Author: Jessica.F

These common heterocyclic compound, 7699-18-5, name is 5-Methoxyindolin-2-one, 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. COA of Formula: C9H9NO2

A round bottom flask was charged with 3-(2-(4-methylpiperazin-l-yl)pyrimidin-5- yl)-lH-indazole-6-carbaldehyde (26 mg, 0.80 mmol), 5-methoxyoxindole (13 mg, 0.80 mmol), piperidine (0.8 uL, 0.008 mmol) and MeOH (2 mL). The reaction was then heated to 6O0C for 4 hrs. An orange precipitate formed which was further precipitated by cooling to room temperature. The orange solid was then filtered and washed with MeOH (5 mL) giving 9.8 mg, 26 % of the title compound. 1H NMR (400 MHz, de-DMSO) delta 13.46 (s, IH), 10.44 (s, IH), 8.97 (s, 2H), 8.18 (d, J = 8.5 Hz, IH), 7.94 (s, IH), 7.78 (s, IH), 7.48 (d, J = 8.8 Hz, IH), 7.20 (s, IH), 6.85 (d, J = 10.6 Hz, IH), 6.80 (d, J = 9.0 Hz, IH), 3.82 (br t, 4H), 3.59 (s, 3H), 2.39 (br t, 4H), 2.23 (s, 3H); MS ESI 468.3 [M + H]+, calcd for [C26H25N7O2 + H]+ 468.2.

The synthetic route of 5-Methoxyindolin-2-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY HEALTH NETWORK; WO2009/79767; (2009); A1;,
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Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 324-03-8, name is 6-Fluoroindoline-2,3-dione, 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 324-03-8, Product Details of 324-03-8

6-Fluoro-l-isopropyl-lH-indole-2,3-dione E-1.2′”” To a stirred solution of 6-Fluoro-lH-indole-2,3-dione E-1.2″”” (55.0 g; 333.1 mmol) in DMF (550 ml) is added K2C03 (55.2 g; 399.7 mmol) and 2-Iodo- propane (73.6 g; 433.0 mmol) at 25C. The reaction mixture is stirred at 25C for 16 h. Then the mixture is diluted with water and extracted with ethyl acetate. The organic layer was concentrated under reduced pressure to obtain crude compound. The crude was purified by column chromatography using silicagel (230-400 muMu) with eluting mixture of ethyl acetate and hexane. Yield: 51% (35.0 g; 169.0 mmol) HPLC-MS: (M+H)+ = 208; tRet = 2.02 min; method R D-FA-4.5-MIN

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

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ENGELHARDT, Harald; WO2015/169962; (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. 99365-40-9, name is 6-Bromoindolin-2-one, A new synthetic method of this compound is introduced below., Safety of 6-Bromoindolin-2-one

Preparation 1: 6-Iodooxindole A schlenk tube and stir bar were dried in an oven overnight and then were evacuated, filled with Ar(g) and cooled. The schlenk tube was charged with CuI (45 mg, 0.236 mmol, 5 mol %), 6-bromoxindole (1.0 g, 4.72 mmol), and NaI (1.42 g, 9.44 mmol). The schlenk tube was evacuated and backfilled with Ar(g) (3 times). Racemic trans-N,N’-dimethyl-1,2-cyclohexanediamine (74 muL, 0.472 mmol, 10 mol %) and anhydrous dioxane (4.72 mL) were added via syringe under Ar(g). The schlenk tube was sealed with a teflon valve and the suspension was stirred at 110 C. for 24 h. The reaction was then cooled to room temperature and 15% NH4OH(aq) (50 mL) was added to the reaction mixture while stirring. The suspension was allowed to stir for about 30 min after which the tan solid was vacuum filtered and dried affording 6-Iodooxindole in 84% yield (1.027 g, 3.96 mmol).

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

Reference:
Patent; Allergan, Inc.; US2007/15748; (2007); A1;,
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Indoline | C8H9N – PubChem

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 64483-69-8 as follows. Recommanded Product: 64483-69-8

5-Acetyl-2-oxindole (2 g) in 15 mL trifluoroacetic acid in an ice bath was slowly treated with 1.8 g triethylsilane and then stirred at room temperature for 5 hours. One mL of riethylsilane was added and the stirring continued overnight. The reaction mixture was poured into ice water and the resulting precipitate collected by vacuum filtration, washed copiously with water and dried under vacuum to give 1.3 g (71% yield) of the title compound as a yellow solid. 1H-NMR (360 MHz, DMSO-d6): delta 10.25 (s, br, NH-1), 7.03 (s, 1 H, H-4), 6.97 (d, J=8.05 Hz, 1 H, H-6), 6.69 (d, J=8.05 Hz, 1 H, H-7), 3.40 (s, 2 H, CH2-3), 2.51 (q, J=7.69 Hz, 2 H, CH2CH3-5), and 1.12 (t, J=7.42 Hz, 3 H, CH2CH3-5).

According to the analysis of related databases, 64483-69-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sugen, Inc.; US6395734; (2002); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 7147-90-2,Some common heterocyclic compound, 7147-90-2, name is 5-Chloroisoindoline-1,3-dione, molecular formula is C8H4ClNO2, 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: Phthalimide 6a (148mg, 1mmol), 124 1,4-dibromobutane (1.080g, 5mmol), 12 potassium carbonate (276mg, 2mmol) was added to 115 acetone (3mL), and the reaction mixture was refluxed for 2h. After cooling to room temperature, the reaction mixture was purified by column chromatography using 125 PE: acetone (40:1) as eluent to give 126 7a (260mg, 92%) as a white solid.

The synthetic route of 7147-90-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Xu, Mingshuo; Wang, Yu; Yang, Feipu; Wu, Chunhui; Wang, Zhen; Ye, Bin; Jiang, Xiangrui; Zhao, Qingjie; Li, Jianfeng; Liu, Yongjian; Zhang, Junchi; Tian, Guanghui; He, Yang; Shen, Jingshan; Jiang, Hualiang; European Journal of Medicinal Chemistry; vol. 145; (2018); p. 74 – 85;,
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Indoline | C8H9N – PubChem

Electric Literature of 4702-13-0, 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. 4702-13-0 name is N-Phthaloylglycine, 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:; To a stirred solution of A/-phthaloylglycine (11.92 g, 58 mmol) indichloromethane (200 mL) at room temperature, oxalyl chloride (7.5 mL, 87mmol) was added. DMF (two drops) was then added. The resulting solutionwas concentrated after stirring four hours at room temperature.Dichloromethane (100 mL, dry) was then added to the residue. Benzylamine(9.5 mL, 87 mmol) was added slowly into the resulting solution. Triethylamine(12 mL, 87 mmol) was then added slowly into the solution. Dichloromethane(200 mL) and methanol (50 mL) were added 30 min after the completedaddition of triethylamine. The resulting solution was extracted with 2 N HCIsolution twice, 1 N NaOH solution one time and 1 N HCI one time, and thendried over MgSO4. The solution was filtered and concentrated to yield N-benzyl-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-acetamide as a white solid.MH+= 294.9.

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

Reference:
Patent; JANSSEN PHARMACEUTICA, N.V.; BAXTER, Ellen; BOYD, Robert; COATS, Steve; JORDAN, Alfonzo; REITZ, Allen; REYNOLDS, Charles H.; SCOTT, MALCOLM; SCHULZ, Mark; DE WINTER, Hans Louis Jos; WO2006/17844; (2006); A1;,
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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. 181140-34-1, name is (R)-(-)-N-(2,3-Epoxypropyl)phthalimide, A new synthetic method of this compound is introduced below., category: indolines-derivatives

General procedure: Compounds 3-7 have been synthesized using a procedure originally reported by Roehrig et al.16 Chiral amine or amino alcohol (0.6 mmol, 1.2 equiv) in 10 mL isopropanol was added to the solutionof (R)-N-(2,3-epoxypropyl)phthalimide (102 mg, 0.50 mmol)in 10 mL of isopropanol at in an ice bath and stirred for 1 h. then refluxed for 12 h. The reaction monitored by TLC. Solvent was removed by rotary evaporator under reduced pressure after completion of the reaction.

The synthetic route of 181140-34-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Karakaplan, Mehmet; Jameel, Basam; Tetrahedron Asymmetry; vol. 27; 14-15; (2016); p. 597 – 602;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

201940-08-1, name is tert-Butyl 5-bromoisoindoline-2-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. category: indolines-derivatives

To solution of the aryl bromide (0.200 g, 0.67 mmol) and Pd (PPh3) 4 (39 mg, 0.33 mmol) dissolved in THF under N2 was cannulated the crude vinyl zinc species from step A. The reaction was heated at 50C for 36 hours, and the then filtered through a plug of A1203 with aid of EtOAc and concentrated to give an oil which was used without further purification

The synthetic route of 201940-08-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; INTERMUNE, INC.; ARRAY BIOPHARMA INC.; WO2005/37214; (2005); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 20870-79-5, 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. 20870-79-5, name is 5-Nitroindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

5-Amino-2-oxindole 5-Nitro-2-oxindole (6.3 g) was hydrogenated in methanol over 10% palladium on carbon to give 3.0 g (60% yield) of the title compound as a white solid,

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

Reference:
Patent; Sugen, Inc.; US6878733; (2005); B1;,
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. 16800-68-3, name is 1-Acetylindolin-3-one, This compound has unique chemical properties. The synthetic route is as follows., Safety of 1-Acetylindolin-3-one

3 – (3 – 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, 45 mg and gave rise 96% to unit_.

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 16800-68-3.

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