Tag: M.W=200-300

These common heterocyclic compound, 675109-26-9, name is 6-Bromoisoindolin-1-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. HPLC of Formula: C8H6BrNO

TDI01239-1 (500 mg, 2.358 mmol) was dissolved in tetrahydrofuran (24 mL), and cooled to 0 C. Under theprotection of nitrogen, 60% NaH (236 mg, 5.895 mmol) was added to the above reaction solution, and the reaction wasperformed at room temperature for 1h after the addition. Bromoethyl acetate was then added at 0 C, and the reactionwas continued at room temperature for 2h. LC-MS indicated the reaction was complete. After completion of the reaction,ice water and IN HCl solution was added to quench the reaction, and the aqueous phase was extracted with ethyl acetate(15 mL). The combined organic phase was washed with saturated brine, dried over anhydrous sodium sulfate andconcentrated to dryness to afford TDI01239-2 (700 mg, yellow solid, yield: 99.57%). MS m/z (ESI): 298.1 [M+H].

The synthetic route of 6-Bromoisoindolin-1-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Beijing Tide Pharmaceutical Co., Ltd.; Zhao, Yanping; Wang, Hongjun; Li, Gong; Jiang, Yuanyuan; Li, Xiang; Zhou, Liying; Liu, Yanan; (235 pag.)EP3421465; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 118289-55-7, A common heterocyclic compound, 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-one, molecular formula is C10H9Cl2NO, 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 1 Synthesis of Ziprasidone To a 125 mL round bottom flask equipped with an N2 inlet and condenser are added 0.73 g (3.2 mmol) 5-(2-chloroethyl)-6-chloro-oxindole, 0.70 g (3.2 mmol) N-(1,2-benzisothiazol-3-yl)piperazine, 0.68 g (6.4 mmol) sodium carbonate, 2 mg sodium iodide, and 30 mL methylisobutyl ketone. The reaction is refluxed for 40 hours, cooled, filtered, and evaporated. The residue is chromatographed on silica gel, eluding the by-products with ethyl acetate (1 L) and the product with 4% methanol in ethyl acetate (1.5 L). The product fractions (Rf=0.2 in 5% methanol in ethyl acetate) are evaporated, taken up in methylene chloride, and precipitated by addition of ether saturated with HCl; the solid is filtered and washed with ether, dried, and washed with acetone. The latter is done by slurrying the solid with acetone and filtering.

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

Reference:
Patent; Barberich, Timothy J.; Rubin, Paul D.; Yelle, William E.; US2006/19970; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 1035235-27-8, name is tert-Butyl 4-bromoisoindoline-2-carboxylate belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Product Details of 1035235-27-8

tert-Butyl 4-bromoisoindoline-2-carboxylate (163 mg, 0.548 mmol), methyl 3-hydroxybenzoate (100 mg, 0.657 mmol), di-tert-butyl(2?,4?,6?-triisopropyl-[1,1?-biphenylj-2-yl)phosphine (23 mg, 0.055 mmol), palladium(II) acetate (12 mg, 0.055 mmol) and potassium phosphate (233 mg, 1.10 mmol) were added to a vial, which was then evacuated and back-filled with argon three times. Degassed toluene (1.8 mL) was added. The reaction mixture was stirred at 115 C for 16 h. The reaction mixture wasdiluted with DCM, filtered, and purified by flash chromatography to give 231A (55 mg,27%) as a colorless oil. MS(ESI) m/z 269.9 (M-Boc+H).

The synthetic route of 1035235-27-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; SMALLHEER, Joanne, M.; SHAW, Scott, A.; HALPERN, Oz, Scott; HU, Carol, Hui; KICK, Ellen, K.; (311 pag.)WO2017/40449; (2017); 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. 20780-72-7, name is 4-Bromoisatin, A new synthetic method of this compound is introduced below., Product Details of 20780-72-7

General Procedure 3 Suzuki Coupling of 4-bromoindoline-2,3-dione Derivatives with Trifluoroborate Potassium Salts [0344] 4-Bromoisatin (1 eq) was added to a solution of the potassium trifluoroborate salt (1.4 eq), K3PO4 (3.6 eq) and degassed solvent. The reaction mixture was degassed and Pd(PPh3)2Cl2 or Pd(dppf)2Cl2 (0.1 eq) was added. The reaction vessel was sealed and heated by microwave irradiation (Biotage Initiator) for 4 h at 130° C. The reaction mixture was cooled to rt, diluted with EtOAc (10 mL/mmol substrate) and filtered through Celite®. The organic solution was washed with brine (10 mL/mmol substrate) and the resulting aqueous layer was further extracted with EtOAc (2×). The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo to give the crude product which was purified as specified below. Example 51-preparation of 2?-(((9-Cyclopropyl-5H-[1,2,4]triazino[5,6-b]indol-3-yl)thio)methyl)benzonitrile 4-Cyclopropylindoline-2,3-dione Following General Procedure 3,4-bromoisatin (300 mg, 1.33 mmol), potassium cyclopropyltrifluoroborate (275 mg, 1.86 mmol), K3PO4 (1.01 g, 14.8 mmol) and Pd(dppf)2Cl2 (93 mg, 0.13 mmol) in THF/ H2O (3:1, 4 mL) gave the crude reaction mixture, which was purified via flash column chromatography (eluent 30-40° C. petrol/acetone, 4:1) to afford the product as an orange solid. (36 mg, 43percent). [0645] deltaH (500 MHz, DMSO-d6); 0.80-0.84 (2H, m), 1.06-1.15 (2H, m), 2.78-2.89 (1H, m), 6.49 (1H, d, J=7.8 Hz), 6.62 (1H, d, J=7.8 Hz), 7.40 (1H, app t, J=7.8 Hz), 10.98 (1H, br s) [0646] deltaC (125 MHz, DMSO-d6) 10.6, 10.9, 108.4, 116.8, 126.3, 138.2, 147.6, 150.4, 159.2, 176.7 [0647] mp 145-148° C.

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; Christou, Ivy; Cross, Rebecca Lillian; Gianella-Borradori, Matteo; Greaves, David Robert; Russell, Angela Jane; Wynne, Graham Michael; US2014/378451; (2014); 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. 5394-18-3, name is 2-(4-Bromobutyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Formula: C12H12BrNO2

General procedure: For the synthesis of compounds 6a-d we used commercially available (from Sigma Aldrich) N-(bromoalkyl)isoindoline-1,3-diones. To the solution of N-(bromoethyl)isoindoline-1,3-dione (3.93 mmol) in DMF, sodium azide (11.79 mmol) was added and the contents were heated at 80 C for 6-8 h. After completion, reaction mixture was quenched with ice water and extracted with DCM thrice. The organic extracts were combined, dried over anhydrous sodium suphate, filtered, and concentrated under reduced pressure to give corresponding products as colorless oil and was used without further purification

The synthetic route of 5394-18-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kushwaha, Khushbu; Kaushik, Nagendra; Lata; Jain, Subhash C.; Bioorganic and Medicinal Chemistry Letters; vol. 24; 7; (2014); p. 1795 – 1801;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 99365-40-9, name is 6-Bromoindolin-2-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 99365-40-9, Formula: C8H6BrNO

a) 6′-Bromospirorcyclopropane-l,3′-indolinl-2′-one A solution of 6-bromoindolin-2-one (2 g, 9.43 mmol) and diisopropylamine (2.00 g, 2.82 ml, 19.8 mmol) in tetrahydrofuran (16 ml) was cooled to -25C and a solution of nBuLi (1.6 M in hexane, 23.6 ml, 37.7 mmol) was added dropwise. The reaction mixture was warmed to 0C and a solution of 1,2-dibromoethane (5.32 g, 2.44 ml, 28.3 mmol) in tetrahydrofuran (2 ml) was added dropwise. The reaction mixture was warmed to room temperature, stirred for 20 hours and carefully quenched with brine (2 ml) and cone. HC1 (2 ml, ice bath). The reaction mixture was diluted with tert-butyl methyl ether and water. The aqueous phase was extracted with tert-butyl methyl ether, the combined organic phases were washed with brine and dried over sodium sulfate. The solvent was evaporated and the residue purified by silica gel chromatography using ethyl acetate/ heptane as eluent. The title compound was obtained as red crystals (1.11 g). MS ESI (m/z): 238.3/ 240.3 [(M+H)+]. 1H NMR (DMSO-D6, 400 MHz): (ppm) = 10.67 (bs, IH), 7.12-7.09 (m, IH), 7.03 (m, IH), 6.95-6.92 (m, IH), 1.61-1.57 (m, 2H), 1.49-1.45 (m, 2H).

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

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BRUNNER, Daniela; MALBERG, Jessica; SHANKAR, Bavani G.; KOLCZEWSKI, Sabine; LIMBERG, Anja; PRINSSEN, Eric; RIEMER, Claus; STOLL, Theodor; WO2014/40969; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 169037-23-4, These common heterocyclic compound, 169037-23-4, name is 5-(Trifluoromethoxy)indoline-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.

Weigh out 0.35 g (0.0015 mol) of 5-trifluoromethoxy ruthenium,0.39 g (0.0016 mol) of 5-bromoanthoic anhydride was added to a 100 ml three-necked flask containing a magnet, and then 40 ml of chloroform was added to the three-necked flask.1.5 ml of triethylamine, heated to reflux in an oil bath at 80 C for 3 h, after the reaction is over,The heating was stopped, and the mixture was cooled, and suction filtered to obtain a crude yellow solid powder.The product was washed 3 times with 10 ml of ethanol to obtain a pure product of a yellow solid powder.It was dried and weighed 0.45 g, and the yield was 72.6%

Statistics shows that 5-(Trifluoromethoxy)indoline-2,3-dione is playing an increasingly important role. we look forward to future research findings about 169037-23-4.

Reference:
Patent; Northwest University; Wang Cuiling; Bai Xiao; Zhang Xiaobin; Liu Jianli; (16 pag.)CN110143964; (2019); A;,
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. 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C9H4F3NO3

Weigh5-trifluoromethoxy ruthenium0.95g (0.0041mol),0.85 g (0.0043 mol) of 4-chloroindole anhydride was added to a 100 ml three-necked flask containing a magnet, and then 40 ml of chloroform was added to the three-necked flask.1.5 ml of triethylamine, heated to reflux in an oil bath at 80 C for 3 h, after the reaction is over,The heating was stopped, and the mixture was cooled, and suction filtered to obtain a crude yellow solid powder.The product was washed 3 times with 10 ml of ethanol to obtain a pure product of a yellow solid powder.Dry and weigh 0.92g,The yield was 60.1%.

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 169037-23-4.

Reference:
Patent; Northwest University; Wang Cuiling; Bai Xiao; Zhang Xiaobin; Liu Jianli; (16 pag.)CN110143964; (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., Computed Properties of C10H9Cl2NO

Example 3 Preparation of 5- [2- [4- (1, 2- benzisothiazol-3-yl) -1-piperazinyl] ethyl] -6-chloro-1, 3- dihydro-2H-indol-2-one (Ziprasidone base) In a round bottom flask 1 g of 6-Chloro-5-(2-Chloroethyl)-1,3-Dihydro-2H-Indol-2-One (INT 1), 1.1 g of (3-(1-piperazinyl)1,2-benzisothiazole), 1.46 g of Na2CO3 and 8 ml of 1-ethyl-3-methylimidazolium methyl sulfate were placed, heated to 100 C and stirred for 24 hours. After the completion of the reaction the presence of 5- [2- [4- (1, 2- benzisothiazol-3-yl)-1-piperazinyl] ethyl] -6-chloro-1, 3- dihydro-2H-indol-2-one was confirmed by HPLC. The reaction mixture was cooled to room temperature and 30 ml of methanol was added to precipitate the product. Reaction mixture was stirred for about 1 h and filtered. An amount of 1.8 g of wet crude Ziprasidone base was obtained (Purity 88.0 % was determined by HPLC). A whole sample was further placed in a 50 ml round bottom flask with 20 ml of demineralised water and heated at the 79C for 30 minutes, filtrated and cooled to room temperature. A 2.65 g of precipitated wet Ziprasidone base was dried in a vacuum drier for 1 h at the temperature 50 C and overnight at the room temperature. An amount of 1.03 g of Ziprasidone base was obtained.

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; KRKA; EP1889844; (2008); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 181140-34-1, 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. 181140-34-1, name is (R)-(-)-N-(2,3-Epoxypropyl)phthalimide belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Compounds 3-7 have been synthesized using a procedure originallyreported 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. thenrefluxed for 12 h. The reaction monitored by TLC. Solvent was removed by rotary evaporator under reduced pressure after completionof the reaction.

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, (R)-(-)-N-(2,3-Epoxypropyl)phthalimide, other downstream synthetic routes, hurry up and to see.

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