Month: July 2021

Reference of 15362-40-0, The chemical industry reduces the impact on the environment during synthesis 15362-40-0, name is 1-(2,6-Dichlorophenyl)-2-indolinone, I believe this compound will play a more active role in future production and life.

Pyrrole-2-carboxaldehyde (1 mmol) was treated with benzyl bromide (1.5 mmol) in the presence of NaH (1.5 mmol) in DMF (solvent) at 0 C for 15 min, the progress of the reaction was monitored with TLC and the reaction was shifted to room temp for another 15 min. After completion, the reaction was quenched by adding water and the crude product was isolated by extraction with ethyl acetate (2 x 50 ml), the organic layers were combined, dried over Na2SO4 and distilled in vacuum to give N-benzylpyrrole-2-carboxaldehyde (A) which was further purified by column chromatography using ethyl acetate: hexane (1:50). N-benzylpyrrole-2-carboxaldehyde (A, 1 mmol) was reacted with 1-(2,6-dichlorophenyl)-2-indolinone (1.2 mmol) in the presence of piperidine (0.2 mmol) in CHCl3/ DMF under microwave irradiations at 100 C for 1h. The progress of the reaction was monitored with TLC. After completion, the reaction was worked up by adding water and extraction with chloroform (2 x 50 ml). Combined organic layers were dried over Na2SO4 and distilled in vacuum to give crude product 3a which was purified by column chromatography using ethyl acetate:hexane (3:50) as eluent. Yellow Solid, yield 62%, mp 153-155 C; IR (KBr): 3059, 2925, 1695, 1599, 1485, 1365; 1H NMR (500 MHz, CDCl3, 25 C, TMS) delta: 5.41 (s, 2H, CH2), 6.40-6.41 (m, 2H, ArH), 7.04 (t, 1H, J = 7.5 Hz, ArH), 7.07 (s, 1H, ArH), 7.13 (t, 1H, J = 7.6 Hz, ArH), 7.19 (d, 2H, J = 7.4 Hz, ArH), 7.29-7.34 (m, 2H, ArH), 7.36-7.41 (m, 3H, ArH), 7.47 (s, 1H, =CH), 7.52 (d, 2H, J = 8.09 Hz, ArH), 8.49 (dd, 1H, J = 4.13 Hz, 1.29 Hz, ArH); 13C NMR (125 MHz, CDCl3, normal/DEPT-135) delta: 51.3 (-ve, CH2), 108.6 (+ve, CH), 110.7, (+ve, CH), 117.1 (ArC), 117.8 (+ve,CH), 121.9 (+ve, CH), 122.1 (+ve, CH), 123.0 (+ve, CH), 125.2 (ArC), 126.2 (+ve, CH), 126.9 (+ve, CH), 127.1 (+ve, CH), 128.0 (+ve, CH), 128.7 (ArC), 128.8 (+ve, CH), 128.9 (+ve, CH), 129.1 (+ve, CH), 129.2 (+ve, CH), 130.1 (+ve, CH), 131.4 (ArC), 135.9 (ArC), 137.3 (ArC), 139.2 (ArC), 164.8 (C=O); HRMS (ESI) m/z for C26H18Cl2N2O [M+H]+ calcd. 445.0868, found 445.0817.

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, 1-(2,6-Dichlorophenyl)-2-indolinone, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kaur, Jagroop; Kaur, Baljit; Singh, Palwinder; Bioorganic and Medicinal Chemistry Letters; vol. 28; 2; (2018); p. 129 – 133;,
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. 20780-72-7, name is 4-Bromoisatin, This compound has unique chemical properties. The synthetic route is as follows., Safety of 4-Bromoisatin

A mixture ofZn power (8.64g, 132.13mmol) and TiCl4 (12.60g, 66.42mmol) in THF (100mL) was stirred at 80 C for 2 hours, then it was cooled to RT, a solution of 4-bromoindoline-2, 3-dione (5.01g, 22.16mmol) in THF (100mL) was added dropwise under N2. After completion of the reaction, Hydrochloric acid solution (100mL, 3M) was added, the mixture was extracted with DCM (50mL3), the organic phase was washed with brine (50mL2), dried over anhydrous Na2SO4, filtered and the solvent was removed under reduced pressure, the residue was purified by column chromatography to afford the compound 9a (2.63g, 56.0%). MS: 212 (M+H) +.

