Month: November 2020

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 20876-36-2 as follows. 20876-36-2

5-(4-Methoxycarbonylbenzamido)-2-oxindole A mixture of 82.0 mg 5-amino-2-oxindole and 131.0 mg 4-methoxycarbonylbenzoyl chloride in pyridine was stirred at room temperature for 3 hr and poured into ice water.. The precipitate was filtered, washed with water and dried in a vacuum oven to give 138.0 mg of 5-(4-methoxycarbonylbenzamido)-2-oxindole (81percent yield).

According to the analysis of related databases, 20876-36-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sugen, Inc.; US6350754; (2002); B2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 3335-98-6, name is 1-Phenyloxindole, 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. 3335-98-6

General procedure: The mixture of 2,4-dien-1-one (0.5 mmol), indolin-2-one (0.5 mmol, 66.5 mg) and cesium carbonate (0.25 mmol, 81.3 mg) in 3 mL of methylene chloride was stirred at room temperature for 40 min. After the completion monitored by TLC, the solid was filtered, and the liquor was concentrated under reduced pressure. The residue was isolated by column chromatography using petroleum ether and ethyl acetate (v/v 3:1) as eluent to give the pure product. The analytical data for products are given in Tables 1 and 2.

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 3335-98-6.

Reference:
Article; Song, Geyang; Li, Zheng; Chemical Papers; vol. 72; 6; (2018); p. 1379 – 1388;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

181140-34-1, 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 181140-34-1 as follows.

A mixture of 2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione (1) (0.640 g, 3.15 mmol), 2-chloro-4-methoxyphenol (2) (0.500 g, 3.15 mmol), and DBU (25 muL, 0.16 mmol) in p-xylene was heated at 120 C. for throughnight. The reaction mixture was cooled and then propan-2-ol (15 mL) and hydrazine (600 muL, 18.9 mmol) were added. The resulting mixture was heated at 90 C. for 5 h and cooled to room temperature. The reaction was diluted with 1 N NaOH (30 mL) and extracted with ethyl acetate (3¡Á20 mL). The combined extract was washed with 1 N NaOH (25 mL), dried through Na2SO4 and concentrated under reduced pressure to get crude (R)-1-amino-3-(2-chloro-4-methoxyphenoxy)propan-2-ol (3a) (0.547 g) which was used for next reaction without further purification. ESI-MS m/z 232.4 (M++1).

According to the analysis of related databases, 181140-34-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Gregor, Vlad E.; Liu, Yahua; Anikin, Alexey; McGee, Danny Peter Claude; Mikel, Charles; McGrath, Douglas Eric; Vavilala, Goverdhan Reddy; Pickens, Jason C.; Kadushkin, Alexander; Jiang, Luyong; Thiruvazhi, Mohan Santhanam; Zozulya, Sergey; Vairagoundar, Rajendran; Zhu, Tong; Chucholowski, Alexander; Webb, Thomas; Gantla, Vidyasagar Reddy; Yan, Zheng; US2008/171769; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

1168150-46-6, 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. 1168150-46-6, name is (E)-Methyl 3-(methoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

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. 4.1.12.1. Methyl (Z)-3-(((2-((dimethylamino)methyl)benzo[d]oxazol-6-yl)amino)(phenyl)methylene)-2-oxoindoline-6-carboxylate (A1).Yellow solid. Yield: 42%.

The synthetic route of (E)-Methyl 3-(methoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate has been constantly updated, and we look forward to future research findings.

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

52351-75-4, name is 6-Methoxyindoline-2,3-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. 52351-75-4

To a solution of 6-methoxyindoline-2,3-dione (350 mg, 1.976 mmol) in acetonitrile (10 ml), K2CO3 (328 mg, 2.371 mmol) and tert-butyl 2-bromoacetate (350 mul, 2.371 mmol) were added, and the mixture was reacted at room temperature overnight. The insoluble inorganic salts were filtered off and the solvent was evaporated obtaining the crude title compound (550 mg, 1.888 mmol, 96% yield). MS/ESI+ 292.1 [MH]+. The crude was used in the next step without further purification.

Statistics shows that 52351-75-4 is playing an increasingly important role. we look forward to future research findings about 6-Methoxyindoline-2,3-dione.

Reference:
Patent; Chiesi Farmaceutici S.p.A.; ARMANI, Elisabetta; Amari, Gabriele; Capaldi, Carmelida; Carzaniga, Laura; La Porta, Elena; Guala, Matilde; US2013/102576; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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.

Step 1: tert-butyl 5-bromoindoline-l-carboxylateTo a solution of 5-bromoindoline (280 mg, 1.41 mmol) in THF (15 mL) and H20 (5 mL) was added k2C03 (293 mg, 2.12 mmol), followed by di-tert-butyl dicarbonate (617 mg, 2.82 mmol) and the resulting mixture was stirred at room temperature for 2 hours. The mixture was diluted with water and extracted with EtOAc. The combined extract was washed with brine, dried and concentrated to afford desired product (338 mg, 80%). 1H NMR (OMSO-d6): delta 7.59 (1H, br), 7.38 (1H, s), 7.30-7.32 (2H, m), 3.90 (2H, t, / = 8.8 Hz), 3.07 (2H, t, / = 8.8 Hz), 1.50 (9H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 22190-33-6, its application will become more common.

Reference:
Patent; CENTAURUS BIOPHARMA CO., LTD.; XIAO, Dengming; ZHU, Yan; HU, Yuandong; WANG, Huting; LIU, Yuliang; LI, Jijun; SUN, Deguang; WANG, Zhe; WEI, Yongheng; WANG, Zanping; TANG, Guojing; JING, Lutao; WO2012/103806; (2012); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

14192-26-8, A common compound: 14192-26-8, name is Methyl 2-oxoindoline-6-carboxylate, belongs to indolines-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

Example 2: Synthesis of the “chlorimide” ( methyl-1 -(chloroacetyl)-2- oxoindoline-6-carboxylate)6-methoxycarbonyl-2- “chlorimide” oxindol; Method 16-methoxycarbonyl-2-oxindole (400 g; 2,071 mol) is suspended in toluene (1200 ml) at room temperature. Chloroacetic anhydride (540 g; 3,095 mol) is added to this suspension. The mixture is heated to reflux for 3 h, then cooled to 80 0C and methyl cyclohexane (600 ml) is added within 30 min. The resulting suspension is further cooled down to room temperature within 60 min. The mother liquor is separated and the solid is washed with ice cold methanol (400 ml). The crystals are dried to afford 515,5 g (93,5 %) of the “chlorimide” compound as a white solid. 1H-NMR (500 MHz, DMSO-d6) delta: 8,66 (s, 1 H, 6-H); 7,86 (d, J= 8,3 Hz, 1 H, 8-H); 7,52 (d, J = 8,3 Hz, 1 H, 9-H); 4,98 (s, 2 H, 15-H2); 3,95 (s, 3 H, 18-H3); 3,88 (s, 2 H, 3-H2). 13C-NMR (126 MHz, DMSO-d6) delta: 174,7 (C-2); 36,0 (C-3); 131 ,0 (C-4); 140,8 (C-5); 115,7 (C-6); 128,9 (C-7); 126,1 (C-8); 124,6 (C-9); 166,6 (C-10); 165,8 (C-13); 46,1 (C-15); 52,3 (C-18). MS: m/z 268 (M+H)+. Anal, calcd. for Ci2Hi0CINO4: C, 53.85; H, 3.77; Cl, 13.25; N, 5.23. Found: C, 52.18; H, 3.64; Cl, 12.89; N, 5.00.

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, Methyl 2-oxoindoline-6-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; WO2009/71523; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

2058-74-4, Adding a certain compound to certain chemical reactions, such as: 2058-74-4, name is 1-Methylisatin, 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 2058-74-4.

General procedure: The SiO2/g-C3N4 nanocomposite (25 mg) was dispersed in water (3 ml) for 30 min. Indole (2.0 mmol), and isatin (1.0 mmol) were added to the mixture which was stirred for the appropriate time. The progress of the reaction was monitored by thin layer chromatography. After the completion of the reaction, the crude product was extracted with ethyl acetate and dried over anhydrous Na2SO4. Then, the crude product was recrystallized in hot ethanol. The SiO2/g-C3N4 nanocatalyst was recovered from the aqueous layer by centrifuging, washed with EtOH, dried and reused for the next run.

According to the analysis of related databases, 2058-74-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Allahresani, Ali; Nasseri, Mohammad Ali; Nakhaei, Alireza; Research on Chemical Intermediates; vol. 43; 11; (2017); p. 6367 – 6378;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

14192-26-8,Some common heterocyclic compound, 14192-26-8, name is Methyl 2-oxoindoline-6-carboxylate, molecular formula is C10H9NO3, 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.

a) 1,3,3-trimethyl-2-oxoindoline-6-carboxylic acid To a suspension of NaH (60 % on mineral oil, 12.6 g, 314 mmol) in dry THF (260 ml) was added methyl 2-oxoindoline-6-carboxylate (15 g, 78.5 mmol) portionwise during 30 minutes. After gas-evolution ceased Mel (44.5 g, 19.6 ml, 314 mmol) was added dropwise with a syringe- pump during 80 minutes while carefully keeping the temperature between 24 C and 28 C. Thereaction mixture was stuffed for 2 hours at room temperature and then quenched by adding water (5.65 ml, 314 mmol) and then 32 % aqueous NaOH solution (19.6 g, 14.5 ml, 157 mmol) very carefully. The resulting mixture was poured into 100 mL TBME, the layers were separated and the organic layer was extracted with water. The combined aqueous layers were acidified with 25 % aqueous HC1 solution (20m1). The resulting suspension was filtered. The aqueous layer wasback-extracted with dichloromethane, the combined organic layers were dried with sodium sulfate and concentrated in vacuo. The obtained solid was combined with the filtered solid to give the title compound as light red solid (17.7 g).MS ESI (m/z): 220.2 [(M+H)i.1H NMR (DMSO-d6, 300 MHz) oe = 12.98 (br. s, 1H), 7.69 (dd, J=1.0, 7.7 Hz, 1H), 7.55 – 7.41(m, 2H), 3.18 (s, 3H), 1.29 (s, 6H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 2-oxoindoline-6-carboxylate, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BRUNNER, Daniela; HILPERT, Hans; KOLCZEWSKI, Sabine; LIMBERG, Anja; MALBERG, Jessica; PRINSSEN, Eric; RIEMER, Claus; SHANKAR, Bavani G.; STOLL, Theodor; WO2014/202493; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 496-12-8, name is Isoindoline, 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 496-12-8, 496-12-8

(1) Pyridine (6.56 mL, 81.1 mmol) and dimethylaminopyridine (248 mg, 2.03 mmol) were added to a solution of isoindoline (8.08 g, 40.6 mmol) in chloroform (120 mL) at room temperature and the mixture was cooled in ice. Trifluoroacetic acid anhydride (6.77 mL, 48.7 mmol) was added dropwise thereto and the reaction mixture was warmed to room temperature and stirred for 4 hr. The reaction mixture was concentrated under reduced pressure and the residue was diluted with ethyl acetate. The mixture was washed with 1 mol/L hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and brine. The organic layer was dried over anhydrous magnesium sulfate and then the desiccant was filtered off, followed by concentration under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate = 9:1) to afford 1-(1,3-dihydro-2H-isoindol-2-yl)-2,2,2-trifluoroethanone as a brownish red powder (8.66 g).

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, Isoindoline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Taisho Pharmaceutical Co., Ltd.; BUSUJIMA, Tsuyoshi; OI, Takahiro; TANAKA, Hiroaki; SHIRASAKI, Yoshihisa; IWAKIRI, Kanako; SATO, Nagaaki; TOKITA, Shigeru; EP2687507; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem