 1H), 7.16 (t, 1H), 7.21-7.34 (m, 2H), 7.43 (d, 1H), 7.80-8.00 (m, 4H). MS (DCI/NH3): 425 [M+NH4+].

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; Urbahns, Klaus; Woltering, Michael; Nikolic, Susanne; Pernerstorfer, Josef; Hinzen, Berthold; Dittrich-Wengenroth, Elke; Bischoff, Hilmar; Hirth-Dietrich, Claudia; Lustig, Klemens; US2003/32671; (2003); A1;,
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Application of 7147-90-2,Some common heterocyclic compound, 7147-90-2, name is 5-Chloroisoindoline-1,3-dione, molecular formula is C8H4ClNO2, 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.

30 g (165.2 mmol) of 5-chloroisoindolin-1,3-dione, sodium tertbutoxide 198.2 mmol, methyl iodide 198.2 mmolAnd 200 mL of toluene were mixed, refluxed, heated for 30 minutes, and 1.6 mmol of tetrakistriphenylphosphinepalladium was added thereto, followed by stirring for 3 hours in a reflux state. After the reaction, the reaction solution was returned to room temperature, extracted with water, and the organic layer was recrystallized twice from chloroform and hexane to give 23.9 g of Compound 1-G (yield 74%).

The synthetic route of 7147-90-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LG Chem, Ltd.; SUNGKYUNKWAN University Research & Business Foundation; Yoon Hong-sik; Hong Wan-pyo; Kang Yu-jin; Kim Jin-ju; Han Si-hyeon; (93 pag.)KR2019/101894; (2019); A;,
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Reference of 3339-73-9, 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 3339-73-9 as follows.

General procedure: 1.0 mmol of (1,3-dioxoisoindolin-2-yl) acid, N-ethyl-N-dimethylaminopropylcarbodiimide (EDC) (1.1 mmol), hydroxybenzotriazole(HOBt) (1.2 mmol) and N,N-Diisopropylethylamine (2.0 mmol) weremixed in minimum DMF and the obtained mixture was stirred for5 min. Then, 4-aminoquinoline-diamines (1.0 mmol) was added to thereaction mixture and the stirring was continued for 5 h. The reactionend was proved by thin layer chromatography (TLC). Then, DMF wasevaporated using rotary evaporator and cold water (20 mL) was added,and solid precipitates obtained were filtered and washed with coldwater. The crude product was recrystallized in absolute ethanol.

According to the analysis of related databases, 3339-73-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Rani, Anu; Legac, Jenny; Rosenthal, Philip J.; Kumar, Vipan; Bioorganic Chemistry; vol. 88; (2019);,
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Indoline | C8H9N – PubChem

Electric Literature of 21857-45-4, 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. 21857-45-4, name is 5-Methoxyindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: 4-chloro-2-subsituted quinazoline (1.0 mmol), 5-methoxyindoline or 6-substituted-1,2,3,4-tetrahydroquinoline or 7-methoxy-2,3,4,5-tetrahydro-1H-benzo[b or c]azepine (1.2 mmol) and sodium bicarbonate (3.0 mmol) were added to anhydrous ethanol (5 ml), reacted at room temperature or under refluxing condition for 1-10 h. After the end of reaction, the reactants were poured into ice-water, adjusted pH with 2N hydrochloric acid to 3, extracted with ethyl acetate, dried with anhydrous sodium sulfate. The solvent was removed under vacuum, and the resultant crude product was separated by silica gel column chromatography (eluent: ethyl acetate and petroleum ether for gradient elution, ethyl acetate 5%-80%).; Compound 8 was obtained after reaction at room temperature for 1 h, which was yellow solid, 242 mg, yield 77%, melting point 116-117C. 1H NMR (CDCl3): 6 ppm 2.70 (3H, s, CH3), 3.19 (2H, t, J = 8.0 Hz, 3′-CH2), 3.81 (3H, s, OCH3), 4.45 (2H, t, J = 8.0 Hz, 2′-CH2), 6.69 (1 H, dd, J = 8.8 Hz and 2.4 Hz, ArH-6′), 6.86 (1 H, d, J = 2.4 Hz, ArH-4′), 7.37 (2H, m, ArH-7′ and ArH-6), 7.73 (1 H, t, J = 7.6 Hz, ArH-7), 7.84 (1 H, d, J = 8.4 Hz, ArH-5), 8.03 (1 H, d, J = 8.4 Hz, ArH-8). MS m/z (%) 292 (M+H+, 100).

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

Reference:
Patent; Institute Of Pharmacology And Toxicology Academy Of Militaty Medical Sciences P.L.A.; XIE, Lan; WANG, Xiaofeng; LEE, Kuo-Hsiung; EP2857393; (2015); A1;,
Indoline – Wikipedia,
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Electric Literature of 5332-26-3, A common heterocyclic compound, 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, molecular formula is C9H6BrNO2, 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: The vacuum dried intermediate 3 (0.002 mol) was then reacted with mono- and di-substituted benzoic acids (0.003 mol) separately in presence of anhydrous potassium carbonate (0.003 mol) in DMF (10 mL). The reaction mixture was stirred at room temperature for about 2 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was poured into ice-cold water and allowed stir for 10 min. The solid obtained was filtered and washed successively with distilled water and recrystallized from ethanol to obtain4(a-n).

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; Kumar, C.S. Chidan; Loh, Wan-Sin; Chandraju, Siddegowda; Win, Yip-Foo; Tan, Weng Kang; Quah, Ching Kheng; Fun, Hoong-Kun; PLoS ONE; vol. 10; 3; (2015);,
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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. 20870-79-5, name is 5-Nitroindolin-2-one, A new synthetic method of this compound is introduced below., SDS of cas: 20870-79-5

General procedure: To the 3-subtitutedphenyl-1H-pyrazole-5-carbaldehydes 11(a-d) prepared in the above step was added corresponding substituted oxindoles and catalytic amount of piperdine (1.0ml) in ethanol. Heated the reaction mixture to reflux for 4h at 85C. The solid compounds obtained in the reaction vessel were filtered and washed with ethanol for 4-5 times. After complete air drying the final compounds (Z)-3-((3-phenyl-1H-pyrazol-5-yl)methylene)indolin-2-one analogs 12(a-u) were obtained as pure solids (yield 75-80%).

The synthetic route of 20870-79-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kamal, Ahmed; Shaik, Anver Basha; Jain, Nishant; Kishor, Chandan; Nagabhushana, Ananthamurthy; Supriya, Bhukya; Bharath Kumar; Chourasiya, Sumit S.; Suresh, Yerramsetty; Mishra, Rakesh K.; Addlagatta, Anthony; European Journal of Medicinal Chemistry; vol. 92; (2015); p. 501 – 513;,
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Synthetic Route of 201940-08-1, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 201940-08-1 name is tert-Butyl 5-bromoisoindoline-2-carboxylate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Commercially available tert-butyl 5-bromoisoindoline-2-carboxylate (i.e., Matric Scientific, catalog 74109) (20 g, 0.0671 mol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(l,3,2- dioxaborolane) (17 g, 0.0671 mol), KAc (8.5 g, 0.087 mol) and PdCfedppf (1.8 g, 0.00221 mol) in 200 mL 1,4-dioxane was heated to 80C overnight. The mixture was cooled, water was added, the mixture was extacted with EA, dried and concentrated. The residue was purified by chromatography on silica gel to afford the title compound. 1HNMR (300MHz,DMSO)5: 1.2-1.3 (s, 12H), 1.4-1.5 (s, 9H), 4.5-4.6 (s, 4H), 7.2-7.3(m,lH), 7.5-7.6 (M,2H); LC-MS: m/z=246 (M+l-100)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl 5-bromoisoindoline-2-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MANDAL, Mihir; TANG, Haifeng; XIAO, Li; SU, Jing; LI, Guoqing; YANG, Shu-Wei; PAN, Weidong; TANG, Haiqun; DEJESUS, Reynalda; HICKS, Jacqueline; LOMBARDO, Matthew; CHU, Hong; HAGMANN, William; PASTERNAK, Alex; GU, Xin; JIANG, Jinlong; DONG, Shuzhi; DING, Fa-Xiang; LONDON, Clare; BISWAS, Dipshikha; YOUNG, Katherine; HUNTER, David, N.; ZHAO, Zhiqiang; YANG, Dexi; WO2015/112441; (2015); A1;,
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Related Products of 20870-90-0, The chemical industry reduces the impact on the environment during synthesis 20870-90-0, name is 5-Bromo-1-methyl-2-oxoindoline, I believe this compound will play a more active role in future production and life.

General procedure: To a precooled stirring suspension of NaH (6.0 mmol, 0.144 g) in THF (10 mL) at -78 C was added a solution of N-methyloxindole (5a) (6.0 mmol, 0.883 g) in THF (10 mL) dropwise. Then the cooling bath was removed and stirring continued for 5 min (till the formation of clear solution). Then the reaction mixture was again cooled to -78 C and a solution of methyl 3-hydroxy-2-methylene-3-phenylpropanoate (6a) (2.0 mmol, 0.468 g) in THF (15 mL) was added dropwise over 30 min. After stirring for further 10 min at the same temperature, the cooling bath was removed and the reaction was quenched with saturated NH4Cl solution and extracted with EtOAc (3¡Á30 mL). Combined organic layer was dried over anhydrous Na2SO4.. Solvent was removed and the crude obtained was purified by column chromatography(10-15% EtOAc in hexanes) provided title compound (7a) (0.539 g) as a colorless solid in 84% yield.

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-methyl-2-oxoindoline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Basavaiah, Deevi; Lingam, Harathi; Babu, Thelagathoti Hari; Tetrahedron; vol. 74; 19; (2018); p. 2306 – 2313;,
Indoline – Wikipedia,
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