Author: Jessica.F

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

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

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

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

Synthetic Route of 18711-13-2, A common heterocyclic compound, 18711-13-2, name is 4,7-Dichloroindoline-2,3-dione, molecular formula is C8H3Cl2NO2, 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 II-96 : (2-Oxo-1, 2-dihydro-pyrimidin-5-yl)-acetic acid [(3Z)-4,7-dichloro-2-oxo-1,2- DIHYDRO-INDOL-3-YLIDENE]-HYDRAZIDE [0639] The (at)TURE OF (2-OXO-1,2-DIHYDRO-PYRIMIDIN-5-YL)-ACETIC ACID HYDRAZIDE (67 MG, 0. 4 mmol) and 4,7-dichloro-isatin (95 mg, 0.44 mmol) in AcOH (10 mL) was stirred at 100″C FOR 3 h. After removal of the solvent, the residue was CRYSTALLIZED FROM MEOH TO GIVE THE TITLE compound as yellow solid (45 mg, 31%). [0640] H-NMR (400 MHz, DMSO-d6) 612. 68 (s, 1H), 11.92 (s, 1H), 8.41 (s, 2H), 7.46 (d, 1H), 7.16 (d, 1H), 4.00 (s, 2 H); MS (m/z) 366 [M+1].

The synthetic route of 18711-13-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUGEN, INC.; WO2005/5378; (2005); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 7223-50-9, A common heterocyclic compound, 7223-50-9, name is N-Propargylphthalimide, molecular formula is C11H7NO2, 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.

General procedure: A mixture of a terminal alkyne (2.0 mmol), paraformaldehyde (180.2 mg, 2.0 mmol), amine (2 mmol) and Pt/TiO2 (5.0 mg, 0.25 mol%) loaded in distilled H2O (3 mL) and heated under microwave condition at 140 C and 250 W for appropriate reaction time (the reaction was monitored by TLC). After the completion of the reaction, the mixture was allowed to cool down and then extracted with EtOAc (3*20 mL). The combined organic extracts were dried (MgSO4) and fltered. The solvent was evaporated under reduced pressure and the resulting crude product was purifed by column chromatography (silica gel) to obtain the corresponding products 4a-4l.

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; Mohamed, Yasser M. A.; El Nazer, Hossam A.; Solum, Eirik Johansson; Chemical Papers; vol. 73; 2; (2019); p. 435 – 445;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 5332-26-3,Some common heterocyclic compound, 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, molecular formula is C9H6BrNO2, 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: 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.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(Bromomethyl)isoindoline-1,3-dione, its application will become more common.

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

Application of 480-91-1, 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. 480-91-1 name is Isoindolin-1-one, 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.

At 0 C., 611.3 mg (15.3 mmol, 60% pure) of sodium hydride were added to 2.035 g (15.3 mmol) of 1-oxoindoline in 12 ml of DMF. The mixture was stirred for 30 min, and 6.0 g (12.7 mmol) of tert-butyl(+/-)-[4-(bromomethyl)phenyl](cyclopentyl)acetate were then added at 0 C. The reaction mixture was stirred for a further 4 h, water was then added and the mixture was extracted twice with dichloromethane. The combined organic phases were washed with saturated sodium chloride solution, dried over magnesium sulfate and concentrated. The crude product was treated with diethyl ether in an ultrasonic bath and the solid was isolated by filtration. This gave 3.40 g (60.2% of theory) of the target compound.LC-MS (method 11): Rt=1.57 min; m/z=350 (M-C4H8+H)+.1H-NMR (400 MHz, DMSO-d6): delta=7.72 (d, 1H), 7.60-7.50 (m, 3H), 7.30 (d, 2H), 7.21 (d, 2H), 4.71 (s, 2H), 4.38 (s, 2H), 3.18 (d, 1H), 2.35 (m, 1H), 1.85-1.37 (m, 5H), 1.34 (s, 9H), 1.20 (m, 2H), 0.91 (m, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Isoindolin-1-one, and friends who are interested can also refer to it.

Reference:
Patent; BAYER SCHERING PHARMA AKTIEGESELLSCHAFT; US2011/34450; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 169037-23-4, A common heterocyclic compound, 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, molecular formula is C9H4F3NO3, 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.

General procedure: To a solution of isatin 1 (1 mmol) in toluene (5 mL) was added the solution of trialkyl/aryl Al 2 (2 mmol, 2 M in toluene) dropwise at RT. Then the mixture was heated at 70 C and stirred for additional 3-3.5 h (see Table 2). The reaction was monitored by TLC. After completion of the reaction, toluene was evaporated and extracted with ethyl acetate (3 × 5 mL). The combined organic layer was washed with brine solution, dried over anhydrous Na2SO4, and concentrated under reduced pressure (rotary evaporator). The crude products were purified by silica gel column chromatography using ethyl acetate/hexanes (4:1-1:1). All compounds were characterized by (MP, NMR, Mass, and IR) spectral data.18

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; Kumar, G. Santosh; Ramesh, Palakuri; Kumar, A. Sanjeeva; Swetha; Meshram; Tetrahedron Letters; vol. 54; 37; (2013); p. 5048 – 5051;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 114041-16-6,Some common heterocyclic compound, 114041-16-6, name is 5,6-Dimethoxyisoindoline, molecular formula is C10H13NO2, 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.

Compound 250:2-chloropyrimidine derivative 249 (50 mg) and isoindoline (50 mg) were dissolved in Acetonitrile (5 mL) and the mixture was heated to 80 C and stirred for 1 hour. The solvent was removed by concentration and the residue was purified by Prep-LC gave compound 250. HPLC-MS tR = 1.63 min (UV254 nm); mass calculated for formula 029H35N7O5 561.3, observed LCMS m/z 562.3 (M+H).

The synthetic route of 114041-16-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; WO2009/14637; (2009); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem