Tag: M.W=100-200

Electric Literature of 39755-95-8, A common heterocyclic compound, 39755-95-8, name is 5-Methoxyisatin, molecular formula is C9H7NO3, 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.

The mixture was poured into 500 g of ice and extracted 3 times with ethyl acetate. The combined extracts were dried over anhydrous sodium sulfate and concentrated to give 5.1 g (65% yield) of 5-methoxyisatin as a dark red solid. 5-Methoxyisatin (5.0 g) and 30 mL of hydrazine hydrate were heated to reflux for 15 minutes. The reaction mixture was cooled to room temperature and 50 mL of water was added. The mixture was extracted 3 times with 25 mL of ethyl acetate each time, the organic layers combined, dried over anhydrous sodium sulfate and concentrated to give a yellow solid. The solid was stirred in ethyl acetate and 1.1 g of insoluble material was removed by vacuum filtration and saved. This material proved to be 2-hydrazinocarbonylmethyl-4-anisidine. The filtrate was concentrated and chromatographed on silica gel eluding with ethyl acetate:hexane (1:1) to give 0.7 g of 5-methoxy-2-oxindole as a yellow solid.

The synthetic route of 39755-95-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUGEN, Inc.; US2003/69421; (2003); A1;; ; Patent; Sugen, Inc.; US6051593; (2000); A;,
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Related Products of 550-44-7, These common heterocyclic compound, 550-44-7, name is 2-Methylisoindoline-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.

Prepared according to a literature procedure (Beilstein I Org. Chem., 2012, 8, 192-200). N-Methylphthalimide (5 g, 30.4 mmol) was dissolved in MeOH (85 mL) andTHF (175 mL), then cooled to 0C. Sodium borohydride (1.15 g, 30 mmol) was added portionwise over 10 minutes, then the reaction mixture was stirred at 0C for a further 30 minutes. The reaction mixture was quenched with water and extracted with EtOAc, then the organic layers were dried over sodium sulphate and concentrated under reduced pressure, to afford the title compound (3.64 g, 73%) as a white solid.

The synthetic route of 550-44-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UCB BIOPHARMA SPRL; BROWN, Julien Alistair; CALMIANO, Mark Daniel; JONES, Elizabeth Pearl; KROEPLIEN, Boris; REUBERSON, James Thomas; SELBY, Matthew Duncan; SHAW, Michael Alan; ZHU, Zhaoning; WO2015/86512; (2015); A1;,
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Application of 675109-45-2, A common heterocyclic compound, 675109-45-2, name is 6-Amino-2,3-dihydro-1H-isoindol-1-one, molecular formula is C8H8N2O, 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.

Example 1: methyl 3-((R)-l-((R)-2-(3,4-dimethoxyphenyl)-2-(3-oxoisoindolin-5- ylamino)acetyl)pyrrolidin-2-yl)-4-(isopropylsulfonyl)phenylcarbamate; [00212] A solution of Intermediate 6 (300 mg, 2.0 mmol), 3,4- dimethoxyphenylboronic acid (370 mg, 2.0 mmol) and glyoxylic acid monohydrate (224 mg, 2.4 mmol) in acetonitrile/ DMF (4 mL, 4: 1) was heated in the microwave at 100 0C for 10 min. The reaction mixture was concentrated in vacuo and purified by flash chromatography (0% to 20% MeOH in CH2Cl2) to yield IA (600 mg, 87%) as a yellow solid. MS (ESI) m/z 343.2 (M+H)+.

The synthetic route of 675109-45-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2008/79759; (2008); A1;,
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Related Products of 7699-18-5, 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 7699-18-5 as follows.

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%).

According to the analysis of related databases, 7699-18-5, the application of this compound in the production field has become more and more popular.

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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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 60434-13-1 as follows. SDS of cas: 60434-13-1

General procedure: To a flame-dried screw-capped test tube equipped with a magnetic stir bar was added I, 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 added pyridine 7 (0.75 mmol) and the aryne precursor 2 (0.75 mmol). When TLC control showed the completion of the reaction (typically after 12 h), the reaction stopped and the crude reaction mixture was purified by column chromatography on silica gel to afford the corresponding indolin 2-one derivatives 8 in good yields.

According to the analysis of related databases, 60434-13-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH; THANKAPPAN, Biju Akkattu; BHUNIA, Anup; ROY, Tony; WO2014/184808; (2014); A1;,
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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. 334952-09-9, name is 2-Oxoindoline-6-carboxylic acid, A new synthetic method of this compound is introduced below., name: 2-Oxoindoline-6-carboxylic acid

Example 31 COMPOUND IN-023 2-Oxo-3-[5-(2-pyrrolidin-1-yl-ethoxy)-1H-indol-2-ylmethylene]-2,3-dihydro-1H-indole-6-carboxylic acid 2-Oxo-2,3-dihydro-1H-indole-6-carboxylic acid was condensed with 5-(2-pyrrolidin-1-yl-ethoxy)-1H-indole-2-carbaldehyde to give the title compound. 1H-NMR (360 MHz, DMSO-d6) delta 12.86 (s, 1H, NH), 11.11 (br s, 1H, NH), 8.01 (s, 1H, H-vinyl), 7.78 (d, J=8 Hz, 1H), 7.64 (dd, J=1.5 & 8 Hz, 1H), 7.51 (d, J=9 Hz, 1H), 7.43 (d, 1H), 7.15 (d, J=2 Hz, 1H), 7.10 (s, 1H), 4.11 (t, J=6 Hz, 2H, CH2), 2.89 (t, J=6 Hz, 2H, CH2), 2.61 (m, 4H, 2*CH2), 1.71 (m, 4H, 2*CH2). MS-Ve APC1 m/z 416.5 [M+-1].

The synthetic route of 334952-09-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tang, Peng Cho; Harris, G. Davis; Li, Xiaoyuan; US2002/52369; (2002); A1;,
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Some common heterocyclic compound, 59-48-3, name is Indolin-2-one, molecular formula is C8H7NO, 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 Indolin-2-one

An oven-dried 250 mL round-bottom flask containing indolin-2-one (5.00 g, 36.7 mmol) was fitted with a stirbar and septa, then flushed with nitrogen. Tetrahydrofuran (50 mL) was added and the mixture cooled to -78 . A solution of n-butyllithium in hexane (32.3 mL, 80.7 mmol, 2.5 M solution) was added, and the resulting solution was stirred at -78 for 30 minutes. Next, iodomethane (13.0 g, 91.8 mmol) was added and the mixture stirred at -78 for 10 minutes. The reaction solution was quenched with saturated aqueous ammonia hydrochloride solution. The resulting mixture was extracted with EtOAc (3 x 30 mL) and the combined organic layers were washed with brine (50 mL) , dried (MgSO4) and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by chromatography on SiO2(0to 50EtOAc/petroleum ether) to afford 3-methylindolin-2-one. MS (EI) calc?d for C9H10NO [M+H]+, 148 found, 148.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 59-48-3, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ACHAB, Abdelghani Abe; CHRISTOPHER, Matthew P.; FRADERA LLINAS, Francesc Xavier; KATZ, Jason D.; METHOT, Joey L.; ZHOU, Hua; XU, Shimin; FU, Jianmin; FU, Ning; LI, Yabin; WANG, Xichao; (228 pag.)WO2017/166104; (2017); A1;,
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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. 611-09-6, name is 5-Nitroindoline-2,3-dione, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H4N2O4

General procedure: A mixture of isatins or acenaphthoquinone (1 mmol), activated methylene reagents (1 mmol), 1,3-dicarbonyl compounds (1 mmol) and SBA-15-DABCO (0.085 g, 7 mol%) in water was stirred at 25 or 50 C. Upon compilation, monitored by TLC (n-hexane / ethyl acetate 2 / 1), the reaction mixture was allowed to cool to room temperature. The precipitate was filtered and dissolved in acetone. The catalyst was separated by filtration of this solution. The solution was concentrated under vaccum to afford the product, which was purified by recrystallization in the ethanol.

The synthetic route of 611-09-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Baharfar, Robabeh; Azimi, Razieh; Synthetic Communications; vol. 44; 1; (2014); p. 89 – 100;,
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Reference of 1127-59-9, 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. 1127-59-9, name is 7-Methylindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a solution of isatin 1 (1 mmol) in THF (2 mL) was added La(OTf)3 (5 mol percent). The mixture was cooled to -78 °C and stirred at this temperature for 15 min. Then the solution of 2-(trimethylsilyloxy)furan 2 (1.5 mmol) in THF (1 mL) was added dropwise. The mixture was stirred at -78 °C for 2 h. Later the mixture was brought to 20 °C and stirred for additional 0.5-1.5 h (Table 1). The reaction was monitored by TLC. After the completion of the reaction it was diluted with tetrahydrofuran (2.0 mL) and quenched with 10percent aqueous HCl (1.0 mL). The mixture was stirred for 0.25 h at room temperature, neutralized by the addition of a saturated aqueous NaHCO3 solution, and extracted with ethyl acetate (3.x.5 mL). The combined organic layer washed with brine solution, dried over Na2SO4, and concentrated under reduced pressure (rotary evaporator). The crude products were purified by silica gel column chromatography (ethyl acetate/hexanes). The inseparable diastereomers threo/erythro ratio of the product was determined by 1H NMR analysis of the crude reaction mixture.

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

Reference:
Article; Meshram, Harshadas Mitaram; Ramesh, Palakuri; Reddy, Bandi Chennakesava; Sridhar, Balasubramanian; Yadav, Jhillu Singh; Tetrahedron; vol. 67; 17; (2011); p. 3150 – 3155;,
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Synthetic Route of 603-62-3, 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. 603-62-3, name is 3-Nitrophthalimide, This compound has unique chemical properties. The synthetic route is as follows.

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 chemical industry reduces the impact on the environment during synthesis 3-Nitrophthalimide. I believe this compound will play a more active role in future production and life.

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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