Author: tianli

A common heterocyclic compound, 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-one, molecular formula is C10H9Cl2NO, 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. 118289-55-7.

General procedure: A mixture of 6-chloro-5-(2-chloroethyl)-1,3-dihydro-2H-indol-2-one 1 (1.00mol), potassium carbonate (1.20mol), secondary amine (2a-h, 1.30mol) in water (10mL) was refluxed until completion (TLC, about 24-48h) and the reaction mass was cooled to RT and then extracted with DCM to get crude 3a-h. Recrystallized using aqueous acetone or aqueous ethanol or methanol (Yield 55-70%).

The synthetic route of 6-Chloro-5-(2-chloroethyl)indolin-2-one has been constantly updated, and we look forward to future research findings.

Reference:
Article; Meti, Gangadhar Y.; Kamble, Atulkumar A.; Kamble, Ravindra R.; Somagond, Shilpa M.; Devarajegowda; Kumari, Sandhya; Kalthur, Guruprasad; Adiga, Satish K.; European Journal of Medicinal Chemistry; vol. 121; (2016); p. 221 – 231;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

1168150-46-6, The chemical industry reduces the impact on the environment during synthesis 1168150-46-6, name is (E)-Methyl 3-(methoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate, I believe this compound will play a more active role in future production and life.

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.

The chemical industry reduces the impact on the environment during synthesis (E)-Methyl 3-(methoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate. I believe this compound will play a more active role in future production and life.

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

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. 99365-40-9

To a stirred mixture of 6-bromoindolin-2-one A.35 (5.0 g, 23.6 mmol) and NaHCO3 (10 eq., 21.0 g) in THF (130 mL) was added (Boc)2O (2.5 eq., 14.0 g) at room temperature under N2. The resulting mixture was heated at reflux for 3 h. After cooling, the mixture was vacuum filtered through a layer of celite and the filter cake was thoroughly washed with THF. The filtrate was concentrated in vacuo and the residue was subjected to combi-flash column chromatography (ethyl acetate/hexanes) to give tert-butyl 6-bromo-2-oxo-2,3-dihydro-lH- indole-1-carboxylate A.36 (6.0 g, 81% yield) as an off-white solid. 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 8.04 (1 H, d, J=I.6 Hz), 7.29 (1 H, dd, J=8.0, 1.8 Hz), 7.1 1 (1 H, d, J=7.8 Hz), 3.60 (2 H, s), 1.65 (9 H, s). LCMS-ESI (POS), M/Z, M+Na+: Found 334.0 and 336.0.

The synthetic route of 99365-40-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; WO2009/158011; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

1914-02-9, A common heterocyclic compound, 1914-02-9, name is 3,3-Dimethylindoline, molecular formula is C10H13N, 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 37 1. Synthesis of intermediate 037-2 The intermediate 001-5 (2.22 g, 14.9 mmol), anhydrous THF (25 mL), 037-1 (1.5 g, 10.2 mmol) and DIPEA (2.58 g, 20.0 mmol) were added into a 100 mL single-necked flask sequentially, and then the reaction was heated to 75C and maintained under stirring for 2.5 h. The reaction was cooled to room temperature, and the reaction mixture was subjected to rotary evaporation, and the crude product was purified through silica gel column chromatography (eluent: EA:PE = 1:15) to give 1.5 g of the intermediate 037-2 (57%) as a white solid. LCMS: 260.1.

The synthetic route of 1914-02-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Shaletech Technology Co., Ltd.; JIANG, Yueheng; (143 pag.)EP3216786; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

2058-72-2, 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 2058-72-2 as follows.

General procedure: A solution of isatins 1 (0.6 mmol), dienones 2 (0.4 mmol) and proline, thioproline or sarcosine(0.8 mmol) in the 10.0 mL of EtOH at reflux for 3 h. After completion of the reaction, as indicated by TLC, the removal of solvent and purification by flash column chromatography (hexane/EtOAc=5:1~3:1) were carried out to furnish the corresponding products 3-5.

According to the analysis of related databases, 5-Bromo-1-methylindoline-2,3-dione, the application of this compound in the production field has become more and more popular.

Reference:
Article; Lin, Bing; Zhou, Gen; Gong, Yi; Wei, Qi-Di; Tian, Min-Yi; Liu, Xiong-Li; Feng, Ting-Ting; Zhou, Ying; Yuan, Wei-Cheng; Molecules; vol. 22; 4; (2017);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

118289-55-7, 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 118289-55-7 as follows.

9. Preparation of ZPR in sulfolane In a three necked flask was charged: BITP HC1 (5.14g, 20mmol), Na2C03 (2.33g, 22mmol), NaI (3g, 20mmol) and sulfolane (20ml). The mixture was heated at 90oC and than CEI (5.29g, 23mmol) was added with more sulfolane (10ml) ; the reaction mixture was maintained at 90C for 4. 5h. The mixture was cooled to the room temperature and THF was added (150ml) ; the solid was filtrated and washed with THF. From the mother liquors a second crop was obtained by precipitation with water. The yield of the two crops is 70% (purity by HPLC 98.4%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 118289-55-7, and friends who are interested can also refer to it.

Reference:
Patent; TEVA PHARMACEUTICAL INDUSTRIES LTD.; TEVA PHARMACEUTICALS USA, INC.; WO2005/40160; (2005); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

3335-98-6, name is 1-Phenyloxindole, 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. 3335-98-6

General procedure: An oven-dried reflux tube equipped with a magnetic stir bar and a Teflon stopcock was charged with aryl halide (1 mmol), oxindole (1 mmol),potassium carbonate (1.1 mmol), catalyst nanoparticles (0.05 mmol)and 1,4-dioxane (2 ml) and heated at 70 C. The mixture was vigorously stirred under these reaction conditions and completion of the reaction was monitored by TLC (EtOAc: n-hexane, 25:75). After completion of the reaction, the reaction mixture was cooled to room temperature, the magnetic nanoparticles of the catalyst were collected using a magnet. Ethyl acetate (5 mL) and water (10 mL)were added to the mixture in the next step. The aqueous layer was furtherextracted by ethyl acetate (2*5 mL). The combined organic layerswere washed with saturated brine, dried over CaCl2, filtered, and concentrated to give a residue which was purified by recrystallization from ethanol and water or by column chromatography on silica gelusing EtOAc: n-hexane, 1:7.

Statistics shows that 3335-98-6 is playing an increasingly important role. we look forward to future research findings about 1-Phenyloxindole.

Reference:
Article; Moghaddam, Firouz Matloubi; Tavakoli, Ghazal; Latifi, Fatemeh; Saeednia, Borna; Catalysis Communications; vol. 75; (2016); p. 37 – 41;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

118289-55-7, A common compound: 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-one, 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.

General procedure: Equimolar mixture of 6-chloro-5-(2-chloroethyl)-1,3-dihydro-2H-indol-2-one 1 (1.00mol) and the carbonyl compound (4i-x) (1.00mol) was stirred at RT in methanol (10mL) for 2h in presence of potassium carbonate (1.20mol). After completion, the reaction mass was filtered to remove inorganic salt, added methanol (10-20mL) and activated charcoal to the filtrate and stirred for 1hr. The crude product was filtered to remove charcoal, methanol was evaporated and cooled to 0-5C to get crude solid. Recrystallized using aqueous ethanol or methanol (Yield 60-70%).

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-Chloro-5-(2-chloroethyl)indolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Meti, Gangadhar Y.; Kamble, Atulkumar A.; Kamble, Ravindra R.; Somagond, Shilpa M.; Devarajegowda; Kumari, Sandhya; Kalthur, Guruprasad; Adiga, Satish K.; European Journal of Medicinal Chemistry; vol. 121; (2016); p. 221 – 231;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

1168150-46-6, name is (E)-Methyl 3-(methoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate, 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. 1168150-46-6

(3) Preparation of methyl (Z)-3-((1-(2-(dimethylamino) acetyl)indolin-5-ylamino)(phenyl)methylene)-2-oxoindoline-6-carboxylate and its hydrochloride1-(2-(dimethylamino) acetyl)-5-aminoindoline (0.082g, 0.3mmol) and methyl (E)-3-(methoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate (0.086g, 0.28mmol) was added to MeOH (2ml). The resulting mixture was heated to 70 C and kept for 7 hours. After being cooled naturally, the mixture was filtered by suction. The filtrate was dried to produce a yellow solid (61mg) in a yield of 35.4%.Methanol (10ml) was added to a concentrated hydrochloric acid (1ml). The above crude product was added to the resulting solution. The mixture was stirred at room temperature for 2 hours, and filtered by suction. The filtrate was dried in vacuum to produce methyl (Z)-3-((1-(2-(dimethylamino) acetyl)indolin-5-ylamino)(phenyl)methylene)-2oxoindoline-6-carboxylate hydrochloride (68mg) as a yellow solid. Formula: C29H28N4O4; MW: 496.2; Mass Spectrum (m/e): 497.3 (M+1) 1H NMR (400MHz; hydrochloride, DMSO-d6, deltappm) ? 12.16 (s, 1H), 10.96 (s, 1H), 9.77 (br. s., 1H), 7.79 (d, J = 8.8 1H), 7.56 (m, 3H), 7.45 (m, 2H), 7.26 (s, 1H), 7.17(m, 1H), 6.88 (s, 1H), 6.74 (s, 1H), 5.81(d, J = 8.4, 1H), 4.25 (m, 2H), 3.96(m, 2H), 3.76 (s, 3H), 3.04 (m, 2H), 2.83 (m, 6H).

Statistics shows that 1168150-46-6 is playing an increasingly important role. we look forward to future research findings about (E)-Methyl 3-(methoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate.

Reference:
Patent; KBP Biosciences Co., Ltd.; LO, Hoyin; WANG, Aichen; ZHANG, Qian; EP2930167; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 15362-40-0, name is 1-(2,6-Dichlorophenyl)-2-indolinone, 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. 15362-40-0

To the four-necked flask was added 668 ml of water and then compound IV (233 g, 0.84 mol), potassium hydroxide (94.3 g,1.68 mol), heated to 100 C for 5 hours, cooled to 60 C to 65 C,Vacuum filter, add a small amount of water, filter cake at 85 CAfter dissolution in water, zinc chloride (229 g, 1.68 mol 1) in water was added, reacted at 85 C for 1 hour,Cooling, filtration was white solid 488.5g (compound I: diclofenac zinc), the yield of 89%

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 15362-40-0.

Reference:
Patent; Jilin University; Liaoyuan Yinying Pharmaceutical Co., Ltd.; Li Guiying; Wang Zhaokun; Li Shumei; Peng Xiaojuan; Jin Xingtong; (8 pag.)CN106905178; (2017); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem