Month: March 2021

Synthetic Route of 169037-23-4, A common heterocyclic compound, 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, molecular formula is C9H4F3NO3, 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.

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 169037-23-4 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;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 3484-35-3,Some common heterocyclic compound, 3484-35-3, name is 5-Methylindolin-2-one, molecular formula is C9H9NO, 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: To a solution of appropriate oxindole (7a-e, 0.3 mmol) in ethanol (3 mL) was added corresponding aldehydes (11a-e,0.32 mmol) and a catalytic amount of piperidine. The reaction mixture was stirred at reflux for 6-12 h (reaction monitored byTLC). After cooling, the precipitate was filtered, washed with cold ethanol, and dried in air to furnish pure (Z)-3-(3′-methoxy-4′-(2-amino-2-oxoethoxy)-benzylidene)indolin-2-ones title compounds of formula (4a-v) as yellow/brown/orange solids in moderate to excellent yields.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Methylindolin-2-one, its application will become more common.

Reference:
Article; Senwar, Kishna Ram; Reddy, T. Srinivasa; Thummuri, Dinesh; Sharma, Pankaj; Naidu; Srinivasulu, Gannoju; Shankaraiah, Nagula; European Journal of Medicinal Chemistry; vol. 118; (2016); p. 34 – 46;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 20780-72-7, A common heterocyclic compound, 20780-72-7, name is 4-Bromoisatin, molecular formula is C8H4BrNO2, 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.

(3) 10 mL DMF dissolution step (2) The obtained compound 4.4 mmol, 1.8 g of potassium carbonate, 1.1 g of 4-chlorobenzyl bromide, and stirred under argon atmosphere for 2 hours at room temperature; TLC analysis determined that after the reaction was completed, The reaction was quenched by the addition of excess ice water and stirred for 30 minutes; Filter the suspension and dry the filter cake. Obtained as a red solid (Compound 4b 1.34 g, yield 90percent, without further purification);

The synthetic route of 20780-72-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tianjin University of Science and Technology; Diao Aipo; Li Yuyin; Yu Peng; Liu Yang; Li Zhipeng; (15 pag.)CN109574907; (2019); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 446292-08-6, name is (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-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 446292-08-6, Application In Synthesis of (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione

In a four neck round bottom flask, charged methanol (2900 ml), 2-([(5S)-2- Oxo-3-[4-(3-oxo- 4-morpholinyl)phenyl]-l,3-oxazolidin-5-yl}methyl)-lH-isoindole-l,3(2H)-dione (290 g), and 40% aqueous methylamine (265 g) at 25 to 30C. Reaction mass is stirred for 1 h at 25 to 30C and then heated to 60 to 65C, and maintained at same temperature for 4 h. Reaction mixture then cooled to 25 to 30C and added cone, hydrochloric acid (290 ml, pH should be 1 to 2) and stirred for 30 minutes. Obtained solid is filtered off and washed by chilled methanol (290ml). Yield= 92.0%

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, (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; WANBURY LTD.; DR. NITIN SHARADCHANDRA PRADHAN; DR. NILESH SUDHIR PATIL; DR. RAJESH RAMCHANDRA WALAVALKAR; MR. NILESH SUBHAS KULKARNI; MR. SANDIP BABANRAO PAWAR; MR. TARAK SAMBHAJI PAWAR; WO2014/102820; (2014); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 667463-64-1,Some common heterocyclic compound, 667463-64-1, name is 6-Bromo-1-methylindoline-2,3-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.

1-3. I (JS.O g, 63 nunol) and hydrazine hydrate (30 mL, 618 nunol) are heated to 12S C for 72 h.To the cool reaction mixtw-e DCM is added and extracted with water and 1 M HCI. The organiclayer is dried over MgS04 and concentrated. The crystaJlized residue is dissolved in DCM,methanol is added and the DCM is removed in vacuo. The crystallized product is filtered by sunction and washed with cold methanol. Yield 63%, mz 226/228 [M+H]+, rt J.l6 min, LC-MSMethod VOOJ 003.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Bromo-1-methylindoline-2,3-dione, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GRAUERT, Matthias; ANDERSKEWITZ, Ralf; GRUNDL, Marc; OOST, Thorsten; PAUTSCH, Alexander; PETERS, Stefan; WO2014/140081; (2014); A1;,
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. 2058-74-4, name is 1-Methylisatin belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 1-Methylisatin

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 synthetic route of 2058-74-4 has been constantly updated, and we look forward to future research findings.

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;,
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 87-48-9 as follows. Safety of 5-Bromoindoline-2,3-dione

Step 90a: 5-Bromoindolin-2-one (Compound 0601-194)[0597]To a mixture of 5-bromoindole-2,3-dione (2.25 g, 10 mmol), ethyleneglycol (45 mL) and hydrazine hydrate (1.06 g, 21.10 mmol) was added KOH (1.68 g, 30 mmol). The reaction mixture was stirred at 80 C. for 4 hours. The mixture was cooled to room temperature and poured into ice cold water and the mixture was adjusted to pH 1-2 with 12N hydrochloric acid and stirred at room temperature for 12 hours. The mixture was filtered and solid was washed with water (5 mL) and dried to get the crude product which was purified by column chromatography on silica gel (methanol in dichloromethane, 0.5% v/v) to give 0601-194 (785 mg, 37%) as a yellow solid. LCMS: 214 [M+1]+. 1H-NMR (400 MHz. DMSO-d6) delta 3.51 (s, 2H), 6.76 (d, J=8.0 Hz, 1H), 7.34 (dd, J=8.0, 2.0 Hz, 1H), 7.38 (m, 1H), 10.49 (s, 1H).

According to the analysis of related databases, 87-48-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Curis, Inc.; Bao, Rudi; Lai, Chengjung; Qian, Changgeng; US2013/102595; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

110568-64-4, name is 6-Nitroisoindolin-1-one, 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. category: indolines-derivatives

Toa solution of7D (35 g, 0.2 mol) in MeOH(350 mL) was added Pd/C (7 g), the mixture was stirred at 50¡ãC underH2 at 50 psi for 2 hr.Themixturewas filtered and concentratedin vacuumto afford crude7E (30g) as a white solid.

The synthetic route of 110568-64-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAIKANG (SUZHOU) CO., LTD; HAN, Jie; WO2015/81891; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 114041-16-6, A common heterocyclic compound, 114041-16-6, name is 5,6-Dimethoxyisoindoline, molecular formula is C10H13NO2, 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 13 Preparation of 5,6-dihydroxyisoindoline hydrobromide 3.54 ml of 48% hydrobromic acid was added to 500 mg (2.79 mmol) of 5,6-dimethoxyisoindoline, and the mixture was refluxed for 3 hours under stirring. The precipitated crystals were collected, and washed with ethanol/diethyl ether (1/1) to obtain 520 mg (80.3%) of the above identified compound. The melting point, the infrared absorption spectrum and the 1 H-NHR spectrum of this product were the same as those of the compound of Example 8.

The synthetic route of 114041-16-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Banyu Pharmaceutical Co., Ltd.; US4987235; (1991); A;,
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. 1336963-95-1, name is 6-Bromo-7-fluoroindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C8H3BrFNO2

H202 (10.0 mL, 98 mmol) was added to a solution of 6-bromo-7-fluoroindoline-2,3-dione (5.4 g, 22.13 mmol) and sodium hydroxide (27.7 mL, 55.3 mmol) in water (20 mL) at 0 C and the reaction mixture was stirred at 0 C for 2 hr. The reaction mixture was acidified by 2N HCI until the pH = 6. The solid was collected by filtration and dried in vacuo to give 2-amino-4-bromo-3-fluorobenzoic acid (4.8 g, 20.51 mmol, 93 % yield) as a yellow solid. LCMS: [M+H] 234.1 .

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 1336963-95-1.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; JIN, Qi; POHLHAUS, Denise Teotico; SPLETSTOSER, Jared; (320 pag.)WO2017/98440; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem