Month: July 2021

Some common heterocyclic compound, 4702-13-0, name is N-Phthaloylglycine, molecular formula is C10H7NO4, 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 N-phthaloylglycine (36.3 mg, 0.177 mmol) in CH2Cl2 (1.8 mL) were added(COCl)2 (46 L, 0.532 mmol) and DMF (1 drop) at 0 C. The reaction mixture was stirred at0 C for 10 min and at room temperature for 2 h. The solvents were removed under reduced pressure. Azeotropic distillations were carried out with toluene (2 × 2 mL) under reducedpressure. The residue (acid chloride) was used for next step without further purification.To a solution of compound 5 (25.0 mg, 0.0592 mmol) and pyridine (43 L, 0.532 mmol) inCH2Cl2 (0.3 mL) was added a solution of the above crude product (acid chloride) in CH2Cl2 (0.6mL) at 0 C. The reaction mixture was stirred at 0 C for 30 min and at room temperature for 9 h.After cooling to 0 C, the reaction mixture was quenched by addition of saturated NaHCO3 aq.(5 mL). The whole mixture was extracted with CH2Cl2 (2 10 mL), and the combined organiclayers were dried with Na2SO4. After filtration and evaporation, the crude was purified by silicagel chromatography (n-hexane/EtOAc 1:1 to 1:2) to give compound 14 as a pale yellow oil (34.0mg, 94%)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4702-13-0, its application will become more common.

Reference:
Article; Natori, Yoshihiro; Hwang, Candy S.; Lin, Lucy; Smith, Lauren C.; Zhou, Bin; Janda, Kim D.; Beilstein Journal of Organic Chemistry; vol. 15; (2019); p. 1020 – 1031;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 32692-19-6, name is 5-Nitroindoline, A new synthetic method of this compound is introduced below., Application In Synthesis of 5-Nitroindoline

Example 13; 3-[1-(1H-benzimidazol-2-yl)-2,3-dihydro-1H-indol-5-yl]-1-ethyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one 13a) tert-butyl 5-nitro-2,3-dihydro-1H-indole-1-carboxylate To a stirred mixture of 5-nitroindoline (5.0 g) and Boc2O (7.07 mL) in THF (100 mL) was added DMAP (0.5 g) at room temperature. The mixture was stirred at 60 C. for 3 h. The mixture was quenched with water, treated with sat. NaHCO3aq. and extracted with EtOAc. The organic layer was dried over MgSO4 and concentrated in vacuo. The residue was used for the next reaction without further purification.

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; TANIGUCHI, Takahiko; YOSHIKAWA, Masato; MIURA, Kasei; HASUI, Tomoaki; HONDA, Eiji; IMAMURA, Keisuke; KAMATA, Makoto; KAMISAKI, Haruhi; QUINN, John F.; RAKER, Joseph; CAMARA, Fatoumata; WANG, Yi; US2011/319394; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 1127-59-9, A common heterocyclic compound, 1127-59-9, name is 7-Methylindoline-2,3-dione, molecular formula is C9H7NO2, 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: A suspension mixture of N-(2,3,4,6-tetra-O-acetyl-beta-d-glucopyranosyl)thiosemicarbazide 2 (2mmol, 0.84g) and appropriate substituted isatin 3a-l (2mmol) and glacial acetic acid (0.02mL) in absolute ethanol was microwave irradiated for 5?15min (depending on substituents on benzene ring of isatins). After irradiating for 1?3min, the suspension mixture became a clear solution. The irradiation was continued in a given time. At the end of reaction process, the precipitate appeared. Upon completion, monitored by TLC, the reaction mixture was cooled to room temperature; the color precipitate was filtered with suction. The crude product was recrystallized from 96percent ethanol or mixture of toluene-96percent ethanol (2:1 in volume) to afford the title compounds of substituted isatin N-(2,3,4,6-tetra-O-acetyl-beta-d-glucopyranosyl) thiosemicarbazones 4a-l. The spectral (FT-IR, 1H NMR, 13C NMR and ESI-MS or EI-HRMS) data are in good agreement with their structures.

The synthetic route of 1127-59-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Thanh, Nguyen Dinh; Giang, Nguyen Thi Kim; Quyen, Tran Ha; Huong, Doan Thi; Toan, Vu Ngoc; European Journal of Medicinal Chemistry; vol. 123; (2016); p. 532 – 543;,
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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. 603-62-3, name is 3-Nitrophthalimide, A new synthetic method of this compound is introduced below., category: indolines-derivatives

General procedure: A mixture of the appropriate thiol (6 mmol), 3-nitrophthalimide(4 mmol) and K2CO3 (10 mmol) in 20 mL acetone was heated underreflux for 24 h. The reaction was cooled to room temperature anddiluted with 150 mL water. The mixture was subsequently acidifiedto pH 2 with 6 N HCl. The resulting precipitate was collectedby filtration and dried at 50 C [19].

The synthetic route of 603-62-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Van Der Walt, Mietha M.; Terre’Blanche, Gisella; Petzer, Anel; Petzer, Jacobus P.; Bioorganic Chemistry; vol. 59; (2015); p. 117 – 123;,
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Indoline | C8H9N – PubChem

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. 13220-46-7, name is 4-Methylindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C9H9NO

5-Iodo-4-methyl-2-oxindole To 2 g of 4-methyl-2-oxindole in 40 mL of glacial acetic acid in an ice bath was added 3.67 g N-iodosuccinimide. The mixture was stirred for 1 hour, diluted with 100 mL 50% acetic acid in water and filtered. The resulting white solid was dried under high vacuum to give 3.27 g (88% yield) of the title compound as an off white solid.

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 13220-46-7.

Reference:
Patent; Sugen, Inc.; US6878733; (2005); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. Application In Synthesis of 1-Acetylindolin-3-one

General procedure: 1a (35.0 mg, 0.2 mmol, 1 equiv.), tert-BuOK (22.4 mg, 0.2 mmol, 1.0 equiv.) were added to a Schlenk tube. Then 2 ml THF was added using a syringe. The reaction mixture was stirred 15min,and then added iodonium salt 2 (0.2 mmol, 1.0 eq). The reaction was stirred at 30C for 10 hours.After cooling to room temperature, the solvent was removed in vacuo and the residue was purifiedby silica gel using a proper eluent (EtOAc/Hexane) to afford the desired products

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

Reference:
Article; Zhang, Yanxia; Han, Jianwei; Liu, Zhen-Jiang; Synlett; vol. 26; 18; (2015); p. 2593 – 2597;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 74572-29-5, name is 5-Chloroisoindolin-1-one, A new synthetic method of this compound is introduced below., Product Details of 74572-29-5

In a 25 mL sealed tube, 5-chloro-2,3-dihydro-isoindol-1-one (80.1 mg, 4.8 mmol), 4-bromo-6,7-dihydro-5H-[2]pyrindin-7-ylamine (intermediate B-18 [C], 937 mg, 4.4 mmol), CuI (200 mg, 1.1 mmol), Cs2CO3 (3.0 g, 9.2 mmol) and (+)-(S,S)-1,2-diaminocyclohexane (0.4 mL, 3.2 mmol) were dissolved in dioxane (16 mL). The resulting reaction mixture was heated at 150 C. for 3 hours before it was poured into H2O (50 mL) and extracted with EtOAc (2×125 mL). The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give a crude product which was purified by silica gel flash chromatography (30-100% EtOAc-hexane gradient) to yield the title compound (1.02 g, 80%) as a light yellow solid. MS: 300.2 (M+H+).

The synthetic route of 74572-29-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hoffmann-La Roche Inc.; Aebi, Johannes; Amrein, Kurt; Chen, Wenming; Hornsperger, Benoit; Kuhn, Bernd; Liu, Yongfu; Maerki, Hans P.; Mayweg, Alexander V.; Mohr, Peter; Tan, Xuefei; Wang, Zhanguo; Zhou, Mingwei; US2013/143863; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 32692-19-6, name is 5-Nitroindoline, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C8H8N2O2

Example VII; tert-butyl 5-nitro-2,3-dihydro-indole-1 -carboxylate5 g 5-nitro-2,3-dihydro-1 H-indole are dissolved in 70 ml acetonitrile. 7.3 g di- tert-butyl-dicarbonate and 900 mg 4-dimethylaminopyridine are added. After stirring for 24 hours at ambient temperature the mixture is divided between 1 N HCI and ethyl acetate. The aqueous phase is extracted with ethyl acetate and the combined organic phases are washed with saturated sodium hydrogen carbonate solution and saturated sodium chloride solution. After drying with magnesium sulphate the solvents are eliminated in vacuo. The residue is extracted from diisopropylether/petroleum ether. Yield: 6.6 g (82 % of theory) Mass spectrum (ESI+): m/z = 265 [M+H]+

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 32692-19-6.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; WO2009/16119; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Oxoindoline-5-carboxylic Acid

General procedure: Compound 7 (2.1 g, 0.012 mol) and HBTU (5.0 g, 0.013 mol) were dissolved in dry DMF, in a 250 ml round bottom flask. DIPEA (6.5 ml, 0.037 mol) was added and the reaction mixtures were stirred for 30 min. L or D- phenylalanine methyl ester hydrochloride (3.0 g, 0.014 mol) or glutamic acid dimethyl ester hydrochloride (3.0 g 0.014 mol) was added and the reaction mixture was kept stirring overnight under ambient conditions. Reaction monitoring by TLC was performed on silica gel plates using CHCl3:MeOH 9:1 as eluent. Saturated NaHCO3 solution (150 ml) was added to the mixture and the precipitate was filtered, washed with saturated NaHCO3 solution and water. The crude product was purified by column chromatography CHCl3:MeOH (95:5) to give the product as white to off-white solid.

The synthetic route of 102359-00-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nemes, Zoltan; Takacs-Novak, Krisztina; Voelgyi, Gergely; Valko, Klara; Beni, Szabolcs; Horvath, Zoltan; Szokol, Balint; Breza, Nora; Dobos, Judit; Szantai-Kis, Csaba; Illyes, Eszter; Boros, Sandor; Kok, Robbert Jan; ?rfi, Laszlo; Bioorganic and Medicinal Chemistry Letters; vol. 28; 14; (2018); p. 2391 – 2398;,
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Indoline | C8H9N – PubChem

Application of 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: The reactions are conducted in a custom made, twelve membered carousal containing glass reaction chambered of 20 ml volume. To the stirred solution of 6-methylfuro[3,4-c]pyridine-3,4(1H,5H)-dione(200 mg, mmole) (1 equivalence) in ethanol (10 ml) , piperidine/pyrrolidine(1 equivalence) was added. To the stirring solution appropriateisatins (1.1 equivalence) were added under nitrogen atmosphere and the resulting reaction mixture was refluxed at 80 C for 14 h (within which substantial amount of product precipitates from the reaction mixture). Then reaction mixture was cooled to room temperature and solvent was syringed off and the solid was washed with ethanol(2×5 ml) and dried in a Genevac to give desired 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; Luthra, Tania; Naga Lalitha; Uma; Sen, Subhabrata; Bioorganic and Medicinal Chemistry; vol. 26; 18; (2018); p. 4996 – 5005;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem