Category: indolines-derivatives

Application of 1127-59-9, The chemical industry reduces the impact on the environment during synthesis 1127-59-9, name is 7-Methylindoline-2,3-dione, I believe this compound will play a more active role in future production and life.

General procedure: A mixture of 1H-pyrazol-5-amin (1 mmol), isatin (1 mmol) and enolizable C ? H activated compound (1 mmol) in NDDES (1.5 ml)was stirred under microwave irradiation at 60°C for an appropriate time. The progress of the reaction was monitored by TLC. After completion of the reaction, the mixture was cooled to room temperature and cold water was added to the reaction mixture. The precipitated solid was isolated by filtration, washed with water and purified by recrystallization from ethanol.

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, 7-Methylindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zhang, Wei-Hong; Chen, Meng-Nan; Hao, Yi; Jiang, Xin; Zhou, Xiao-Lin; Zhang, Zhan-Hui; Journal of Molecular Liquids; vol. 278; (2019); p. 124 – 129;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 675109-26-9,Some common heterocyclic compound, 675109-26-9, name is 6-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.

General procedure: 5-Bromo-2-methylisoindolin-1-one (520 mg, 2.30 mmol) and thiophene-2-boronic acid (442mg, 3.45 mmol) were dissolved in a mixure of toluene (12 mL) and EtOH (6 mL). A solutionof 2 M Na2CO3 (3 mL) and Pd(dppf)Cl2 (94 mg, 0.12 mmol) were added and the entiremixture heated at reflux under N2 for 2 h. Additional thiophene-2-boronic acid (294 mg, 2.30mmol) was added and reflux continued under N2 overnight. Upon cooling, the mixture wasdiluted with water (100 mL) and extracted with CH2Cl2 (6×50 mL). The combined organicfractions were dried (Na2SO4), filtered, and the solvent removed under reduced pressure togive a crude solid which was purified by flash column chromatography on silica gel (EtOAcas eluant). The title compound was isolated as a light-brown solid (510 mg, 97%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Bromoisoindolin-1-one, its application will become more common.

Reference:
Article; Spicer, Julie A.; Miller, Christian K.; O’Connor, Patrick D.; Jose, Jiney; Huttunen, Kristiina M.; Jaiswal, Jagdish K.; Denny, William A.; Akhlaghi, Hedieh; Browne, Kylie A.; Trapani, Joseph A.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 4; (2017); p. 1050 – 1054;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 59-48-3,Some common heterocyclic compound, 59-48-3, name is Indolin-2-one, molecular formula is C8H7NO, 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.

5-(Bromo)-1,3-dihydro-indol-2-one. A solution of oxindole (2.0 g, 15.0 mmol) and sodium acetate (2.1 g, 25.5 mmol) in CHCl3 (20 cm3) was treated with bromine (2.4 g, 15.0 mmol) in CHCl3 (10 cm3). After 30 min. the mixture was allowed to warm to room temperature (RT) and stirred for 1 hour. The reaction mixture was diluted with EtOAc (500 cm3) and poured into water. The aqueous layer was extracted with EtOAc (*2), the combined organic layers were washed with water, sat. sodium hydrogen carbonate solution, brine, dried (MgSO4), and evaporated to give the title compound (3.1 g, 14.6 mmol, 96%) as an off-white solid which was used without further purification: mp. 221-223 C.; 1H NMR (DMSO-d6) delta 3.51 (s, 2H), 6.76 (d, 1H, J=8.1 Hz), 7.33(dd, 1H, J=8.1, 1.7 Hz), 7.37 (s, 1H), 10.49 (br s, 1H); 13C NMR (DMSO-d6) delta 36.10 (t), 111.21 (d), 113.16 (s), 127.54 (d), 128.3 (s), 130.40 (d), 143.34 (s), 176.24 (s); MS (EI) m/z 211, 213 (M)+.

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

Reference:
Patent; Wyeth; Ligand Pharmaceuticals, Inc.; US6462032; (2002); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 118289-55-7,Some common heterocyclic compound, 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-one, molecular formula is C10H9Cl2NO, 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: 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%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Chloro-5-(2-chloroethyl)indolin-2-one, its application will become more common.

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

Electric Literature of 205383-87-5, 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. 205383-87-5 name is tert-Butyl 2-oxospiro[indoline-3,3′-pyrrolidine]-1′-carboxylate, 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.

Step A: tert-butyl 5 -chloro-2-oxospiro [indoline-3 ,3 ?-pyrrolidinel- 1 ?-carboxylateTo a stirred solution tert-butyl 2-oxospiro[indoline-3,3?-pyrrolidine]-i?-carboxylate (800 mg,2.77 mmol) in dichioromethane (40 mL) and DMF (4 mL) was added N-chlorosuccinimide and the mixture was allowed to stir at room temperature overnight. Aqueous NaHCO3 was added and the mixture was extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated. The crude product was purified by ISCO (40g, EtOAc/Hex= 1 / 1) to give tert-butyl 5 -chloro-2-oxospiro [indoline-3 ,3 ?-pyrrolidine]- 1 ?-carboxylate. [M+ 1] =324.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl 2-oxospiro[indoline-3,3′-pyrrolidine]-1′-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIM, Yeon-Hee; GUO, Zhuyan; ALI, Amjad; EDMONDSON, Scott, D.; LIU, Weiguo; GALLO-ETIENNE, Gioconda, V.; WU, Heping; GAO, Ying-Duo; STAMFORD, Andrew, M.; YU, Younong; KEVIN, Nancy, J.; ANAND, Rajan; SHA, Deyou; NEELAMKAVIL, Santhosh, F.; HUSSAIN, Zahid; KUMAR, Puneet; MONINGKA, Remond; DUFFY, Joseph, L.; XU, Jiayi; JIANG, Yu; SONE, Hiroki; CHAKRABARTI, Anjan; (183 pag.)WO2015/164308; (2015); 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. 7477-63-6, name is 7-Chloroisatin, A new synthetic method of this compound is introduced below., Computed Properties of C8H4ClNO2

General procedure: The mixture of isatin (1 mmol), 3-amino-1-phenyl-1H-pyrazol-5(4H)-one (1 mmol), 1,2-diarylethan-1-one, 2,3-dihydroinden-1-one (1 mmol) or 3,4-dihydronaphthalen-1(2H)-one (1 mmol), H2O (6 mL), HOAc (2 mL) was put in a reaction flask under 90 °C about 5-7 h (monitored by TLC). After completion, the reaction mixture was cooled to room temperature and the products would be isolated out at same time. Then, compound 4 was recrystallized from DMF, however, the pure products of 6 and 8 were filtered from water, dried, without further recrystallization.

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; Wang, Zhansheng; Gao, Lingli; Xu, Zhongyun; Ling, Zhi; Qin, Yaqi; Rong, Liangce; Tu, Shu-Jiang; Tetrahedron; vol. 73; 4; (2017); p. 385 – 394;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 17826-05-0, name is 5,6-Dibromoindoline-2,3-dione, 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. Application In Synthesis of 5,6-Dibromoindoline-2,3-dione

General procedure: Water (15 mL) was added to a mixture of 1.0 mmol of isatin derivative, 1.2 mmol of creatinine (for 2p, 2.3 mmol of creatinine) and 1 mol% of HAuCl4 and the resulting suspension was heated to reflux for 30 min. The clear reaction mixture was cooled to 15-20 C. The precipitated aldol product was filtered and washed with copious amount of water and then with methanol and ethyl acetate (EtOAc). The obtained product was thoroughly dried under vacuum to afford the pure product 2a-2p.

The synthetic route of 5,6-Dibromoindoline-2,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Parthasarathy; Ponpandian; Praveen; Cuihua Xuebao/Chinese Journal of Catalysis; vol. 38; 5; (2017); p. 775 – 783;,
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., COA of Formula: C10H11NO2

To a solution of 4,6-dichloropyrimidine (815 mg, 4.60 mmol) in n-propanol (12.0 ml.) was added 2,3-dihydro-1 H-indole-5-carboxylic acid methyl ester (Bioorg. Med. Chem. Lett. 2008, 18, 5684 – 8) (754 mg, 5.06 mmol). The resulting yellow solution was heated to reflux for 2 hours. After allowing the reaction to cool to room temperature, the reaction mixture was diluted with methyl te/t-butyl ether and then filtered. The collected solids were partitioned between chloroform and saturated aqueous sodium bicarbonate solution. The separated organic phase was dried over magnesium sulfate, filtered, and the filtrate concentrated under reduced pressure to afford 1-(6-chloro-pyrimidin-4-yl)- 2,3-dihydro-1 H-indole-5-carboxylic acid methyl ester (929 mg, 69.7 %) as an off-white solid. 1H NMR (400 MHz, deuterochloroform) delta 3.32 (t, J=8.49 Hz, 2 H) 3.91 (s, 3 H) 4.08 (t, J=8.69 Hz, 2 H) 6.67 (s, 1 H) 7.90 (d, J=0.98 Hz, 1 H) 7.96 (dd, J=8.49, 1.46 Hz, 1 H) 8.46 (d, J=8.59 Hz, 1 H) 8.65 (s, 1 H).

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; PFIZER INC.; DAROUT, Etzer; DENINNO, Michael, Paul; FUTATSUGI, Kentaro; GUIMARAES, Cristiano, Ruch, Werneck; LEFKER, Bruce, Allen; MASCITTI, Vincent; MCCLURE, Kim, Francis; MUNCHHOF, Michael, John; ROBINSON, Ralph, Pelton, Jr.; WO2010/128414; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 366452-98-4, 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. 366452-98-4, name is 4-Amino-2,3-dihydro-1H-isoindol-1-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

N-(3-((((2R)-1-Methyl-2-pyrrolidinyl)methyl)oxy)-4-(trifluoromethyl)phenyl)-2-((1-oxo-2,3-dihydro-1H-isoindol-4-yl)amino)-3-pyridinecarboxamide (R) 2-Fluoro-N-[3-(1-methyl-pyrrolidin-2-ylmethoxy)-4-trifluoromethyl-phenyl]-nicotinamide (402 mg, 1.0116 mmol) was dissolved in tert-butanol (1 mL). To this mix was added TFA (115 mg, 1.0116 mmol) and 4-amino-2,3-dihydro-isoindol-1-one (450 mg, 3.035 mmol). The mix was heated for 6 h at 150 C., allowing the solvent to boil off. The reaction was cooled to RT, dissolved into 1N aqueous HCl, basified to pH 10 with solid NaOH, extracted twice with EtOAc, and dried over Na2SO4. The product precipitated out of solution along with a minor by-product. The EtOAc was filtered off. The crude product was dissolved in MeOH and filtered. The MeOH solution was concentrated down and eluted on silica gel column to yield the titled compound as a light yellow solid. MS: C27 H26 F3 N5O3-525.528; M+H 526.1

The synthetic route of 4-Amino-2,3-dihydro-1H-isoindol-1-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Amgen Inc.; US2003/203922; (2003); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, 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 102359-00-2, COA of Formula: C9H7NO3

Into a 25-mL round-bottom flask was placed tert-butyl N-[1-[(1R,3r,5S)-3-amino- 8-azabicyclo[3.2.1]octane-8-sulfonyl]piperidin-4-yl]carbamate (200 mg, 0.51 mmol, 1.00 equiv), dichloromethane (5 mL), 2-oxo-2,3-dihydro-1H-indole-5-carboxylic acid (109 mg, 0.62 mmol, 1.20 equiv), EDCI (118 mg, 0.62 mmol, 1.20 equiv), and HOBT (104 mg, 0.77 mmol, 1.50 equiv). This was followed by the addition of TEA (260 mg, 2.57 mmol, 4.99 equiv) dropwise with stirring at 0oC. The resulting solution was stirred for 14 h at 20oC. The reaction mixture was then diluted with 10 mL of dichloromethane and was washed with 2×5 mL of brine. The organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was chromatographed on a silica gel column with ethyl acetate/petroleum ether (1:1). This resulted in 243 mg (86%) of tert- butyl N-[1-[(1R,3r,5S)-3-(2-oxo-2,3-dihydro-1H-indole-5-carboxamido)-8- azabicyclo[3.2.1]octane-8-sulfonyl]piperidin-4-yl]carbamate as a off-white solid

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Epizyme, Inc.; Poley, Megan Allen Clunan; Kunz, Kevin Wayne; Mills, James Edward John; Mitchell, Lona Helen; munckhof, Michael John; Harvey, Darren Martin; (303 pag.)KR2017/45749; (2017); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem