Tag: M.W=100-200

These common heterocyclic compound, 16800-68-3, name is 1-Acetylindolin-3-one, 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. Computed Properties of C10H9NO2

To a solution of 1a (35 mg, 0.2 mmol) and 2a (52.4 mg,0.4 mmol) in DCE (3 mL) was added iodine (10 mg, 0.04 mmol). The reaction mixture was heated at 80 C for 24 h, then cooled to room temperature and quenched with saturated sodium thiosulfate. The mixture was extracted with CH2Cl2, the combined organic layer was dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel to afford title compound.

The synthetic route of 1-Acetylindolin-3-one has been constantly updated, and we look forward to future research findings.

Reference:
Article; Guo, Jing; Weng, Jiang; Huang, Gong-Bin; Huang, Lin-Jie; Chan, Albert S.C.; Lu, Gui; Tetrahedron Letters; vol. 57; 49; (2016); p. 5493 – 5496;,
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Reference of 59-48-3, The chemical industry reduces the impact on the environment during synthesis 59-48-3, name is Indolin-2-one, I believe this compound will play a more active role in future production and life.

PREPARATION 11 5-Acetyl-2-oxindole To 95 ml. of carbon disulfide was added 27 g. (0.202 mole) of aluminum chloride, followed by the dropwise addition of a solution of 3 ml. (0.042 mole) of acetyl chloride in 5 ml. of carbon disulfide, with stirring. Stirring was continued for 5 minutes and then 4.4 g. (0.033 mole) of 2-oxindole was added. The resulting mixture was heated under reflux for 4 hours and cooled. The carbon disulfide was removed by decantation and the residue was triturated under water and recovered by filtration. After drying, 3.2 g. of the title compound was obtained, m.p. 225-227 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, Indolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Pfizer Inc.; US4658037; (1987); A;,
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Reference of 100510-65-4, A common heterocyclic compound, 100510-65-4, name is 6-Amino-3,3-dimethylindolin-2-one, molecular formula is C10H12N2O, 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.

b) N-(3,3-Dimethyl-2-oxo-2,3-dihydro-lH-indol-6-yl)-2-methyl-isonicotinamide To a suspension of 2-methylisonicotinic acid (175 mg, 1.28 mmol) in dry toluene (12.8 ml) was added SOCl2 (167 mg, 103 mu, 1.4 mmol) and dry DMF (9.33 mg, 9.89 mu, 128 muetaiotaomicron) under an argon atmosphere. The mixture was heated under reflux for 2 hours and the solvent was evaporated under reduced pressure. The residue was suspended in dry dichloromethane (3.51 ml) and a suspension of 6-amino-3,3-dimethylindolin-2-one (0.15 g, 851 muiotaetaomicron) and DIPEA (330 mg, 446 mu, 2.55 mmol) in dry dichloromethane (5ml) was added portionwise. The suspension was stirred under an argon atmosphere at room temperature for 16 hours, then diluted with dichloromethane, water and 1 M aqueous sodium carbonate solution. The aqueous phase was extracted with dichloromethane. The combined organic layers were washed with 1 M aqueous sodium carbonate solution, dried over sodium sulfate, the solvent was evaporated and the residue purified by silica gel chromatography using dichloromethane/ methanol as eluent. The title compound was obtained as brown solid (99 mg). MS ESI (m z): 296.3 [(M+H)+]. 1H NMR (DMSO-D6, 400 MHz): (ppm) = 10.38 (s, 2H), 8.64-8.62 (m, 1H), 7.71 (m, 1H), 7.64-7.62 (m, 1H), 7.49 (m, 1H), 7.31-7.23 (m, 2H), 2.57 (s, 3H), 1.24 (s, 6H).

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; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BRUNNER, Daniela; MALBERG, Jessica; SHANKAR, Bavani G.; KOLCZEWSKI, Sabine; LIMBERG, Anja; PRINSSEN, Eric; RIEMER, Claus; STOLL, Theodor; WO2014/40969; (2014); A1;,
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Related Products of 110568-64-4, 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. 110568-64-4, name is 6-Nitroisoindolin-1-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 5-nitroisoindolin-l-one (600 mg, 3.37 mmol) in dioxane (30 mL) under a nitrogen atmosphere was added DMAP (616 mg, 5.05 mmol) followed by di-to -butyl dicarbonate (1.16 mL, 5.05 mmol). The resulting reaction mixture was stirred at room temperature overnight, then poured onto water and extracted with EtOAc (3X). The combined organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude residue was purified by chromatography (20% EtOAc in hexanes eluent followed by 20:20:80 DCM: EtOAc: hexane eluent) to provide tot-butyl 5-nitro-l-oxoisoindoline-2-carboxylate (576 mg, 61% yield) as a white solid. NMR (300 MHz, Chloroform-i ) delta 8.43 – 8.35 (m, 2H), 8.10 (d, J = 8.9 Hz, 1H), 4.90 (s, 2H), 1.64 (s, 9H).

The synthetic route of 6-Nitroisoindolin-1-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY OF HAWAII; TURKSON, James; YUE, Peibin; TIUS, Marcus; BROTHERTON-PLEISS, Christine; LOPEZ TAPIA, Francisco, Javier; (420 pag.)WO2018/136935; (2018); A1;,
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Electric Literature of 3676-85-5, These common heterocyclic compound, 3676-85-5, name is 5-Aminoisoindoline-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.

A mixture of the appropriate amine (1 mmol) and the appropriate benzyl bromide (1 mmol) inDMF (0.5 M) was stirred at 60 C until completion of the reaction (up to 40 hours). The reactionmixture was quenched with sat. NaHCO3 and extracted with EtOAc. Crude material was purified by automated flash chromatography (EtOAc:hexanes mixture) to give the desired compound in 12-20% yield; ?H NIVIR (400 MHz,DMSO) 10.81 (s, 1H), 7.64 (d, J= 8.5 Hz, 2H), 7.53 (d, J= 8.5 Hz, 1H), 7.12 (s, 1H), 7.02 (d, J= 2.1 Hz, 1H), 6.95 (dd, J= 8.5, 2.1 Hz, 1H), 4.49 (s, 2H). ?3C NIVIR (101 1VIHz, DMSO) 170.03(s), 169.78 (s), 161.37 (d, J= 250.6 Hz), 154.06 (s), 136.95 (s), 136.83 (s), 135.86 (s), 130.28 (s),125.00 (s), 119.02 (s), 117.02 (s), 116.77 (s), 42.79 (s).

Statistics shows that 5-Aminoisoindoline-1,3-dione is playing an increasingly important role. we look forward to future research findings about 3676-85-5.

Reference:
Patent; THE CENTRE FOR DRUG RESEARCH AND DEVELOPMENT; THE UNIVERSITY OF BRITISH COLUMBIA; ROBERGE, Michel; BARADARAN-HERAVI, Alireza; BALGI, Aruna D.; ZIMMERMANN, Carla D.; KRAUSE, Alexandra; PFEIFER, Thomas Arthur; JAQUITH, James Brian; TAN, Jason Samuel; SHIDMOOSSAVEE, Fahimeh S.; ARNS, Stephen Paul; BAUDELET, Davy Jeremy; (354 pag.)WO2017/49409; (2017); A1;,
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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. Safety of 5-Chloroisoindoline-1,3-dione

General procedure: (0.107) Intermediate 4 (0.001 mol) was dissolved in 15 ml of N ‘N-dimethylformamide solution, anhydrous potassium carbonate (0.00 mol) was added, methyl iodide (0.0015 mol) or benzyl chloride (0.0015 mol)The mixture was stirred at room temperature for 5 hours. The filtrate was distilled off and the solvent was distilled off, and the residue was recrystallized from methanol to give the intermediate compound 17. 17a: near white solid, yield 53.1%

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7147-90-2, its application will become more common.

Reference:
Patent; Shandong University; Zhao Guisen; Liu Yang; Geng Jingkun; Li Yijing; (15 pag.)CN104447496; (2017); B;,
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Reference of 56341-37-8, A common heterocyclic compound, 56341-37-8, name is 6-Chlorooxindole, molecular formula is C8H6ClNO, 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: To the phenstatin-3-aldehyde/isocombretastatin-3-aldehyde(16a-b) (0.303 mmol/0.304 mmol) prepared in the above stepwas added corresponding substituted oxindoles (17a-h)(0.303 mmol) and catalytic amount of piperidine (1.0 ml) in ethanol.Heated the reaction mixture to reflux for 4 h at 85 C. The solidcompounds obtained in the reaction vessel were filtered and washed with ethanol for 4-5 times. After complete air drying thefinal compounds phenstatin/isocombretastatin-oxindole analogs(5a-h and 6a-h) were obtained as pure solids (yield 71-90%).

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, G. Bharath; Nayak, V. Lakshma; Sayeed, Ibrahim Bin; Reddy, Vangala Santhosh; Shaik, Anver Basha; Mahesh, Rasala; Baig, Mirza Feroz; Shareef, Mohd Adil; Ravikumar; Kamal, Ahmed; Bioorganic and Medicinal Chemistry; vol. 24; 8; (2016); p. 1729 – 1740;,
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Application of 7699-18-5, 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. 7699-18-5 name is 5-Methoxyindolin-2-one, 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.

An oven-dried flask was charged with BBr3.SMe2 (2.80 g, 9.20 mmol) and 1,2-dichloroethane (15 mL). 5-Methoxyindolin-2-one (0.3Og, 1.84 mmol) was then added and the mixture was heated to reflux for 18 hours. The reaction was then cooled to room temperature and quenched with MeOH (1.0 mL). The mixture was then extracted into EtOAc washing with brine (3X). The organic layer was dried over MgSO4, filtered and the solvent removed in vacuo; the resulting residue was then purified by column chromatography (silica gel, 94:6 to 92:8, CH2Cl2/Me0H) to give 144 mg, 53 % of a beige powder. MS ESI 149.9 [M + H]+, calcd for [C8H7NO2+ H]+ 150.06

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

Reference:
Patent; UNIVERSITY HEALTH NETWORK; WO2009/79767; (2009); A1;,
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These common heterocyclic compound, 39603-24-2, name is 5,7-Dimethylindoline-2,3-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. Quality Control of 5,7-Dimethylindoline-2,3-dione

General procedure: A mixture of Yb(OTf)3 (0.01 mmol) and ligand L6 (0.02 mmol) wasstirred at r.t. for 2 h in CH2Cl2 (2 mL). The appropriate enones 1 (1mmol) and isatins 2 (0.1 mmol) were then added. The resulting mixturewas stirred at r.t. After the reaction was completed as monitoredby TLC (eluent: hexane-EtOAc, 1:1), the reaction mixture was purifiedby column chromatography (silica gel, eluent: mixture ofhexane and EtOAc).

The synthetic route of 5,7-Dimethylindoline-2,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liu, Lu; Daka, Philias; Sarkisian, Ryan; Deng, Yongming; Wheeler, Kraig; Wang, Hong; Synthesis; vol. 46; 10; (2014); p. 1339 – 1347;,
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Related Products of 15861-30-0, 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 15861-30-0 as follows.

To a solution of indoline-5-carboxylic acid (1 1 .61 mg, 71 .18 gmol) in DCM (0.5 ml_) were added DIPEA (27.60 mg, 213.55 gmol) and HATU (40.60 mg, 106.77 gmol) at 25 C. The mixture was stirred at 25 C for 1 hr and then (2S)-2-amino-4-methylsulfanyl-N-(4-phenylthiazol-2-yl) butanamide (30.0 mg, 71 .1 8 gmol) was added. The reaction mixture was stirred at 25 C for 16 hr. The reaction mixture was concentrated in vacuum to give a residue. The residue was purified through reverse phase-HPLC (FA condition) and followed by prep-TLC (PE/EA=1 /1 ) to afford compound 80 as a white solid. 1 HNMR (400 MHz, MeOD) d = 7.88-7.86 (m, 2H), 7.63-7.59 (m, 2H), 7.39-7.36 (m, 3H), 7.28-7.26 (m, 1 H), 6.58-6.52 (m, 1 H), 4.89-4.86 (m, 1 H), 3.59-3.54 (m, 2H), 3.04-3.00 (m, 2H), 2.68-2.63 (m, 2H), 2.20 – 2.12 (m, 2H), 2.1 1 (s, 3H) ppm. LCMS (ESI) m/z: [M+H]+ = 453.0. Chiral HPLC: Cellucoat-MeOH+ACN(DEA)-40-5min-3mL-35T, 1 .444 min.

According to the analysis of related databases, 15861-30-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; FOGHORN THERAPEUTICS INC.; ANTHONY, Neville, John; MILLAN, David, Simon; VASWANI, Rishi, G.; SCHILLER, Shawn, E.R.; (239 pag.)WO2019/152437; (2019); A1;,
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