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 20780-72-7.

Reference:
Patent; JACOBIO PHARMACEUTICALS CO., LTD.; MA, Cunbo; GAO, Panliang; CHU, Jie; WU, Xinping; WEN, Chunwei; KANG, Di; BAI, Jinlong; PEI, Xiaoyan; (82 pag.)WO2017/211303; (2017); 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. 6326-79-0, name is 6-Bromoisatin, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H4BrNO2

The 1.15g (5mmol) 6- bromo-isatin was dissolved in 10mL DMF,1.03 g (7.5 mmol) of potassium carbonate was added with stirring.Then, 0.804 g (6.25 mmol) of dimethyl sulfate was added dropwise, and the mixture was reacted at room temperature for 4 hours, and the mixture was poured into 100 mL of ice water.The extract was extracted with ethyl acetate (60 mL×3), and the organic layer was evaporated.After concentrated to dryness, it was purified by silica gel column chromatography ( petroleum ether: ethyl acetate = 20:3)0.753 g of a red solid was obtained in a yield of 63%.

The synthetic route of 6326-79-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shandong University; Li Xun; Yu Haipeng; Zheng Yongtang; Huang Xusheng; (15 pag.)CN110183372; (2019); A;,
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. 99365-40-9, name is 6-Bromoindolin-2-one, A new synthetic method of this compound is introduced below., Recommanded Product: 6-Bromoindolin-2-one

4 mmol of 6-bromo-2-indolone (XI) was dissolved in 20 ml of tetrahydrofuran solution, 4.8 m mol of sodium hydrogencarbonate was added, and then 8 mmol of di-tert-butyl dicarbonate was added, and the reaction system was stirred at 66 C. The reaction was quenched with TLC until the title material was evaporated. The mixture was evaporated to ethyl ether. Separation and purification with n-hexane:ethyl acetate = 5:1 as eluent gave 668 mg of white solid.The yield was 54%.

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; UNIV GUANGDONG TECHNOLOGY; Guangdong University of Technology; ZHUANG GUISHENG; Zhuang Guisheng; LIU YAN; Liu Yan; LU HANBIN; Lu Hanbin; HE HONGYUN; He Hongyun; MARUOKA HIROJI; Wan Gangqier; (32 pag.)CN108299491; (2018); A;,
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. 667463-64-1, name is 6-Bromo-1-methylindoline-2,3-dione, A new synthetic method of this compound is introduced below., Formula: C9H6BrNO2

1-3.1 (397 mg, 1.65 mmol) and hydrazine hydrate (1 mL, 20.6 mmol) are heated to 100 C for 1 h and at 125 C for 1 h. To the cool reaction mixture DCM and water are added and the aqueous layer extracted twice with DCM. The combined organic layers are washed with brine, dried, concentrated and the residue purified via column chromatography (using solvent mixture cyclohexane / EA = 3:1). Yield 65%. m/z 226 [M+H]+, m/z 224 [M+H]-, rt 0.58 min, LC-MS Method b.

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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GRUNDL, Marc; OOST, Thorsten; PAUTSCH, Alexander; PETERS, Stefan; RIETHER, Doris; WIENEN, Wolfgang; WO2013/41497; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 6326-79-0, name is 6-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 6326-79-0, Computed Properties of C8H4BrNO2

To R27 (25.0 g, 111 mmol) in acetonitrile (750 mL) is added MeI (15 mL, 241 mmol) and K2CO3 (60.0 g, 434 mmol) and the reaction mixture is stirred at 60 C. for 2 h. The reaction mixture is filtered and concentrated. Water and ethyl acetate are added to the residue. The organic layer is extracted twice with water, dried over MgSO4 and concentrated. Yield 56%, m/z 240/242 [M+H]+, rt 0.48 min, LC-MS Method X001-004.

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

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ANDERSKEWITZ, Ralf; BINDER, Florian; GRAUERT, Matthias; GRUNDL, Marc; HAEBEL, Peter Wilhelm; OOST, Thorsten; PAUTSCH, Alexander; PETERS, Stefan; VINTONYAK, Viktor; US2014/275025; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

65826-95-1, name is 5-Methylindoline, 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. Application In Synthesis of 5-Methylindoline

General procedure: In a 2-neck RBF, 1 (20 mg, 0.0005 mmol) and TMNO (45 mg, 0.6 mmol) were suspended in toluene (4 mL) and to this solution indoline (60 mg, 0.5 mmol) was added. The reaction mixture was then heated to 100 oC for 20 h and it was filtered and solvent evaporated. The crude product obtained was purified by column chromatography using hexane/ethylacetate (7:1) as eluent to give pure indole (47 mg, 79%). A similar procedure was used for the other indolines and N-heterocycles.

The synthetic route of 65826-95-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kumaran, Elumalai; Leong, Weng Kee; Tetrahedron Letters; vol. 59; 44; (2018); p. 3958 – 3960;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 56341-37-8, 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. 56341-37-8, name is 6-Chlorooxindole, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 11 (FROM TABLE 3) 3-[5-(6-Chloro-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-4-methyl-1H-pyrrol-3-yl]-propionic acid 4-(2-Carboxyethyl)-2-formyl-3-methylpyrrole (200 mg), 167.6 mg 6-chloro-2-oxindole, and 166 muL piperidine in 2 mL of ethanol were heated at 95 C. for 5 hours. The reaction mixture was cooled and concentrated. The residue was suspended in 6 N aqueous hydrochloric acid. The precipitate was filtered, washed with water to pH 6 and dried in a vacuum oven to give 246 mg (74%) of the title compound as a brown solid. 1H-NMR (360 MHz, DMSO-d6): delta 13.22 (s, br, 1H, NH-1′), 12.09 (s, br, 1H, COOH), 10.95 (s, br, 1H, NH-1), 7.78 (d, J=7.95 Hz, 1H, H-4), 7.66 (s, 1H, H-vinyl), 7.18 (d, J=2.64 Hz, 1H, H-2′), 7.01 (dd, J=1.90, 7.95 Hz, 1H, H-5), 6.86 (d, J=1.90 Hz, 1H, H-7), 2.65 (t, J=7.14 Hz, 2H, CH2CH2COOH), 2.45 (t, J=7.14 Hz, 2H, CH2CH2COOH), 2.26 (s, 3H, CH3).

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

Reference:
Patent; Sugen, Inc.; US6878733; (2005); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 317-20-4, 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.

Potassium hydroxide (1.58 g; 28.16 mmol; 3.10 eq.) was added portion wise to a solution of 7-Fluoro-1H-indole-2,3-dione (1.50 g; 9.08 mmol; 1.00 eq.) in acetone (1.00 ml; 13.63 mmol; 1.50 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 100 C. 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; 85.84%) was isolated as a brown solid

Statistics shows that 7-Fluoroisatin is playing an increasingly important role. we look forward to future research findings about 317-20-4.

Reference:
Patent; GALDERMA RESEARCH & DEVELOPMENT; OUVRY, Gilles; HARRIS, Craig Steven; BHURRUTH-ALCOR, Yushma; (65 pag.)US2017/247353; (2017); A1;,
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. 496-12-8, name is Isoindoline, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of Isoindoline

General procedure: Naphthylboronic acid (0.25 g, 1.5 mmol) was added with 0.094 g of phenol (1.0 mmol) to 15 mL of DCM. Copper(II) acetate (0.36 g, 2.0 mmol) was then added along with triethylamine (0.5g, 5.0 mmol), and the dismembrator horn placed in the reaction vessel. The sonicator was set to 55 watts and the reaction was allowed to proceed for 4 hours (1 minute pulse with a 3 second rest). Post reaction, the product was isolated by column chromatography. Product yields were determined by weight and purity was confirmed by GC/MS and NMR.

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 496-12-8.

Reference:
Article; Musolino, Bryan J.; Kabalka, George W.; Heterocycles; vol. 90; 1; (2015); p. 271 – 297;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem