Month: July 2021

19727-83-4, name is 6-Nitroindoline, 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. Safety of 6-Nitroindoline

To a stirred solution of 6-nitroindoline (8.0 g, 48.8 mmol) in DCM (50 ml_) was added pyridine (9.9 ml_, 122 mmol), (Boc)2O (10.6g, 48.6 mmol) and catalytic DMAP. EPO The mixture was stirred overnight. Reaction was washed with brine, and the organic layer was dried (Na2SO4), filtered and concentrated. Chromatography (20% EtOAc/hexanes) provided 1-Boc-6-nitroindoline (10 g, 78%).

The synthetic route of 19727-83-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; PHARMACOPEIA DRUG DISCOVERY, INC.; WO2007/24944; (2007); A1;,
Indoline – Wikipedia,
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Synthetic Route of 56341-39-0, 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. 56341-39-0 name is 6-Fluoroindolin-2-one, 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.

EXAMPLE 14 A solution of 6-fluorooxindole (227 mg, 1.5 mmol), (prepared according to Synthesis 1993, 51), in THF (3 ml) was added dropwise under nitrogen to sodium hydride (42 mg, 1.75 mmol, pre-washed with hexane). After stirring the resulting mixture for 20 minutes at ambient temperature, 4-chloro-6-methoxy-7-(3-morpholinopropoxy)quinazoline (169 mg, 0.5 mmol), (prepared as described for the starting material in Example 5), was added as a solid, followed by DMF (3 ml). The mixture was then heated at 75 C. for 1 hour, allowed to cool and the solvent removed by evaporation The mixture was partitioned between water and ether. The aqueous layer was separated and adjusted to pH8 with 2M hydrochloric acid and then extracted with ethyl acetate. The organic layer was washed with brine, dried and volatiles removed by evaporation. The residue was triturated with ether and collected by filtration. This solid was dissolved in methylene chloride/methanol, a 5M solution of hydrogen chloride in isopropanol (0.5 ml) was added and the volatiles removed by evaporation. The resulting solid was collected by filtration, washed with ether and dried under vacuum to give 4-(6-fluorooxindol-3-yl)-6-methoxy-7-(3-morpholinopropoxy)quinazoline hydrochloride (198 mg, 81%) as a yellow solid. m.p..195-200 C. 1H NMR Spectrum: (DMSOd6, CF3CO2D) 2.25-2.4(m, 2H); 3.05-3.2(m, 2H); 3.25-3.35(m, 2H); 3.52(d, 2H); 3.72-3.85(m, 2H); 3.9(s, 3H); 4.05(d, 2H); 4.3(t, 2H); 6.8-6.9(m, 2H); 7.32(s, 1H); 7.62-7.7(m, 1H); 7.78(s, 1H); 8.7-8.8(m, 1H).

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

Reference:
Patent; Zeneca Limited; US6265411; (2001); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 22190-33-6,Some common heterocyclic compound, 22190-33-6, name is 5-Bromoindoline, molecular formula is C8H8BrN, 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 stirred solution of 5-bromo-indoline (3.0 g, 15 mmol) in acetonitrile (100 ml), was added DMAP (0.185 g, 1.522 mmol) and di-tert-butyl dicarbonate (3.98 g, 18.3 mmol) and the reaction was stirred at ambient temperature for 16 h. The reaction mixture was concentrated on reduced pressure to obtain a residue which was diluted with diethyl ether and washed with water and brine solution (2×). The combined ether layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford the crude product as an off-white solid, which was used in the next step without further purification (3.0 g).

The synthetic route of 22190-33-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dow AgroSciences LLC; Lo, William C.; Hunter, James E.; Watson, Gerald B.; Patny, Akshay; Iyer, Pravin S.; Boruwa, Joshodeep; US2014/171308; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 99365-40-9, 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. 99365-40-9, name is 6-Bromoindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a 25 mL round bottomed flask was added different substituted oxindoles 8 (0.2 mmol, 1.0 equiv.) and bromoethylsulfonium salt 9 (132.99 mg, 0.3 mmol, 1.5 equiv.), DMF (2 mL). The mixture was stirred at room temperature for 5min and Et3N (61.88 mg, 0.6 mmol, 3.0 equiv.) was added into reaction system. The mixture was stirred for 6h at room temperature until the reaction completed, quenched with saturated ammonium chloride solution (5 mL), and was extracted with EtOAc (3×30 mL). The combined organic layer washed with H2O (2×10 mL), dried with anhydrous sodium sulfate. After concentration, product was purified using column chromatography on silica gel with suitable eluent.

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-Bromoindolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Qin, Hui; Miao, Yuanyuan; Zhang, Ke; Xu, Jian; Sun, Haopeng; Liu, Wenyuan; Feng, Feng; Qu, Wei; Tetrahedron; vol. 74; 47; (2018); p. 6809 – 6814;,
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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. 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, A new synthetic method of this compound is introduced below., Safety of 2-Oxoindoline-5-carboxylic Acid

General procedure: Aldehydes (1-5) (0.2 mmol) and oxindoles (7-11) (0.2 mmol) were dissolved in alcohol MeOH, EtOH, or tert-BuOH (1.5 ml). 3 droplets of piperidine were added to the solvents and the reaction mixture was stirred in a sealed vial at 60 – 70 C for 2 – 8 hours.

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; Nemes, Zoltan; Takacs-Novak, Krisztina; Voelgyi, Gergely; Valko, Klara; Beni, Szabolcs; Horvath, Zoltan; Szokol, Balint; Breza, Nora; Dobos, Judit; Szantai-Kis, Csaba; Illyes, Eszter; Boros, Sandor; Kok, Robbert Jan; ?rfi, Laszlo; Bioorganic and Medicinal Chemistry Letters; vol. 28; 14; (2018); p. 2391 – 2398;,
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. 1168150-46-6, name is (E)-Methyl 3-(methoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of (E)-Methyl 3-(methoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate

General procedure: A mixture of intermediate (3a, 3b, 6a, 6b, 10a, 10b, 11a-d, and14a-g, 1.5 mmol) and methyl (E)-3-(methoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate (1.5 mmol) in methanol (10 mL) wasstirred under reflux for 5-10 h. When TLC showed the completionof the reaction, the solution was cooled to room temperature. Theprecipitate was filtered off to give a crude product, which wasrecrystallized from methanol to provide the target compounds.

According to the analysis of related databases, 1168150-46-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Qin, Mingze; Tian, Ye; Sun, Xiaoqing; Yu, Simiao; Xia, Juanjuan; Gong, Ping; Zhang, Haotian; Zhao, Yanfang; European Journal of Medicinal Chemistry; vol. 139; (2017); p. 492 – 502;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 675109-26-9, 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. 675109-26-9 name is 6-Bromoisoindolin-1-one, 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 mixture of 78 6-bromoisoindolin-1-one (5.0 g, 23.58 mmol), 176 Pd(AcO)2 (528 mg, 2.30 mmol), Xantphos (1.36 g, 2.36 mmol) and 177 TEA (1.19 g, 117.9 mmol) in 170 methanol (100 mL) was heated to 70 C. under 1 atm of 178 CO (gas) overnight. The reaction mixture was filtered and the filtrate was concentrated under vacuum. The residue was purified by silica column chromatography (1%-2% 23 MeOH in 31 DCM) to give 72A (500 mg, 11% yield) as a white 179 solid: ESI m/z 192.1 [M+H]+ .

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Bromoisoindolin-1-one, and friends who are interested can also refer to it.

Reference:
Patent; Seal Rock Therapeutics, Inc.; BROWN, Samuel David; US2018/291002; (2018); 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. 141452-01-9, name is Methyl indoline-5-carboxylate, A new synthetic method of this compound is introduced below., category: indolines-derivatives

In a 100 mL single-mouth bottle, dihydroindole-5-carboxylic acid methyl ester (800 mg, 4.50 mmol) was added and methanol was added.(15 mL) was dissolved, followed by the addition of potassium hydroxide (760 mg, 13.5 mmol), and reacted at 45 C for 15 h. After the reaction was completed,Dilute with 100 mL of water, then adjust the pH to 2 with 2M diluted hydrochloric acid, and use dichloromethane (50 mL×3).Drying and spinning off the solvent gave the title compound.

The synthetic route of 141452-01-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nanjing Shenghe Pharmaceutical Co., Ltd.; Wang Yong; Zhao Liwen; Ge Chongxun; Huang Yiqiang; Cao Chen; Li Qingqing; Hou Shaohua; (63 pag.)CN108276382; (2018); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 552330-86-6, name is 5-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. Product Details of 552330-86-6

Toa solution of6F (6 g, 28 mmol)in MeOH(IOO mL), palladium acetate (0.12g), Et3N (8.6 g, 85 mmol) and Xantphos (0.6g) were added. The reactionmixturewas stirredat 140 C under CO (3 MPa)overnight.Themixturewas cooled to room temperature and filtered.The filtrate was concentrated in vacuum to provide 6G (6 g). 1H-NMR (400 MHz, DMSO_d6): 8.82-8.84 (s,IH),8.16-8.18 (s,IH), 8.05-8.07(s, IH), 7.79-7.8l(s,IH), 4.44-4.46 (s, 2H), 3.90-3.92 (s, 3H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 552330-86-6, its application will become more common.

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

Synthetic Route of 1254319-51-1,Some common heterocyclic compound, 1254319-51-1, name is 6-Bromo-2-methylisoindolin-1-one, molecular formula is C9H8BrNO, 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 solution of 6-bromo-2-methylisoindolin-1-one (5 g,22.1 mmol) in dmf (30 mL) was added bis(pinacolato)diboron (6.18 g,24.3 mmol) and potassium acetate (6.51 g,66.4 mmol). The reaction mixture was degassed and backfilled with N2 gas,and 1,1 ?-bis(diphenylphosphino)fenocene palladium(II)dichloride dichloromethane (0.903 g,1.106 mmol) was added.The reaction mixture was stined at 80 C for 10 hours. After diluting with EtOAc and water, The organic layer was concentrated and purified on silica column (100% EtOAc) to get the product as a mixture of the title compound as a boronic ester and boronic acid,which was not further purified.MS: 274 (m+1)?H NMR (500 MHz,CDCl3): oe 8.33 (s,1H),7.98 (d,7.5 Hz,1H),7.46 (d,7.5 Hz,1H),4.41 (s,2H),3.22 (s,3H),1.38 (s,12H). The following intermediates in table c were preparedaccording to scheme c using the procedure outlined in the synthesis intermediate cl using 1,1?-bis(di-tert-butylphosphino)fenocene palladium dichloride or 1,1 ?-bis(diphenylphosphino)ferrocene palladium(II)dichloride dichloromethane complex as the palladium catalyst with toluene or dmf as the reaction solvent. The starting material bromide was either commercially available,known in the literature,or prepared using the protocol in scheme B.

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-2-methylisoindolin-1-one, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MSD R&D (CHINA) CO., LTD.; ACTON, John J.; BAO, Jianming; EGBERTSON, Melissa; GAO, Xiaolei; HARRISON, Scott Timothy; KNOWLES, Sandra Lee; LI, Chunsing; LO, Michael Man-Chu; MAZZOLA, Robert D., Jr.; MENG, Zhaoyang; RUDD, Michael T.; SELYUTIN, Oleg; TELLERS, David M.; TONG, Ling; WAI, Jenny Miu-Chun; (125 pag.)WO2017/107089; (2017); A1;,
Indoline – Wikipedia,
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