Tag: M.W=200-300

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. 20780-72-7, name is 4-Bromoisatin, This compound has unique chemical properties. The synthetic route is as follows., name: 4-Bromoisatin

Into a 250-mL round-bottom flask, was placed 4-bromo-2,3-dihydro-1H-indole-2,3- dione (2.25 g, 9.95 mmol, 1.00 equiv), N,N-dimethylformamide (50 mL), sodium hydride (480 mg, 12.00 mmol, 2.00 equiv), and iodomethane (1.7 g, 11.98 mmol, 1.20 equiv). The resulting solution was stirred for 1 h at room temperature in a water/ice bath. The resulting solution was diluted with 800 mL of EA then washed with 4×50 mL of brine. The organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 2 g (84percent) of 4-bromo-1-methyl-2,3-dihydro-1H-indole-2,3-dione as a red solid

According to the analysis of related databases, 20780-72-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LYCERA CORPORATION; AICHER, Thomas, Daniel; PADILLA, Fernando; TOOGOOD, Peter, L.; CHEN, Shoujun; (331 pag.)WO2016/138335; (2016); A1;,
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Adding a certain compound to certain chemical reactions, such as: 20780-72-7, name is 4-Bromoisatin, 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 20780-72-7, Quality Control of 4-Bromoisatin

General procedure: To a solution of isatin 1 (1 mmol) in toluene (5 mL) was added the solution of trialkyl/aryl Al 2 (2 mmol, 2 M in toluene) dropwise at RT. Then the mixture was heated at 70 °C and stirred for additional 3?3.5 h (see Table 2). The reaction was monitored by TLC. After completion of the reaction, toluene was evaporated and extracted with ethyl acetate (3 × 5 mL). The combined organic layer was washed with brine solution, dried over anhydrous Na2SO4, and concentrated under reduced pressure (rotary evaporator). The crude products were purified by silica gel column chromatography using ethyl acetate/hexanes (4:1?1:1). All compounds were characterized by (MP, NMR, Mass, and IR) spectral data.18

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromoisatin, and friends who are interested can also refer to it.

Reference:
Article; Kumar, G. Santosh; Ramesh, Palakuri; Kumar, A. Sanjeeva; Swetha; Meshram; Tetrahedron Letters; vol. 54; 37; (2013); p. 5048 – 5051;,
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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. 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, A new synthetic method of this compound is introduced below., Formula: C9H4F3NO3

General procedure: To the reaction mixture containing isatin (0.5mmol) in water (2mL), indole (0.5mmol), diethanolamine (20mol %) was slowly added at room temperature. After thecompletion of reaction as monitored by TLC, the reaction mixture was washed with brine solution and then extracted with ethyl acetate. The organic layer was dried over anhydrous Na2SO4 and the product was purified by flash chromatography on the silica gel column using a gradient of petroleum ether/ethyl acetate, as eluent to afford pure products 1-41.

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; Sai Prathima, Parvathaneni; Rajesh, Pamanji; Venkateswara Rao, Janapala; Sai Kailash, Uppalapati; Sridhar, Balasubramanian; Mohan Rao, Mandapati; European Journal of Medicinal Chemistry; vol. 84; (2014); p. 155 – 159;,
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Synthetic Route of 1035235-27-8, A common heterocyclic compound, 1035235-27-8, name is tert-Butyl 4-bromoisoindoline-2-carboxylate, molecular formula is C13H16BrNO2, 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.

Step a. To a stirred solution of tert-butyl 4-bromoisoindoline-2-carboxylate (Intermediate 1, 0.35 g, 1.185 mmol) in 1,4-dioxane: water (4: 1; 20 ml) was added Cs2C03 (0.77 g, 2.371 mmol) at rt under nitrogen. The reaction was purged with nitrogen for 15 min. Pd(PPh3)4 (0.14 g, 0.118 mmol) was added to the reaction mixture and purged with nitrogen for 10 min. 3- (Methoxycarbonyl)phenylboronic acid (CAS Number 99769-19-4; available from Combi Blocks) (0.26 g, 1.422 mmol) was added to the reaction mixture. The reaction mixture was heated at 80C for 24 h. The resulting reaction mixture was cooled to rt, poured into water (20 ml) and extracted with EtOAc (3 x 50). The combined organic phase was washed with brine (80 ml). The organic phase was separated, dried over Na2S04, filtered and concentrated under reduced pressure. The resulting crude material was purified by flash chromatography (5% EtOAc in hexane) yielding tert-butyl 4-(3- (methoxycarbonyl)phenyl)isoindoline-2-carboxylate (0.33 g, 0.932 mmol). LCMS: Method A, 2.782 min, MS: ES+ 298.4 (M-56); 1H NMR (400 MHz, CDC13) delta ppm 8.04 – 8.11 (m, 2 H), 7.62 (d, J=7.2 Hz, 1H), 7.49 – 7.58 (m, 2 H), 7.40 (t, J=7.2 Hz, 1H), 7.31 – 7.33 (m, 1H), 4.69 – 4.79 (m, 4 H), 3.95 (s, 3 H), 1.53 (s, 9 H).

The synthetic route of 1035235-27-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MISSION THERAPEUTICS LIMITED; GIBSON, Karl Richard; JONES, Alison; KEMP, Mark Ian; MADIN, Andrew; STOCKLEY, Martin Lee; WHITLOCK, Gavin Alistair; WOODROW, Michael D; (241 pag.)WO2017/158388; (2017); A1;,
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Application of 169037-23-4, 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. 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

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.

The synthetic route of 5-(Trifluoromethoxy)indoline-2,3-dione has been constantly updated, and we look forward to future research findings.

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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Related Products of 15362-40-0, A common heterocyclic compound, 15362-40-0, name is 1-(2,6-Dichlorophenyl)-2-indolinone, molecular formula is C14H9Cl2NO, 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 4Step a) of preparation of Potassium diclofenacIn a four-necked glass flask the following ingredients were charged:1 -(2,6-dichlorophenyl)-2-indolinone g 100 (moles: 0.359) – Water cc 435- Sodium hydrosulfite g 4- Potassium hydroxide 90 % g 33.6 (moles: 0.539)The mixture was refluxed for 8h 30 min, then cooled to 35 – 37 C. The precipitate was filtered on buchner funnel, then washed with a 1 % NaCI solution in water (cc 70) preheated to 35 C. Wet 180,2 grams of potassium diclofenac were obtained corresponding to dry 1 12,1 grams (Theor. g 120.17).

The synthetic route of 15362-40-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; COSMA S.P.A.; IBSA INSTITUT BIOCHIMIQUE S.A.; AVOGADRI, Alvaro; LUSSANA, Massimiliano; PIZZATTI, Enrica; BARETTI, Sergio; WO2010/69397; (2010); A1;,
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Application of 201940-08-1, 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. 201940-08-1, name is tert-Butyl 5-bromoisoindoline-2-carboxylate belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Synthesis of AM374-A. To a degassed mixture of tert-butyl 5-bromoisoindoline-2- carboxylate (1 g, 3.35 mmol), 1-methylpiperazine (403 mg, 4.03 mmol), Xanthphos (97 mg, 0.17 mmol) and NaOBut (482 mg, 5.03 mmol) in toluene (10 mL) was added Pd2(dba)3 (153 mg, 0.17 mmol) under N2 and the mixture was stirred at 100C overnight. The reaction mixture was concentrated in vacuo. The residue was dissolved in ethyl acetate (50 mL) and washed with brine (30 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography on silica gel (MeOH:CHCl3=99:1~95:5) to give AM374-A (800 mg, 75%) as a white solid

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, tert-Butyl 5-bromoisoindoline-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; RODIN THERAPEUTICS, INC; JEFSON, Martin, R.; LOWE, John, A., III; DEY, Fabian; BERGMANN, Andreas; SCHOOP, Andreas; FULLER, Nathan, Oliver; (165 pag.)WO2017/7756; (2017); A1;,
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Electric Literature of 5394-18-3, 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. 5394-18-3 name is 2-(4-Bromobutyl)isoindoline-1,3-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.

A^-(4-Bromobutyl)phthalimide 7 (9.70 g, 34.40 mmol) was added to a suspension ofpotassium carbonate (8.20 g, 59.30 mmol) andpiperazine-1-carboxylic acid tert-butyl ester 8(5.00 g, 26.80 mmol) in acetone (125 mL). The mixture was heated at reflux for 14 hours. After cooling to ambient temperature, the reaction mixture was filtered and the filtrate concentrated to a waxy yellow solid. Purification by column chromatography (silica gel, gradient of 70:30 to 0:100 hexanes/ethyl acetate, v/v) gave compound 9 (8.69 g, 84 %) as a yellow solid: *H NMR (300 MHz, CDC13) 8 1.45 (s, 9H), 1.46-1.59 (m, 2H), 1.63-1.76 (m, 2H), 2.32-2.40 (m, 6H), 3.38-3.44 (m, 4H), 3.71 (t, J = 6.9 Hz, 2H), 7.71-7.73 (m, 2H), 7.82-7.84 (m, 2H); ESI MS m/z 388 [C21H29N3O4 + H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(4-Bromobutyl)isoindoline-1,3-dione, and friends who are interested can also refer to it.

Reference:
Patent; JOHNSON, Michael, R.; WO2006/23617; (2006); A2;,
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Adding a certain compound to certain chemical reactions, such as: 959235-95-1, name is 6-(Trifluoromethoxy)indoline, 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 959235-95-1, Quality Control of 6-(Trifluoromethoxy)indoline

Under N2 flow at 5C, propylphosphonic anhydride (2.56 ml_, 4.26 mmol) was added dropwise to a mixture of 6-(thfluoromethoxy)indoline [CAS 953906-76-8] (577 mg, 2.84 mmol), 2-(4-chlorophenyl)-2-((3-(2-hydroxyethoxy)-5-methoxy- phenyl)amino)acetic acid 3f (1 .3 g, 3.70 mmol) and diisopropylethylamine (1 .03 ml_, 6.25 mmol) in 2-Me-THF (30 ml_). The mixture was stirred at room temperature for 4 h. Water was added and the mixture was extracted with EtOAc. The organic layer was washed with a 10% solution of K2CO3 in water and then with water, dried over MgSO4, filtered, and the solvent was evaporated under reduced pressure. Purification was carried out by flash chromatography on silica gel, (15-40 muiotatauiota, 40 g, Ch C /MeOH 99/1 ). The pure fractions were combined and evaporated to dryness, to give 2-(4-chlorophenyl)-2-((3-(2-hydroxyethoxy)-5- methoxyphenyl)amino)-1 -(6-(trifluoromethoxy)indolin-1 -yl)ethanone (Compound 3, 800 mg) as a racemic mixture. This fraction was combined with another batch (total amount: 1 .4 g) and crystallized from diisopropyl ether to give 1 .03 g of Compound 3. The enantiomers were separated via Preparative Chiral SFC (Stationary phase: Chiralpak IA 5 muetaeta 250 x 20 mm, Mobile phase: 55% CO2, 45% EtOH (+ 0.3% iPrNh )). The first eluted enantiomer was further purified via reverse phase chromatography (stationary phase: X-bridge-C-18 10 m 30 x 150 mm, mobile phase: 0.2% NH4HCO3/CH3CN gradient 60/40 to 0/100) to give Enantiomer 3A (312 mg). The second eluted Enantiomer 3B (436 mg) was not further purified.

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, 6-(Trifluoromethoxy)indoline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JANSSEN PHARMACEUTICALS, INC.; KATHOLIEKE UNIVERSITEIT LEUVEN; BARDIOT, Dorothee Alice Marie-Eve; BONFANTI, Jean-Francois; KESTELEYN, Bart Rudolf Romanie; MARCHAND, Arnaud Didier M; RABOISSON, Pierre Jean-Marie Bernard; (76 pag.)WO2017/167953; (2017); A1;,
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Adding a certain compound to certain chemical reactions, such as: 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, 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 2058-72-2, category: indolines-derivatives

General procedure: A mixture of corresponding compound 1(0.5 mmol), isatin 3 (0.5 mmol), and sarcosine (0.5 mmol) in acetonitrile (40 mL) (for 1a-c) or in amixture of acetonitrile (30 mL) and chloroform (10 ml) (for 1d-f) was refluxed with stirring for 36 or 72 h for starting compounds 1a-c and 1d-f, respectively. Then the reaction mixture was cooled to room temperature, the precipitate of compounds 4a-e,j,o was filtered off and washed with acetonitrile and water. The reaction mixture of compounds 4f-i,k-n,p-t was concentrated on a rotary evaporator to half of an original volume. After cooling, the precipitate was filtered off and washed with water. Recrystallization from acetonitrile or methanol (4n) gave dispirocompounds 4a-t.

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; Izmest’ev, Alexei N.; Gazieva, Galina A.; Sigay, Natalya V.; Serkov, Sergei A.; Karnoukhova, Valentina A.; Kachala, Vadim V.; Shashkov, Alexander S.; Zanin, Igor E.; Kravchenko, Angelina N.; Makhova, Nina N.; Beilstein Journal of Organic Chemistry; vol. 12; (2016); p. 2240 – 2249;,
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