Month: June 2021

Application of 56341-37-8,Some common heterocyclic compound, 56341-37-8, name is 6-Chlorooxindole, molecular formula is C8H6ClNO, 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.

Under argon atmosphere, 3,5-bis(trifluoromethyl)phenylisocyanate(255mg, 1.0mmol) was dissolved in tetrahydrofuran(5mL). A solution of 6-chloro-oxindole(184mg, 1.1mmol) in tetrahydrofuran(5ml) and triethylamine(0.3mL) were added, and the mixture was stirred at room temperature for 4 hours. The reaction mixture was poured into diluted hydrochloric acid and extracted with ethyl acetate. After the organic layer was washed with water and brine, dried over anhydrous magnesium sulfate, the residue obtained by evaporation under reduced pressure was purified by chromatography on silica gel(n-hexane:ethyl acetate=4:1) to give the title compound(172.2mg, 40.7%) as a pink solid.1H-NMR(DMSO-d6): delta 3.97(2H, s), 7.29(1H, dd, J=8.1, 2.1Hz), 7.41(1H, d, J=8.1Hz), 7.88(1H, s), 8.04(1H, d, J=2.1Hz), 8.38(2H, s), 10.93(1H, s).

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

Reference:
Patent; Institute of Medicinal Molecular Design, Inc.; EP1514544; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 2436-29-5, 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. 2436-29-5, name is 3-(1,3-Dioxoisoindolin-2-yl)propanal belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

B] Preparation of compound 1-B; 0.38 g (0.99 mmol) of compound 1-A is dissolved in 15 ml methanol and 0.26 g (1.28 mmol) of 3-(l,3-dioxo-l,3-dihydroisoindol-2-yl)-propionaldehyde, 0.1 ml acetic acid and 0.125 g (1.98 mmol) OfNaBH3CN are added to the solution. The mixture is stirred at 28C for 3.5 hours and the solvent is subsequently evaporated. The crude product is purified by column chromatography on silica gel (petroleum ether(ethyl acetate 10:1 -> 5:1) to give 380 mg (65%) of the desired product as a light yellow solid.

The synthetic route of 3-(1,3-Dioxoisoindolin-2-yl)propanal has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BASILEA PHARMACEUTICA AG; KELLENBERGER, Johannes, Laurenz; DREIER, Juerg; WO2011/18510; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 317-20-4, name is 7-Fluoroisatin, 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. SDS of cas: 317-20-4

Potassium Hydroxide (1.58 g; 28.16 mmol; 3.1 eq.)was added portion wise to a solution of 7-Fluoro-1H-indole-2,3-dione(1.50 g; 9.08 mmol; 1.0 eq.) in acetone (1.0 mL; 13.63 mmol; 1.5 eq.), ethanol (4.50 mL) and water (1.50 mL) in a microwave tube. The reaction was placed in a microwave oven and heated at 100C for 20 min. The reaction mixture was concentrated under vacuum. Water was added followed by a 5N solution of hydrochloric acid until the pH of the solution reached 4. The suspension was then filtered and the solid obtained dried. 8-fluoro-2-methylquinoline-4-carboxylic acid (1.60 g; 85%) was isolated as a brown solid. MS(ES+) m/z 206 (MH+).

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

Reference:
Article; Boiteau, Jean-Guy; Ouvry, Gilles; Arlabosse, Jean-Marie; Astri, Stephanie; Beillard, Audrey; Bhurruth-Alcor, Yushma; Bonnary, Laetitia; Bouix-Peter, Claire; Bouquet, Karine; Bourotte, Marilyne; Cardinaud, Isabelle; Comino, Catherine; Deprez, Benoit; Duvert, Denis; Feret, Angelique; Hacini-Rachinel, Feriel; Harris, Craig S.; Luzy, Anne-Pascale; Mathieu, Arnaud; Millois, Corinne; Orsini, Nicolas; Pascau, Jonathan; Pinto, Artur; Piwnica, David; Polge, Gaelle; Reitz, Arnaud; Reverse, Kevin; Rodeville, Nicolas; Rossio, Patricia; Spiesse, Delphine; Tabet, Samuel; Taquet, Nathalie; Tomas, Loic; Vial, Emmanuel; Hennequin, Laurent F.; Bioorganic and Medicinal Chemistry; vol. 26; 4; (2018); p. 945 – 956;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 3416-57-7, name is 2-(2-Oxopropyl)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 3416-57-7, name: 2-(2-Oxopropyl)isoindoline-1,3-dione

5.5. Examples 5-13; Similar to Examples 3 and 4,5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-ol was prepared using the following solvent/base combinations for the preparation of the 2-amino-4-methyl-1H-pyrrole-3-carboxamide intermediate:

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-(2-Oxopropyl)isoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bednarz, Mark S.; Kanamarlapudi, Ramanaiah C.; Wu, Wenxue; US2008/97098; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 15861-30-0, A common heterocyclic compound, 15861-30-0, name is Indoline-5-carboxylic acid, molecular formula is C9H9NO2, 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.

To a mixture of indoline-5-carboxylic acid (500 mg, 3.07 mmol) in DMF (3 mL) was added Pyridine (0.2 mL) at 0 C followed by acryloyl chloride (555 mg, 6.13 mmol). The reaction mixture was stirred at RT for 5 h. The mixture was then concentrated, DCM was added (20 mL), washed with 0.5N HC1 (10 mL), dried over Na2504, filted and concentrated in vacuo to afford 1- acryloylindoline-5-carboxylic acid (280 mg, 42%) as a yellow solid. [M+H] Calc?d for C12H11N03:218.1; Found: 218.1

The synthetic route of 15861-30-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KINNATE BIOPHARMA INC.; KANOUNI, Toufike; ARNOLD, Lee D.; KALDOR, Stephen W.; MURPHY, Eric A.; TYHONAS, John; (0 pag.)WO2020/6497; (2020); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 611-09-6,Some common heterocyclic compound, 611-09-6, name is 5-Nitroindoline-2,3-dione, molecular formula is C8H4N2O4, 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 isatin 1a (0.147 g, 1 mmol), malononitrile 2a (0.066 g, 1 mmol), and ethyl aceto-acetate 3a (0.13 mL, 1 mmol) was added to a vial containing a magnetic stirring bar and the ionic liquid ([BMIm]BF4, 5 drops). The reaction mixture was sealed and stirred at room temperature until disappearance of the starting materials (under 1 min). At this stage, the product due to poor solubility in the ionic liquid appears as a precipitate. In order to extract the ionic liquid, after completion of the reaction, the residue was washed with 2×10 mL of either water or diethyl ether. Washing the solid residue with ethanol (10 mL, 95.5%) has given remarkably pure powders of product 4a. The ionic liquid was recovered from the aqueous or ethereal extracts by evaporating under reduced pressure and reused in the next cycles.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Nitroindoline-2,3-dione, its application will become more common.

Reference:
Article; Rad-Moghadam, Kurosh; Youseftabar-Miri, Leila; Tetrahedron; vol. 67; 31; (2011); p. 5693 – 5699;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 7477-63-6,Some common heterocyclic compound, 7477-63-6, name is 7-Chloroisatin, molecular formula is C8H4ClNO2, 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: Mg(ClO4)2 (10 mol percent) was added to a mixture of isatin (2 mmol), malononitrile or ethyl cyanoacetate (2mmol), and dimedone (2 mmol) in aqueous ethanol solution(50percent, v/v, 5 mL), and the resulting mixture was stirred at 50°C for 30-60 min. Upon completion of the reaction (TLC),the mixture was allowed to cool to room temperature. The resulting solid was filtered and washed successively with water (2 × 30 mL) and cold aqueous ethanol (2 × 1 mL) to afford pure product 4.

The synthetic route of 7477-63-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wu, Chunlei; Shen, Runpu; Chen, Jianhui; Hu, Chunqi; Bulletin of the Korean Chemical Society; vol. 34; 8; (2013); p. 2431 – 2435;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 6941-75-9, 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 6941-75-9 as follows.

As an example of a synthesis method of core Formula VIi-VIj, 4-bromophthalimide(25) can be treated with a reducing agent (e.g., BF OEt followed by BH THF) in an appropriate solvent (e.g., tetrahydrofuran, THF) for the appropriate length of time at the appropriate temperature, to yield 4-bromoisoindoline, 26. The appropriate temperature and appropriate length of time are determined by referenece to Houben-Weyl 4th Ed. 1952, Methods of Organic Synthesis, Thieme, Volume 21.; 5-bromoisoindoline-l,3-dione (5 g, 22.1 mmol) is dissolved in anhydrous THF (30 ml), treated with BF3 OEt2 (6.667 ml, 132.7 mmol) is added and the reaction was stirred at ambient temperature for 30 minutes. To the reaction mixture 1.0M BH3 THF complex (176.94 ml, 525.3 mmol ) is added and the reaction is heated to 4O0C for 36 h. The progress of the reaction is followed by LC/MS. After completion, the reaction mixture is cooled to ambient temperature and quenched with MeOH (6 ml, drop wise) until the bubbling ceases. Then 2N HCl in water (-40 ml, 80 mmol) are added and the mixture is refluxed for 3 h. The reaction is then cooled to ambient temperature and is washed with diethyl ether (2 x 40 ml). The water layer is brought to pH 14 with 6N NaOH (aq) and extracted with ethyl acetate (3 x 100 ml). The combined organic extracts are dried over anhydrous Na2Stheta4 and solvent is removed under reduced pressure to yield 5-bromoisoindoline (68%), (m/z 413[MH+]).

According to the analysis of related databases, 6941-75-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2007/38459; (2007); A2;,
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. 60434-13-1, name is 5-Chloro-1-methylindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C9H6ClNO2

A mixture of 2- (1-benzyl-2-oxoindol-3-yl) acetic acid67.4 mg (0.24 mmol),5-chloro-1-methyl isatin 39 mg (0.2 mmol)N, N’-2- (7-benzo benzotriazole) -N, N, N ‘, N’-tetramethyluronium hexafluorophosphate (106.4 mg, 0.28 mmol)Triethylamine 50.6 mg (0.5 mmol)And 2 mL of tetrahydrofuran were placed in a 25 mL two-necked flask,Reaction at 0 C for 6 h,The reaction solution was concentrated,Eluting with a mixed solvent of petroleum ether: ethyl acetate ratio of 3: 1 as elution column,Collecting the eluted fraction of all the products detected,The solvent was removed by rotary distillation to give 82.4 mg of product,The yield was 90% and the Dr value was 4: 1.

The synthetic route of 60434-13-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; China Pharmaceutical University; Du Ding; Cao Jing; Dong Shuding; (14 pag.)CN106749295; (2017); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

1074-82-4, name is Potassium 1,3-dioxoisoindolin-2-ide, 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

a) Preparation of 5-bromopentylphthalimide Potassium phthalimide (5.4 mmoles) was added to a solution of 1,5-dibromopentane (3.72 g; 16.2 mmoles) in dimethylformamide (8 ml) and heated to 80C approx. under stirring. After 2 hours, water was added and the solution was repeatedly extracted with ether. The collected organic phases were washed with water, dried on Na2SO4 and evaporated under reduced pressure to give a solid (4.50 g), which was purified by chromatography on silica gel (Etp/Et2O 8:2) yielding 2.38 g of a white solid. Yield 68%.

The synthetic route of 1074-82-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEDIOLANUM FARMACEUTICI S.P.A.; EP575954; (1993); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem