Month: July 2021

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. 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 5-Bromo-1-methylindoline-2,3-dione

In a 50 mL reaction flask,Triethylamine (40 mg, 0.4 mmol)Was added to a solution of 1-methyl-5-bromoisatin (240 mg, 1.0 mmol)1-cyanoacetylguardane azulene (344 mg, 1.3 mmol)And malononitrile (86 mg, 1.3 mmol)In acetonitrile (30 mL)Heated to reflux for 7 hours (monitored by silica gel chromatography (TLC)). After completion of the reaction,The reaction mixture was concentrated under reduced pressure and recrystallized from acetic acid to give a blue solid in 80% yield.

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 2058-72-2.

Reference:
Patent; Bohai University; Wang Daolin; Zhang Weinan; Xing Jinjuan; (14 pag.)CN106220641; (2016); A;,
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Related Products of 20870-79-5, 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 20870-79-5 as follows.

5-Amino-2-oxindole 5-Nitro-2-oxindole (6.3 g) was hydrogenated in methanol over 10% palladium on carbon to give 3.0 g (60% yield) of the title compound as a white solid.

According to the analysis of related databases, 20870-79-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sugen, Inc.; US6486185; (2002); B1;; ; Patent; Sugen, Inc.; US6114371; (2000); A;,
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Related Products of 71294-03-6, These common heterocyclic compound, 71294-03-6, name is 7-Fluoroindolin-2-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.

Example 53Preparation of 5-f(2-(riS.2SV2-ri-(5-chloropyrimidin-2-vnpiperidin-4- yllcYclopropyUethy?aminol-T-fluoro- 1 ,3-dihvdro-2H-indol-2-oneStep 1: 7-fluoro-5-tauiitro-L3-dihvdro-2H-indol-2-one7-fluoro-1,3-dihydro-2H-indol-2-one (8.Og, 52.9 mmol) was slurried in H2SO4 (cone, 86 ml) and the mixture cooled to -45 C. A solution of fuming nitric acid (>90%, 3.34 g, 52.9 mmol) in H2SO4 (20 ml) was added drop wise, while maintaining the temperature at -45 C throughout the addition. The mixture was allowed to slowly warm to RT and stirred overnight. The mixture was poured into stirred ice-cold water (1500 ml). A white precipitate resulted, and the slurry was aged at 0 C for 1 hour. The solid was collected by filtration, triturated with cold water (2x), and dissolved into EtOAc (1 L). TWs solution was washed with basic brine (containing sodium bicarbonate), dried over Na2SO4, filtered, and the volatiles removed in vacuum to give the titled compound.

The synthetic route of 71294-03-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WOOD, Harold, B.; ADAMS, Alan, D.; SZEWCZYK, Jason, W.; ZHANG, Yong; YANG, Meng; WO2011/19538; (2011); A1;,
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Application of 104618-32-8, 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. 104618-32-8, name is 2-(4-Oxocyclohexyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 4 3-Amino-6-bromo-1,2,3,4-tetrahydrocarbazole hydrochloride Reaction of 4-bromophenylhydrazine hydrochloride (4.0 g, 18.1 mmol) with 4-phthalimido-cyclohexanone (4.39 g, 18.1 mmol) in refluxing n-butanol for 20 min, followed by cooling, filtration, and evaporation of the filtrate to dryness yielded 3-phthalimido-6-bromo-1,2,3,4-tetrahydrocarbazole as an orange solid (7.45 g).

The synthetic route of 2-(4-Oxocyclohexyl)isoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SmithKline Beecham P.L.C.; US5464864; (1995); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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 17630-75-0 as follows. Quality Control of 5-Chloro-2-oxindole

A mixture of 5-chlorooxindole (6.98 g, 41.6 mmol), 3,5-dimethyl-1H-pyrrole-2-carboxaldehyde (5.12 g, 41.6 mmol) and piperidine (410 muL, 4.16 mmol) in 200 mL of EtOH was heated at reflux for 8 h. The reaction mixture was cooled to room temperature and filtered to give the title compound (4.50 g, 40%) as a red/orange solid.

According to the analysis of related databases, 17630-75-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Allergan, Inc.; US2004/102509; (2004); A1;,
Indoline – Wikipedia,
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These common heterocyclic compound, 7699-18-5, name is 5-Methoxyindolin-2-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. name: 5-Methoxyindolin-2-one

General procedure: To a solution of 4-(4-(hydrazinecarbonyl)-5-phenyl-1H-pyrazol-1-yl)benzenesulfonamide (10) (10 mmol, 0.36 g) in 20 mL ethanol, 10 mmol of 5-(un)substituted isatin or N-benzyl isatin was added followed by catalytic amount of acetic acid (0.5 mL). The reaction mixture was refluxed for 1 h. The formed precipitate, in case of 11a-e, was filtered, washed with hot ethanol and recrystallizedf rom DMF/ EtOH to give the targeted compounds 11a-e. Concerning compound 11f, the precipitate formed after cooling was filtered and recrystallized from DMF/ EtOH. 4.1.5.4 4-(4-(2-(5-Methoxy-2-oxoindolin-3-ylidene)hydrazine-1-carbonyl)-5-phenyl-1H-pyrazol-1-yl)benzenesulfonamide (11d) Orange powder, 81% yield; mp > 300 C. IR (KBr) numax/cm-13414-3190 (NH2, NH), 1722-1690 (C=O), 1512 (C=N), 1322, 1156 (SO2). 1H NMR (DMSO-d6, 300 MHz) delta 3.77 (s, 3H, OCH3), 6.81 (dd, 1H, J = 11.4, 8.6 Hz, H-7 of isatin), 6.91-7.08 (m, 1H, Ar-H), 7.30-7.43 (m, 6H, Ar-H), 7.45 (s, 2H, SO2NH2, D2O exchangeable), 7.80 (d, 2H, J = 8.7 Hz, Ar-H), 8.34, 8.49 (2s, 1H, H-3 of pyrazole), 10.55, 11.02 (2s, 1H, NH isatin, D2O exchangeable), 11.31, 13.12 (2s, 1H, NH hydrazone, D2O exchangeable). 13C NMR (DMSO-d6, 75 MHz) delta 55.58, 105.73, 110.91, 111.91, 112.39, 115.65, 118.23, 120.46, 125.74, 126.50, 128.29, 129.23, 130.23, 135.90, 137.35, 141.14, 142.19, 143.31, 154.45, 155.32, 162.60, 164.74. MS m/z [%] 516 [M+, 7.62], 326 [100]. Anal. Calcd for C25H20N6O5S (516.53): C, 58.13; H, 3.90; N, 16.27; S, 6.21. Found: C, 58.30; H, 3.96; N, 16.38; S, 6.32.

The synthetic route of 5-Methoxyindolin-2-one has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ibrahim, Hany S.; Abou-Seri, Sahar M.; Tanc, Muhammet; Elaasser, Mahmoud M.; Abdel-Aziz, Hatem A.; Supuran, Claudiu T.; European Journal of Medicinal Chemistry; vol. 103; (2015); p. 583 – 593;,
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Related Products of 20780-77-2, 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. 20780-77-2 name is 6-Iodoindoline-2,3-dione, 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.

Method IAccording to this method Examples 1-14 and 22-24 were prepared. The indirubin derivatives are prepared according to Russel G. A., Kaupp G. (1969), J. Am. Chem. Soc., 91, pages 3851-3859. ; Example 1 6-iodo-indirubinYield: 68%, fine deep-purple powderCHN-analysis: C16H9IN2O2 (MW: 388.16 g/mol) calc.: 49.5%; C, 2.3%; H, 7.2%; N. found: 49.3%; C, 2.1%; H, 7.1%; N.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Iodoindoline-2,3-dione, and friends who are interested can also refer to it.

Reference:
Patent; Faustus Forschungs Cie. Translational Cancer Research GmbH; US6987092; (2006); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 356068-93-4, name is (Z)-5-((5-Fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. category: indolines-derivatives

To a stirred solution of compound 109 (0.5 g, 1.67 mmol) in DMF( 40 mL) at O0C was added etaOBt (0.34 g, 2.5 mmol), triethylamine (0.94 mL, 6.68 mmol), ECDI etaC1 (0.48 g, 2.5 mmol) and compound 303 (0.44 g, 2.0 mmol) successively. The mixture was stirred overnight at room temperature, evaporated, diluted with water (50 mL), brine (50 mL) and saturated aqueous sodium bicarbonate(50 mL). The peta of solution was adjusted to 11-12 with 1OM NaOH. The mixture was filtered, washed with water, dried to obtain desired product 304 as a yellow solid (630 mg, 75%). LCMS: 504 [M+l]+, 1H NMR (DMSO-J6): delta 2.39 (s, 3H), 2.41 (s, 3H), 3.59 (m, 2H), 3.69 (s, 3H), 4.15 (t, J= 4.5 Hz, 2H), 6.45 (d, IH), 6.94 (m, 4H), 7.65 (m, 6H), 10.87 (s, IH), 13.66 (s, IH).

The synthetic route of 356068-93-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CURIS, INC.; WO2008/33747; (2008); A2;,
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Synthetic Route of 423116-18-1, 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. 423116-18-1, name is 2-(4-Oxocyclohexylmethyl)isoindole-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

3-tert-Butyl-11-phthalimidomethyl-7,14,15-trioxadispiro[5.1.5.2]pentadecane (OZ384). A solution of O-methyl 4-tert-butylcyclohexanone oxime (2.74 g, 15 mmol) and 4-phthalimidomethylcyclohexanone (2.57 g, 10 mmol) in cyclohexane (100 ml) and CH2Cl2 (100 ml) was treated with ozone according to the general procedure. The reaction mixture was concentrated, triturated with ethanol (50 ml), and filtered. The cake was purified by flash chromatography (silica gel, 10% EtOAc in hexanes) to afford trioxolane OZ384 (0.41 g, 10%) as a colorless solid. mp 175 C. dec; 1H NMR (500 MHz, CDCl3) delta0.86 (s, 9H), 0.94-1.05 (m, 1H), 1.21-1.42 (m, 4H), 1.47-2.02 (m, 13H), 3.56 (d, J=7.3 Hz, 2H), 7.70-7.74 (m, 2H), 7.81-7.87 (m, 2H); 13C NMR (125.7 MHz, CDCl3) delta24.50, 27.66, 27.81, 32.29, 33.43, 34.54, 35.59, 43.10, 47.23, 108.74, 108.89, 123.24, 132.00, 133.92, 168.53. Anal. Calcd for C25H33NO5: C, 70.23; H, 7.78; N, 3.28. Found: C, 70.46; H, 7.90; N, 3.43.

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, 2-(4-Oxocyclohexylmethyl)isoindole-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MEDICINES FOR MALARIA VENTURE MMV; US2005/256185; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 675109-26-9, name is 6-Bromoisoindolin-1-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. name: 6-Bromoisoindolin-1-one

6-(4-Hydroxy-but-1-ynyl)-2,3-dihydro-isoindolin-1-oneTo a mixture of 6-Bromo-2, 3-dihydro-isoindolin-1-one (3Og, 0.14mole), bis (triphenylphosphine) palladium dichloride (5 g, 0.007 mole), CuI (2.6 g, 0.01 mole), dry Et3N (700 mL) in dry DMF (700 mL) was added 3-butyn-1-ol (21.3 mL, 0.28 mole) slowly drop- wise. The reaction mixture was bubbled with argon for 20 min and heated at 100 C for 24 h. The solvent was evaporated and the crude residue was washed with DCM (100 mL), filtered and dried to 6-(4-Hydroxy-but-1-ynyl)-2,3-dihydro-isoindolin-1-one as a pale grey solid (24 g, 85%). 1H-NMR (DMSO-d6, 300 MHz): delta 8.6 (1H1 s), 7.5-7.6 (2H, d), 7.5 (1H,s), 4.9 (1H, t), 4.3 (2H1 s), 3.6-3.7 (2H, t), 2.4-2.6 (2H, t); MS: M+1: 202 (201)

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

Reference:
Patent; PFIZER PRODUCTS INC.; WO2008/20306; (2008); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem