Author: Jessica.F

Reference of 21544-81-0, 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. 21544-81-0, name is 4,6-Dimethoxyindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

3,5-dimethoxy aniline (199g, 1.30mol) in diethyl ether (5.0 L) was added inthe flask 5L3 Cooled to 0 C. After 45 minutes the HCl gas (227g)introduced into the solution.at 10C 45 Minutes the mixture was filtered, (4L) and washed withisopropyl acetate, under high vacuum, dried at 45 C Night to give the hydrochloride as a white solid (242.3g, 98%). Under stirring the above hydrochloride (20g, 0The mixture.105mol) and oxalyl chloride (33 mL of) isequipped with a reflux condenser, 3-neck flask was heated 2 Hour (170 C externaltemperature), oxalyl chloride was distilled off from the reactionmixture. The flask was cooled to 0 C, was added methanol (40mL). The reactionmixture was heated at reflux for 45 minutes, filtered while hot, with A Alcohol(80mL) and washed to give a yellow-green solid4,6-dimethoxy isatin (17.2g, 79%). After 2 Hour to isatin (162g,0.78mol) was heated in aqueous NaOH solution(40%, 1.5L) in (externalTemperature 70 C) was slowly added to H 2 O 2(35%, 405mL). H 2 O 2 was added after each batch, the internal temperature of the reaction Degree(initially 64 C) increase (to a maximum temperature of 80 C). Afterthe addition was complete, then at 70 C will blister The reaction mixture wasstirred for an additional 2hours, the mixture was stirred overnight while cooling to roomtemperature. The mixtureIt was heated to 70 C. An additional H 2 O 2 (75mL), at 70 C and themixture was stirred for an additional 2 Hours until the reaction was complete.Cooled to 10 C (bath temperature), a solution of Na 2 S 2 O 3 solution (150mL, saturation). The mixture was washed with HCl (37%, 1.6L) was adjusted to pH8, with acetic acid(glacial acetic acid, 75mL) transfer To pH6, while not allowing thereaction mixture was warmed exceed 40 C. The reaction mixture was filtered,washed with water (4L) and washed to give the desired brownsolid amino acid (83.7g, 55%). The amino acid (82.7g, 0.42mol) (4.2L) was added in dry THF EDCl (89.2g, 0.48mol), HOBT(65g, 0.48mol) and NMM (51.3mL), and the mixturewas stirred at roomtemperature for 3 hours. Adding NH3 Aqueoussolution (83mL, 50%), and the mixture was stirred at room temperature for 16 hours.Was added water (1.25L), the The mixture (2 × 250mL) and extracted with DCM.Then the combined extracts were washed with water (2 × 500mL) washed Fandi.Concentrated, slurried with ethyl ether (550mL), filtered, and dried under highvacuum to afford a brown The solid4,6-dimethoxy-2-amino-benzamide (46.7g, 57%).2-Amino-4,6-dimethoxy – benzamide (1.06g, 5.4mmol), 3,5- dimethyl-4-hydroxy Benzaldehyde (0.810g,5.4mmol), K 2 CO 3 (0.747g, 5.4mmol) and I 2(1.645g, 6.5mmol) DMF (20mL) in mixing, at 80 C and the reaction mixture was heated for 12 hours. It was cooledto Room temperature, poured onto crushed ice. The solid was collected, whichwas purified by column chromatography to give a white solid State of 2- (4-hydroxy-3,5-dimethylphenyl)-5,7-dimethoxy-quinazolin -4 (3H) – one (0.9g, 51%). Selected data:MP291-293 C.

The synthetic route of 4,6-Dimethoxyindoline-2,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RESVERLOGIX CORP; HANSEN, H; (62 pag.)CN103319408; (2016); B;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 675109-26-9, name is 6-Bromoisoindolin-1-one, molecular formula is C8H6BrNO, 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

A mixture of 6-bromoisoindolin-1-one (2.0 g, 9.44 mmol), bis(pinacolato)diboron (2.41 g, 9.7 mmol), KOAc (1.86 g, 18.66 mmol) and Pd(dppf)2C12 (0.39 g, 0.49 mmol) in dioxane (50 mE) was stirred at 1000 C. overnight under a nitrogen atmosphere. The mixture was poured into water and extracted with EtOAc (100 mLx3). The combined organic fractions were washed with brine, dried over sodium sulfate and concentrated under vacuum. The residue was purified by chromatography on silica gel (1/10 to 1/5 EtOAc in pet. ether) to give compound 13A (600 mg, 25% yield) as a white solid. ESI mlz 260.0 [M+1].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 675109-26-9, its application will become more common.

Reference:
Patent; Seal Rock Therapeutics, Inc.; BROWN, Samuel David; US2018/291002; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 2058-72-2, 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 2058-72-2 as follows.

General procedure: The mixture of corresponding 2-amino-4-arylimidazoles 1 (1.0 mmol), isatin 18 (1.0 mmol) andmalononitrile 12 (1.0 mmol) in 2 mL of 2-propanol was refluxed during 50-60 min. After cooling, the solid products 19 were filtered off and crystallized from iPrOH.

According to the analysis of related databases, 2058-72-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Lipson, Victoria V.; Pavlovska, Tetiana L.; Svetlichnaya, Nataliya V.; Poryvai, Anna A.; Gorobets, Nikolay Yu.; Van Der Eycken, Erik V.; Konovalova, Irina S.; Shiskina, Svetlana V.; Borisov, Alexander V.; Musatov, Vladimir I.; Mazepa, Alexander V.; Beilstein Journal of Organic Chemistry; vol. 15; (2019); p. 1032 – 1045;,
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 22190-33-6 as follows. Computed Properties of C8H8BrN

To a solution of 5-bromo-2,3-dihydro-1H-indole (2.11 g, 10.7 mmol) in 40 mL of THF was added Boc2O (2.56 g, 11.7 mmol). The reaction mixture was stirred at room temperature for 18 hours, and then concentrated under reduced pressure. Purification of the residue via flash chromatography (8% EtOAc in hexane) afforded 5-bromo-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester (2.59 g, 95%) as a white solid; MS (M+H)=298.

According to the analysis of related databases, 22190-33-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Carter, David Scott; Schoenfeld, Ryan Craig; Weikert, Robert James; US2008/45543; (2008); 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. 59-48-3, name is Indolin-2-one, A new synthetic method of this compound is introduced below., Formula: C8H7NO

(e) Preparation of 5-Bromo-2-oxindole. 2-Oxindole (1.3 g) in 20 mL of acetonitrile was cooled to -10 C. and 2.0 g of N-bromosuccinimide was slowly added with stirring. The reaction was stirred for 1 hour at -10 C. and 2 hours at 0 C. The precipitate was collected, washed with water and dried to give 1.9 g (90% yield) of the title compound.

The synthetic route of 59-48-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sugen, Inc.; US6147106; (2000); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, belongs to indolines-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Recommanded Product: 5332-26-3

To a solution of diisopropylamine (2.33 g, 23.0 mmol) in THF (35 mL) at -78 C. was added n-butyllithium (21.2 mmol, 13.3 mL of a 1.6 M solution). After stirring for 15 min, the imine (4.0 g, 17.7 mmol) from reaction (31a) in THF (20 mL) was added dropwise. The mixture was allowed to stir for 1 h. N-(Bromomethyl)phthalimide (5.1 g, 21.2 mmol) was dissolved in THF (20 mL) and was added dropwise to the enolate. After stirring for 1 h at -78 C., the reaction was warmed to rt overnight. The reaction was quenched with water (2 mL) and the mixture concentrated under reduced pressure. The remaining residue was treated at 0 C. with 1 M hydrochloric acid/methanol (100 mL) for 20 min followed by warming to rt for an additional 40 min. After removing the methanol in vacuo, the water layer was neutralized with sodium bicarbonate and extracted with ethyl acetate. The organic layer was dried and concentrated to give the desired amine (2.6 g, 57%). MS found: (M+H)+=263.

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

Reference:
Patent; Duan, Jingwu; King, Bryan W.; Decicco, Carl; Maduskuie JR., Thomas P.; Voss, Mathew E.; US2004/72802; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 19727-83-4, 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. 19727-83-4, name is 6-Nitroindoline, This compound has unique chemical properties. The synthetic route is as follows.

6-Aminoindoline. A solution of 6-nitroindoline (1 g, 6.1 mmol) in 50 mL of ethyl acetate was hydrogenated under an atmosphere of hydrogen with Pd-C 10% (100 mg) at rt for 3 h. Filtration over celite afforded 1.0 g (98%) of 6-aminoindoline. Data for 6-aminoindoline: 1 N NMR (400 MHz, CDCl3) 7.40 (d, J=7.4, 1H), 6.05 (d, J=2.0, 1H), 6.03 (d, J=7.5, 1H), 3.67 (bs, 1H), 3.49 (t, J=8.1, 2H), 3.48 (bs, 2H), 2.90 (t, J=8.2, 2H).

The chemical industry reduces the impact on the environment during synthesis 6-Nitroindoline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Ligand Pharmaceuticals Incorporated; US5696133; (1997); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 14192-26-8, 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. 14192-26-8 name is Methyl 2-oxoindoline-6-carboxylate, 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.

Under the room temperature, 19.1g (100mmol) methyl 2-oxindole-6-carboxylate was suspended in 60 ml toluene. Then add 25.6g (150mmol) chloroacetic anhydride. The mixture at 120 C was heated under reflux for 3 hours, then cooled to 80 C, and in 30 min panega 30 ml methyl cyclohexane, and slowly to room temperature; separating the mother liquor, and with the freezing methanol washing the solid, dry, to obtain white crystal 25.36g, the target compound, the yield is 95%.

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

Reference:
Patent; Southeast University; Ji, Min; Chen, Hao; Cai, Jin; Liu, Haidong; Li, Rui; (13 pag.)(2016);,
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. 7699-18-5, name is 5-Methoxyindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C9H9NO2

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%).

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 7699-18-5.

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;,
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. 885272-46-8, name is tert-Butyl 4-bromoindoline-1-carboxylate belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C13H16BrNO2

A mixture of the product of Step 1 (1.5 g, 5.0 mmol), allyltributylstannane (2.48 g, 7.5 mmol) and Pd(PPh3)4 (0.58 g, 0.5 mmol) in toluene (20 mL) was stirred at 100 C overnight under a nitrogen atmosphere. The mixture was loaded directly to a silica gel loading cartridge and purified by silica gel column chromatography with EtOAc in hexanes (0 to 10% gradient) to give the title compound (0.88 g, 68%). 1H NMR (CDC13) delta: 7.76 (br. s, 1H), 7.15 (t, J=7.7 Hz, 1H), 6.80 (d, J=7.6 Hz, 1H), 5.88- 5.98 (m, 1H), 5.01-5.11 (m, 2H), 3.93-4.09 (m, 2H), 3.32 (d, J=6.3 Hz, 2H), 3.04 (t, J=8.7 Hz, 2H), 1.57 (s, 9H).

The synthetic route of 885272-46-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PTC THERAPEUTICS, INC.; WANG, Jiashi; GERASYUTO, Aleksey, Igorevich; ARNOLD, Michael, A.; KARP, Gary, Mitchell; QI, Hongyan; WOLL, Matthew, G.; ZHANG, Nanjing; BRANSTROM, Arthur, A.; NARASIMHAN, Jana; DUMBLE, Melissa, L.; HEDRICK, Jean; WEETALL, Maria, L.; (260 pag.)WO2016/25933; (2016); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem