Category: indolines-derivatives

Reference 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.

General procedure: Compounds 8 and 10 were prepared from azo coupling of aryldiazonium salts 3a,b with5-methoxyindolin-2-one 2, previously described [24]. Aryldiazonium salts were prepared startingto corresponding amines (21.5 mmol) in HCl 6N (11 mL) with water solution (7.5 mL) of sodiumnitrite (23 mmol). This solution was added to solution of indol-2-one (21.5 mmol) and sodium acetate(43 mmol) in methanol (59 mL) at 0 C. The resulting precipitate was filtered and purified.

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:
Article; Purgatorio, Rosa; De Candia, Modesto; De Palma, Annalisa; De Santis, Francesco; Pisani, Leonardo; Campagna, Francesco; Cellamare, Saverio; Altomare, Cosimo Damiano; Catto, Marco; Molecules; vol. 23; 7; (2018);,
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Application of 954-81-4, 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 954-81-4 as follows.

8.7ml (6 · 5 X 102 moles) 1,5-dibromopentane with6 g (3. 2 X 10 2 moles) Phthalimide potassium salt dissolved in 100ml of N, N- dimethylformamide andunder room temperatureit was stirred for 15hours.The solvent was distilled off under reduced pressure, The residue usingn-hexane: ethyl acetate with a volumeratio of 10: 1 eluent to carry out column chromatography, gradually increasingthe polarity to hexane: ethyl acetate with a volume ratio of 5: 1 to give a product of 6.9g(2.3X102 mol) a bromogroup substituted by Phthalimide. The product with 5. 9g (4. 7X 102 mol) of sodium sulfite, 140ml water and 85ml95% ethanol mixed reactionwas heated to 95 C for18h, the remainingsolvent was drained, and the resulting residue was mixed with 73ml ofconcentrated hydrochloric acidthen was heated to 110 C thefor 18H, it was drained, with water – 95% ethanol on the residue to carry out recrystallization to give 5-amino-1-pentylSulfonic acid 2. 7g (total yield 50%).

According to the analysis of related databases, 954-81-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Institute of Chemistry Chinese Academy of Sciences; zhao, jingquan; DENG, HONG; XEI, JIE; (16 pag.)CN101948412; (2016); B;,
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Adding a certain compound to certain chemical reactions, such as: 222036-66-0, name is 5-Aminoisoindolin-1-one, belongs to indolines-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 222036-66-0, category: indolines-derivatives

p-TSA monohydrate (23.12 mg, 0.122 mmol) was added to a stirred solution of 1-(4-((2-chloropyrimidin-4-yl)oxy)naphthalen-1 -yl)-3-(1 -(p-tolyl)-3-(tri methylsi lyl)-1 H-pyrazol-5-yl)urea (see Example 6(i) above; 33 mg, 0.061 mmcl) and 5-aminoisoindolin-1-one (18.01 mg, 0.122 mmol) in THFDMF (1 mL, 1:1). The resulting mixture was heated at 60 °C overnight. The reaction was cooled to rt then diluted with EtOAc (15 mL). The suspension was filtered, the product was detected in the filtrate which was subsequentlyconcentrated in vacuo. The crude product was purified by chromatography on silica gel (12 g column, 0-10percent MeOH in DCM) to afford a white solid. The crude product was purified by preparative HPLC (Waters, Acidic (0.1percent Formic acid), Waters X-Select PrepC18, 5 pm, 19×50 mm column, 35-75percent MeCN in Water) to afford the title compound (7 mg) as a white solid.1H NMR (DMSO-d6) 400 MHz, O: 9.93 (s, 1H), 9.24 (s, 1H), 8.84 (s, 1H), 8.47 (d, 1H),8.22 (s, 1H), 8.11 (d, 1H), 8.00 (d, 1H), 7.82-7.80 (m, 1H), 7.65-7.61 (m, 1H), 7.58-7.54(m, 1H), 7.53-7.36 (m, 6H), 7.34-7.25 (m, 2H), 6.70 (d, 1H), 6.65 (s, 1H), 3.99 (s, 2H),2.41 (s, 3H), 0.27 (s, 9H).LCMS mz 655 (M+H)+ (ES+).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; RESPIVERT LIMITED; TOPIVERT PHARMA LIMITED; FYFE, Matthew, Colin, Thor; MEGHANI, Premji; THOM, Stephen, Malcolm; WO2014/33449; (2014); A1;,
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Synthetic Route of 14192-26-8, These common heterocyclic compound, 14192-26-8, name is Methyl 2-oxoindoline-6-carboxylate, 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.

Room temperature, 2-indolone-6- methyl formate(5-2) (4.0g, 20 . 71mmol) suspended in 12 ml in toluene of, the chloroactic anhydride (5.4g, 30 . 95mmol) into the above-mentioned suspension, heating reflow 3h, cooling to 80 C, 30 min by adding methyl cyclohexane (6 ml), stirring suspension of cooling to room temperature, filtered to obtain crude products, with cold methanol (4 ml) washing, drying the white solid obtained 5.155g (93.5%), i.e. compound 1-cholroacetyl- 2-indolone-6- methyl formate (6-2).

The synthetic route of 14192-26-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sichuan University; Chen, Yuanwei; Xie, Yongmei; Wei, Yuquan; (32 pag.)CN104003925; (2016); B;,
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Reference of 1677-48-1, A common heterocyclic compound, 1677-48-1, name is 5,6-Dichloroindoline-2,3-dione, molecular formula is C8H3Cl2NO2, 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.

7.5 g of 1-bromo-2-methoxybenzene are added dropwise to a suspension of 1.1 g of magnesium in 20 ml of ether containing a few crystals of iodine, the reflux being maintained once it has started. At the end of the addition, the mixture is heated at reflux for 2 hours. A suspension of 4.3 g of 5,6-dichloro-1H-indole-2,3-dione in 20 ml of THF is then added and the resulting mixture is refluxed for 30 minutes. After cooling to RT, the reaction mixture is poured into a water/ice/concentrated HCl mixture and extracted with EtOAc, the organic phase is dried over Na2SO4 and the solvent is evaporated off under vacuum. The residue is triturated in hot iso ether and the precipitate formed is filtered off by suction and washed with ether. 5.2 g of the expected product are obtained, m.p.=245-246 C.

The synthetic route of 1677-48-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Di Malta, Alain; Garcia, Georges; Roux, Richard; Schoentjes, Bruno; Serradeil-Le Gal, Claudine; Tonnerre, Bernard; Wagnon, Jean; US2004/180878; (2004); 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. 181140-34-1, name is (R)-(-)-N-(2,3-Epoxypropyl)phthalimide, A new synthetic method of this compound is introduced below., COA of Formula: C11H9NO3

General procedure: Suspension of starting compound (2a-e) and (S)-N-(2,3-epoxypropyl)phthalimide or (R)-N-(2,3-epoxypropyl)phthalimide (1 eq.) in absolute ethanol (0.2 M) was refluxed for 15 h. The crude product precipitated from clear solution at 0 C. Compounds 3a-f were purified either by flash column chromatography using EtOAc/hexane as eluant or by recrystallization from absolute ethanol.

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; Trstenjak, Uro?; Ila?, Janez; Kikelj, Danijel; European Journal of Medicinal Chemistry; vol. 64; (2013); p. 302 – 313;,
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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. 39603-24-2, name is 5,7-Dimethylindoline-2,3-dione, A new synthetic method of this compound is introduced below., Recommanded Product: 39603-24-2

General procedure: An equimolar mixture of dipolarophile 1/7 (1 mmol), isatin 2a-e/acenaphthenequinone 11 (1 mmol) and sarcosine 3/1,3-thiazolane-4-carboxylic acid 5 (1 mmol) in 2,2,2-trifluoroethanol (10 ml) was refluxed forthe appropriate time (30-40 min). After completion of the reaction asindicated by (TLC), the solid precipitates were filtered and washed withethanol to furnish pure corresponding dispiropyrrolidine/thiapyrrolizidinederivatives. Synthesized compounds were well characterized by 1H NMR, 13CNMR, Mass and single crystal X-ray analysis of representative compounds.

The synthetic route of 39603-24-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Dandia, Anshu; Singh, Ruby; Khan, Shahnawaz; Kumari, Sukhbeer; Soni, Pragya; Tetrahedron Letters; vol. 56; 30; (2015); p. 4438 – 4444;,
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Reference of 169037-23-4, 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 169037-23-4 as follows.

General procedure: A mixture of indoline-2,3-dione 1 (1mmol), l-tryptophan (2a) or l-histidine 2b (1mmol) and (E)-(2-nitrovinyl)benzene 3 (1.1mmol) was heated while stirred in [bmim]Br as the reaction medium (3mL) for 1hat 100C. After completion of the reaction (TLC), EtOAc (5mL) was added and the reaction mixture was stirred for 10min. This treatment was repeated and the combined ethyl acetate layers were removed in vacuo. The crude product was purified by recrystallization of the residue from EtOH (compounds 4) or by column chromatography (compounds 5). After extraction of the product, the ionic liquid was dried under vacuum at 80C for 2h to eliminate any water and could be reused for subsequent runs of the reaction.

According to the analysis of related databases, 169037-23-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Arumugam, Natarajan; Almansour, Abdulrahman I.; Kumar, Raju Suresh; Periasamy, Vaiyapuri Subbarayan; Athinarayanan, Jegan; Alshatwi, Ali A.; Govindasami, Periyasami; Altaf, Mohammad; Menendez, J. Carlos; Tetrahedron; vol. 74; 38; (2018); p. 5358 – 5366;,
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Reference of 5332-26-3,Some common heterocyclic compound, 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, molecular formula is C9H6BrNO2, 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: Appropriate bromide (1.5 mmol) was dissolved in 15 mL of DMF (dried) and sodium azide (1.6 mmol, 104 mg) was added. The mixture was stirred vigorously at room temperature. After 12 h the reaction was quenched by adding 15 mL of distilled water (slightly exothermic reaction). The cooled reaction mixture (room temperature) was extracted twice with 30 mL of diethyl ether and washed with water (once with 20 mL). The separated organic layer was dried over anhydrous sodium sulphate and evaporated to dryness. The product obtained as white solid was washed with 30mL of distilled water.

The synthetic route of 5332-26-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Pyta, Krystian; Klich, Katarzyna; Domagalska, Joanna; Przybylski, Piotr; European Journal of Medicinal Chemistry; vol. 84; (2014); p. 651 – 676;,
Indoline – Wikipedia,
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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. 50727-04-3, name is 5-Methoxyisoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Computed Properties of C9H7NO3

EXAMPLE 4 4-(1,3-Dioxo-5-methoxy-1,3-dihydroisoindol-2-yl)-2-{1-[2-(4-methoxy-phenyl)-1-(methylcarbamoyl)ethylcarbamoyl]cyclohexylmethyl}butyric acid 4-(1,3-Dioxo-5-methoxy-1,3-dihydroisoindol-2-yl)-2-{1-[2-(4-methoxy-phenyl)-1-(methylcarbamoyl)ethylcarbamoyl]cyclohexylmethyl}butyric acid (mixture of diastereomers) starting with the reaction of 4-hydroxy-2-{1-[2-(4-methoxyphenyl)-1-(methylcarbamoyl)ethylcarbamoyl]cyclohexylmethyl}butyric acid tert-butyl ester with 1,3-dioxo-5-methoxy-1,3dihydroisoindole.

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; Pfizer Inc.; US5854275; (1998); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem