Indolines-derivatives

Synthetic Route of 16800-68-3, 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. 16800-68-3, name is 1-Acetylindolin-3-one, This compound has unique chemical properties. The synthetic route is as follows.

3 – (2 – Methylphenyl) propyne acid 4 – nitrophenyl-unitz (84.3 mg 0.3 mmol), was obtained. N- Acetylindole -3 -unitz 26.3 mg (0.15 mmol), the carbene-unitz (0.015 mmol), 3.96 mg, 1 diazabicycloundecene 8 – (-7 -) and methylene-methylene chloride shown in Formula 45 mul IV 0.3 mmol were placed in 3 ml a 25 ml unitunito-two-port 2h bottle, and reacted 30 C, under unituniteous conditions, and concentrated, under inert atmosphere protection, unitant-like conditions. The eluate fractions of all the products 10:1 detected were collected by chromatography with petroleum ether: ethyl acetate in the timetime as eluent column chromatography, and the solvent was evaporated to obtain the residue unit, 43 mg and gave rise 91% to unit_.

The chemical industry reduces the impact on the environment during synthesis 1-Acetylindolin-3-one. I believe this compound will play a more active role in future production and life.

Reference:
Patent; China Pharmaceutical University; Du Ding; Sun Kewen; (10 pag.)CN110156800; (2019); A;,
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Indoline | C8H9N – PubChem

Related Products of 1504-06-9, A common heterocyclic compound, 1504-06-9, name is 3-Methyloxindole, molecular formula is C9H9NO, 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.

The amount of surfactant SDS is increased,30 mol% (ie 28.8 mg) of 3-methyl-2-indanone,The remaining conditions are the same as in Embodiment 1,The yield of the target product 3-methyl-3-hydroxy-2-indanone was 84%.

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; Ningbo University; Bao Wenhui; Wei Wenting; Gao Lehan; Wang Xinye; (12 pag.)CN108409630; (2018); A;,
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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. 64483-69-8, name is 5-Acetylindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Product Details of 64483-69-8

A mixture of 5-acetyl-2-oxindole (70 mg), 3-methylindole-2-carbaldehyde (56 mg) (prepared according to Synthetic Communications, 1986, 16, 1799) and piperidine (30 mg) in ethanol (1 mL) was heated in a sealed tube at 90 C. for overnight. The mixture was cooled to room temperature. The solid was collected by vacuum filtration, washed with cold ethanol and dried in oven for overnight to give 83 mg (75% yield) of 5-acetyl-3-(3-methyl-1H-indol-2-ylmethylene)-1,3-dihydro-indol-2-one. 1H NMR (360 MHz, DMSO-d6) 12.86 (s, br, 1H, NH), 11.29 (s, br, 1H, NH), 8.43 (d, J=1.5 Hz, 1H, H-4), 8.01 (s, 1H, vinyl), 7.78 (dd, J=1.5 and 8 Hz, 1H, H-6), 7.58 (d, J=8 Hz, 1H), 7.45 (d, J=8 Hz, 1H), 7.23 (t, 1H), 7.01 (t, 1H), 6.92 (d, J=8 Hz, 1H), 2.58 (s, 3H, CH3), 2.54 (s, 3H, CH3). MS m/z 317.2 [M+1]+.

The synthetic route of 64483-69-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUGEN, Inc.; US2002/183364; (2002); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 21857-45-4, name is 5-Methoxyindoline, molecular formula is C9H11NO, 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. HPLC of Formula: C9H11NO

Example 44 6,7-Dimethoxy-4-(5-methoxy-2,3-dihydro-indol-1-yl)-quinazoline methanesulfonate salt Utilizing a procedure analogous to that described in Example 1, this product was prepared in 95% yield from 5-methoxy-indoline (1.1 eq.), and 4-chloro-6,7-dimethoxy-quinazoline (1.0 eq) in i-PrOH. The free-base obtained following column chromatography on silica (45% acetone/hexanes) was dissolved in minimal CH2 Cl2 and treated with 1 eq. of methanesulfonic acid in CH2 Cl2 followed by dilution with several volumes of ether to precipitate the mesylate salt which was filtered and added in vacuo. (M.P. 285-292 C. (dec); LC-MS: 338 (MH+); anal. RP18-HPLC RT: 3.82 min.).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 21857-45-4, its application will become more common.

Reference:
Patent; Pfizer Inc.; US5736534; (1998); A;,
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

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

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

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. 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

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