Category: indolines-derivatives

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. 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-one, A new synthetic method of this compound is introduced below., HPLC of Formula: C10H9Cl2NO

EXAMPLE 3; 5-(2-(4-Benzo[d]isothiazol-3-yl)piperazin-1-yl)ethyl)-6-chloro-1,3-dihydro-2H-indol-2-one hydrochloride. (I); A reactor is loaded with 131 g (0.57 mol) of 6-chloro-5-(2-chloro-ethyl)-1,3-dihydro-indol-2-one, 125 g (0.57 mol) of piperazinyl benzoisothiazole, 260 ml of dimethylsulfoxide, 26 ml of water and 4.3 g (0.0285 mols) of Nal. The reaction mixture is added with 103 g (0.969 mol) of Na2CO3, with stirring under nitrogen atmosphere. The resulting mixture is heated to about 115-125 C. in 1 h and kept at said temperature under stirring for approx. 1 hr 45 min, then cooled and slowly added in about 25 min with isopropyl alcohol (650 ml), at a temperature of about 110 C., then slowly cooled at 25 C. The filtrate and the precipitate are washed with isopropyl alcohol (2×130 ml) to obtain 310 g of 5-(2-(4-benzo[d]isothiazol-3-yl) piperazin- 1-yl)ethyl)-6-chloro- 1,3-dihydro-2H-indol-2-one free base, as a crystalline solid. The resulting product is placed in a 3 L beaker with 1500 ml of purified water, and 150 ml of 32% HCl are dropped therein with stirring. The reaction mixture is kept under stirring for 10 min, filtered, washed with purified water (2×500), dried to give 260 g of 5-(2-(4-benzo[d]isothiazol-3-yl) piperazin- 1-yl)ethyl)-6-chloro- 1,3-dihydro-2H-indol-2-one hydrochloride, as a crystalline solid.

The synthetic route of 118289-55-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DIPHARMA S. P. A.; LUNDBECK PHARMACEUTICALS ITALY S. P. A.; US2007/117810; (2007); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 7147-90-2, name is 5-Chloroisoindoline-1,3-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. HPLC of Formula: C8H4ClNO2

Nitrogen protected, cooled to -15 C, 0.60 g (2.5 mmol) of 3-n-butyl-5-chloro-3-hydroxyisoindolin-1-one and 3-n-butyl-6-chloro-3 -A mixture of hydroxyisoindolin-1-one was dissolved in 30 ml of DCM, and then 2.9 g (25.0 mmol) of triethylsilane and 1.1 g (7.5 mmol) of boron trifluoride ether solution were added, and the temperature was returned to room temperature, and the reaction was performed. Overnight, TLC showed the reaction was complete.The reaction solution was poured into a 5% sodium solution, extracted with DCM, dried, concentrated, and subjected to silica gel column chromatography. A mixed eluent of ethyl acetate and petroleum ether was used as the eluent (the volume ratio of ethyl acetate and petroleum ether was 1: 1), get:3-n-butyl-5-chloroisoindolin-1-one (A) (small polar point, first eluted component), yield 35.7%.3-n-butyl-6-chloroisoindolin-1-one (B) (a point of great polarity, the second elution component), with a yield of 37.5%.

The synthetic route of 5-Chloroisoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Aisite (Chengdu) Bio-pharmaceutical Co., Ltd.; Fu Jiasheng; Chen Xing; Yang Youzhe; Chen Xiaogang; Chen Jiachang; Sun Jingxiong; Gan Man; Guo Peng; (41 pag.)CN110563631; (2019); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 552330-86-6, name is 5-Bromoisoindolin-1-one, 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 552330-86-6, category: indolines-derivatives

5-Bromo-2,3-dihydro-isoindol-l-one (230mg, 1.08mmol), bis(pinacolato)diboron(300mg, l.ldeltammol), PdCl2dppf (25mg, 31mumol) and KOAc (320mg, 3.26mmol) are suspended in dioxane (4mL), purged with nitrogen for 5 minutes and then heated at 850C overnight. The solvent is removed in vacuo and the residue partitioned between ethyl acetate and water. The aqueous layer is extracted with ethyl acetate (3x) and the combined organic phases are washed once with brine, filtered through MgStheta4 and evaporated. The solid residue is triturated with hexane and dried in vacuo to yield the title compound (185mg, 66 %) as a grey solid. 1H-NMR (400MHz, CDCl3) delta(ppm) 1.37 (12H, s), 4.45 (2H, s), 6.38 (IH, br s), 7.87 (IH, d), 7.93 (2H, m).

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; GALAPAGOS N.V.; WO2007/138072; (2007); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 1914-02-9, 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. 1914-02-9, name is 3,3-Dimethylindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of (S)-2-((tert-butoxycarbonyl)amino)propanoic acid (133 mg, 0.703 mmol) in 7 mL DMF, triethylamine (127 mu^ 0.912 mmol) and HATU (319 mg, 0.839 mmol) were added. After stirring at room temperature for 5 min, 3,3-dimethylindoline (97.2 mg, 0.660 mmol) was added. After stirring at room temperature for 4 h, the mixture was extracted with AcOEt and brine. The organic phase was dried over MgS04, filtered, and concentrated. The residue was purified by silica gel column chromatography to give (S)-tert-butyl (l-(3,3-dimethylindolin-l-yl)-l-oxopropan-2-yl)carbamate (204 mg) as a white solid. LCMS m/z = 319.4 [M+l]+; NMR (400 MHz, CDC13) delta ppm 1.358 (s, 3H), 1.364 (s, 3H), 1.40 (d, J = 6.8 Hz, 3H), 1.45 (s, 9H), 3.78 (d, J = 10.0 Hz, 1H), 4.00 (d, J = 10.0 Hz, 1H), 4.54-4.61 (m, 1H), 5.46 (d, J = 8.5 Hz, 1H), 7.07-7.10 (m, 1H), 7.15-7.16 (m, 1H), 7.20-7.24 (m, 1H), 8.17 (d, J = 8.1 Hz, 1H).

The synthetic route of 3,3-Dimethylindoline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; SEMPLE, Graeme; BEHAN, Dominic P.; FEICHTINGER, Konrad; GLICKLICH, Alan; GROTTICK, Andrew J.; KAM, Maria Matilde Sanchez; KASEM, Michelle; LEHMANN, Juerg; REN, Albert S.; SCHRADER, Thomas O.; SHANAHAN, William R.; WONG, Amy Siu-Ting; ZHU, Xiuwen; WO2015/66344; (2015); A1;,
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. 6780-38-7, name is 2-(1,3-Dioxoisoindolin-2-yl)acetyl chloride, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C10H6ClNO3

84.1To a solution of 2-amino-nicotinamide [13438-65-8](3.0 g, 21.9 mmol) in CH2Cl2 (120 ml) and pyridine (10.56 ml, 131.3 mmol) was added phthalyl-glycyl-chloride (5.87 g, 26.3 mmol) at 0 C. The solution turned to a white suspension while stirring 0.5 hours at 0 C. and 1 hour at ambient temperature. The solid was filtrated and washed with CH2Cl2 to obtain 2-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-acetylamino]-nicotinamide (7.10 g, 21.9 mmol; 100%) as white solid. MS (m/e): 325.1 [M+H+].

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 6780-38-7.

Reference:
Patent; Conte, Aurelia; Dehmlow, Henrietta; Grether, Uwe; Kratochwil, Nicole A.; Kuehne, Holger; Narquizian, Robert; Panousis, Constantinos; Peters, Jens-Uwe; Ricklin, Fabienne; Roever, Stephan; US2007/275987; (2007); A1;,
Indoline – Wikipedia,
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 340702-10-5 as follows. Computed Properties of C8H6FNO

[0128] Step c: To a 0 C suspension of 6-fluoroisoindoline-l-one (8.0 g, 5.3 mmol) in concentrated H2S04was added drop-wise a pre-cooled mixture of concentrated H2S04(26 mL) and nitric acid (6 mL) while keeping the reaction mixture below 5 C. After addition, the reaction mixture was slowly warmed to room temperature during overnight. Ice (50 g) was added to the mixture and the solid was collected and dried, then washed with MTBE (50 mL) and ethyl acetate (50 mL) to give the desired product as a light yellow solid (5.1 g, 50%). MS: (ES) m/z calculated for C8H6FN203[M + H]+197, found 197.

According to the analysis of related databases, 340702-10-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CHEMOCENTRYX, INC.; CHEN, Xi; DRAGOLI, Dean, R.; FAN, Junfa; KALISIAK, Jaroslaw; LELETI, Manmohan, Reddy; MALATHONG, Viengkham; MCMAHON, Jeffrey; TANKAKA, Hiroko; YANG, Ju; YU, Chao; ZHANG, Penglie; MALI, Venkat; (104 pag.)WO2017/87610; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-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 5332-26-3, Recommanded Product: 5332-26-3

General procedure: The benzofused N-heteroaromatic alkynes 2, 5, and 8 weresynthesized by reacting benzimidazole (1.0 mmol),benzotriazole (1.0 mmol), or carbazole (1.0 mmol) withpropargyl bromide (1.2 mmol) in the presence of potassiumcarbonate (2.0 mmol) using dimethylformamide bycontinuous stirring at 10-25 C up to 8-10 h [32]. For thesynthesis of target compounds, solution of aromatic bromides(1.0 mmol) in dimethylformamide was taken in around-bottomed flask and aqueous solution of sodium azide(3.0 mmol) was added, thereafter, stirred the reactionmixture for 1 h at 25-40 C. To the above reaction mixture,benzofused N-heteroaromatic alkyne 2 (1.0 mmol), 5(1.0 mmol), or 8 (1.0 mmol) was added followed by coppersulfate pentahydrate (5 mol %) and sodium ascorbate(10 mol %) [33], then, stirred the reaction contents overnight.The progress of reaction was monitored by thin layerchromatography. After the completion of reaction, ice-colddistilled water was added to the reaction mixture andproduct was extracted with ethyl acetate (50 cm3 9 3).The organic layer was washed with aqueous ammoniasolution followed by brine solution and dried using anhydroussodium sulfate. Filtered and evaporated the solventunder vacuum to get crude product which was furtherpurified by column chromatography using hexane:ethylacetate (7:3) as eluent.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(Bromomethyl)isoindoline-1,3-dione, and friends who are interested can also refer to it.

Reference:
Article; Kaushik; Kumar, Krishan; Lal, Kashmiri; Narasimhan, Balasubramanian; Kumar, Ashwani; Monatshefte fur Chemie; vol. 147; 4; (2016); p. 817 – 828;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 89-40-7, name is 5-Nitroisoindoline-1,3-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 89-40-7, SDS of cas: 89-40-7

Add 112.8 g of stannous chloride dihydrate and 70 mL of concentrated hydrochloric acid to a 500 mL three-necked flask, and stir until completely dissolved.19.2 g of 4-nitrophthalimide was added, and the reaction was stopped after reacting at 40 C for 1 h.The reaction solution was suction filtered to obtain a filter residue, and the filter residue was washed twice with 50 mL of concentrated hydrochloric acid and then dried.After washing twice with 50 mL of ethyl acetate, a second suction filtration was performed.The filter residue obtained by the second suction filtration was dried to obtain 14.9 g of 4-aminophthalimide yellow powder, and the yield was 92%.

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-Nitroisoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; WUYI UNIV; Wuyi University; ZHAO JUAN; Zhao Juan; (7 pag.)CN107778211; (2018); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 56341-37-8, These common heterocyclic compound, 56341-37-8, name is 6-Chlorooxindole, 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.

NBS (5.8 g, 32.8 mmol) was added to a solution of 6-chlorooxiindole (5.0 g, 29.8 mmol) in acetonitrile (50 mL) at -10 00 . The reaction mixture was stirred at room temperature for 3 h. The reaction was monitored by LC-MS. The reaction mixture was evaporated to dryness and was extracted with ethyl acetate. The ethyl acetatelayer was washed with water and dried over anhydrous Na2SO4 and concentrated under reduced, which was purified by trituration with n-hexane to yield title compound (7.0 g, 95.8 %) as a brown solid. LOMS: (M-H) = 244.9; 1H NMR: (DMSO-d6, 300MHz) 6 10.61(s, 1H), 7.56(s, 1H), 6.98(s, 1H), 3.51(s, 2H).

The synthetic route of 56341-37-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; MADANAHALLI RANGANATH RAO, Jagannath; GURRAM RANGA, Madhavan; PACHIYAPPAN, Shanmugam; WO2014/202580; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 446292-08-6, 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. 446292-08-6, name is (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Methylamine (35% in ethanol, 5kg) was added to a suspension of compound according to e.) (4.79kg) in ethanol (36kg) . The reaction mixture was heated to 65 0C for 4 hours. After cooling to 58-60 0C, a total of 7L of 5M hydrochloric acid solution is added until the pH is 2.7, after which the product starts to crystallize. After cooling to 20 0C, the precipitated reaction product is filtered off with suction, washed with CH2Cl2 (8L*2) and then dried to obtain 3.11kg of the product (Yield 83.7%)

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, (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; KRKA, D.D., NOVO MESTO; ZUPANCIC, Silvo; PECAVAR, Anica; WO2011/12321; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem