Month: January 2021

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, Quality Control of 5-Bromoisoindolin-1-one

Step 3 5-(4,4,5 ,5-Tetramethyl-[ 1 ,3 ,2]diotaoxaborolan 2-yl) 2,3-diotahydro-iotasoiotandol-l-one[00356] 5-Bromo-2,3-dihydro-isoindol-l-one (230mg, 1 08mmol), bis(pmacolato)diboron(300mg, 1 18mmol), PdCl2dppf (25mg, 31 mol) 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 ( pp)pl 37 (12H, s), 4 45 (2H, s), 6 38 (IH, br s), 7 87 (IH, d), 7 93 (2H, m)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromoisoindolin-1-one, and friends who are interested can also refer to it.

Reference:
Patent; GALAPAGOS N.V.; WO2007/131991; (2007); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 7477-63-6, name is 7-Chloroisatin, 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 7477-63-6, HPLC of Formula: C8H4ClNO2

General procedure: To a solution of isatin derivative (0.68mmol, 1.0eq) in DMF (4mL) was added K2CO3 (0.68mmol, 1.0eq) at room temperature, the mixture was stirred for about 30min, and then the propargyl bromide (0.75mmol, 1.1eq) was added dropwise. The mixture was stirred for 6-10hat room temperature depending on the isatin derivative used. Upon completion, EtOAc and H2O were added. The aqueous layer was extracted with EtOAc; the combined organic layers were washed with H2O for several times to remove the DMF, and then washed with brine, dried over MgSO4 and evaporated to give the products. Brown solid, yield: 88%, m. p.: 151.7-152.4C, Rf=0.47(petroleum ether/ethyl acetate=2/1). 1H NMR (400MHz, CDCl3) delta 7.67-7.54 (m, 2H), 7.22-7.09 (m, 1H), 4.93 (d, J=2.5Hz, 2H), 2.33 (t, J=2.5Hz, 1H).13C NMR (100MHz, CDCl3) delta 181.76, 157.88, 145.28, 140.55, 125.21, 124.18, 120.60, 117.95, 77.50, 72.94, 31.84

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 7-Chloroisatin, and friends who are interested can also refer to it.

Reference:
Article; Yu, Bin; Qi, Ping-Ping; Shi, Xiao-Jing; Huang, Ruilei; Guo, Hao; Zheng, Yi-Chao; Yu, De-Quan; Liu, Hong-Min; European Journal of Medicinal Chemistry; vol. 117; (2016); p. 241 – 255;,
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Indoline | C8H9N – PubChem

Application of 3484-35-3,Some common heterocyclic compound, 3484-35-3, name is 5-Methylindolin-2-one, molecular formula is C9H9NO, 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 3-substituted-5-benzylidene-2-thioxo-4-thiazolidinone (1-19) (0.003 mol) in 1,4-dioxane (15 mL) was added HC(OEt)3(2 mL) and BF3Et2O (2 mL). The reaction mixture washeated to 80 C and stirring was continued at the same temperature for 4 h. Theresulting 2-ethylthio-3-substituted-5-benzylidene- 4-thiazolium fluoroborate (Ic, IIc) was precipitated, filteredoff, and dried without any additional purification, as starting material forthe following reactions. To a mixture of thiazolium fluoroborate (Ic, IIc) (0.003 mol) and correspondingindolin-2-one (0.003 mol) in acetonitrile (15 mL) was added triethylamine (0.91g, 0.009 mol) dropwise at 25 C, and the mixture was stirred for 4 h at thesame temperature. The orange precipitate was collected and washed with ethylacetate (8 mL). The crude product thus obtained was recrystallized frommethanol or acetone to give compound (1-19).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Methylindolin-2-one, its application will become more common.

Reference:
Article; Wang, Feng; Liu, Zijian; Wang, Jian; Tao, Jun; Gong, Ping; Bao, Xue; Zhao, Yanfang; Wang, Yulin; European Journal of Medicinal Chemistry; vol. 101; (2015); p. 126 – 132;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 20780-72-7, The chemical industry reduces the impact on the environment during synthesis 20780-72-7, name is 4-Bromoisatin, I believe this compound will play a more active role in future production and life.

1H-4-Bromoindole-2,3-dione (452.06 mg, 2 mmol), (trimethylsilyl)diazomethane (2 mL of 2M in toluene, 4 mmol), and triethylamine (0.56 mL, 4 mmol) were dissolved in ethanol (10 mL) and placed under argon. It was stirred at room temperature for 18 hours. The resulting suspension was filtered and the solid was collected and dried under vacuum to reveal 5-bromo-3-methoxyquinolin- 2(111)-one as a white solid (267 mg, 53percent); m.p. 286 – 288 ¡ãC; ?H NMR (400MHz, DMSO-d6) 611.97 (s, 1H), 7.31 (dd,J 8Hz, ,J2 Hz, 1H), 7.15-7.09 (m, 2H), 7.02 (s, 1H), 3.73 (s, 3H); ?3C NMR (100 MHz, DMSO-d6) 6 156.9, 150.0, 135.0, 128.0, 125.8, 119.7, 118.6, 114.6, 109.0, 55.7

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, 4-Bromoisatin, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY; LAVOIE, Edmond J.; BAUMAN, Joseph David; SAGONG, Hye Yeon; ARNOLD, Eddy; PARHI, Ajit; DAS, Kalyan; VIJAYAN, Suyambu Kesava; PATEL, Disha; WO2014/74926; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 114041-16-6, These common heterocyclic compound, 114041-16-6, name is 5,6-Dimethoxyisoindoline, 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.

Compound 416 :In a 10 mL microwave tube, compound 415 (100 mg, 0.23 mmol) was combined with 5,6-dimethoxyisoindoline (42 mg, 0.23 mmol), triethylamine (69 mg, 0.69 mmol) and acetonitrile (2 mL). The solution was irradiated for 30 minutes at 100 C, then diluted with EtOAc and filtered over a short plug of silica gel, rinsing with EtOAc, to afford the intermediate compound 416. HPLC- MS tR = 1.71 min (UV254 nm); Mass calculated for C24H24N8O3: 572.3; Observed m/z: 573.3 (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

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. 17702-83-9, name is 2-(8-Bromooctyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., name: 2-(8-Bromooctyl)isoindoline-1,3-dione

A solution of an alkylbromide of general formula (VIII) (1 eq) in dry DMF (0.5 mL/mmol) was added to a flask suited for microwave heating. The amine (VII) (1 eq) was dissolved in DMF and added to the reaction flask and then K2CO3 (3 eq) was added. The reaction mixture was heated in a microwave oven at 7O0C for 3 h. The reaction was quenched with water, extracted with EtOAc and the organic phase concentrated to dryness, purified by chromatography using appropriate mixture of MeOH/CHCI3/NH3 to afford protected amines of general formula (IX).; Preparation 6: 2-(8-(cvclohexyl(3-morpholinopropyl)amino)octyl)isoindoline-l,3-dione (compound 6). General procedure 3. Starting materials: compounds 1 and 3. 1H-NMR (DMSOd6): delta 7.89-7.82 (m, 4H), 3.58-3.52 (m, 6H), 2.39-2.21 (m, HH), 1.71-1.08 (m, 24H).

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; Topotarget A/S; CHRISTENSEN, Mette Knak; BJOeRKLING, Fredrik; WO2010/142735; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 118289-55-7, These common heterocyclic compound, 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-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.

Refluxed the reaction mixture of 5-(2-Chloro ethyl)-6-chloro oxindole (100 gm), 3-(1-piperazinyl)-1,2-benzisothiazole (104.7 gm), sodium carbonate (92.2 gm), sodium iodide (6.4 gm), tetra butyl ammonium bromide (28 gm) and cyclohexane (1000 ml) till the reaction completes. The reaction mass was cooled to a temperature of 30 C. and filtered the solid. To the wet compound added was water (1000 ml) and continued stirring for 45 minutes. The solid was filtered and washed with water (100 ml). To the water wet compound added acetone (500 ml) and stirred for 2 hours at room temperature. Filtered the compound and washed with acetone (200 ml) and dried at a temperature of 70-75 C. to afford the Crude Ziprasidone base (156.9 gm)

Statistics shows that 6-Chloro-5-(2-chloroethyl)indolin-2-one is playing an increasingly important role. we look forward to future research findings about 118289-55-7.

Reference:
Patent; DR. REDDY’S LABORATORIES LIMITED; DR. REDDY’S LABORATORIES, INC.; US2005/49295; (2005); 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. 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 102359-00-2

[Example 6] (3E)-3-((5-((E)-(1-acetyl-2-oxoindolin-3-ylidene)methyl)furan-2-yl)methylene)-2-oxoindoline-5-carboxylic acid (5) 5-carboxyindolin-2-one (1 equivalent), 3-((5-formylfuran-2-yl)methylene)-N-acetyl-2-oxoindoline (1.2 equivalents) and piperidine (0.2 equivalent) were dissolved in ethanol such that 1 mL of ethanol was used per 1 mumol of the total amount of the compounds, and the resulting mixture was stirred at room temperature for 2 hours. After completion of the reaction, the resulting precipitate was collected by filtration, washed with cooled ethanol several times and dried, whereby a target compound was obtained. 1H-NMR (d6-DMSO, 400 Mz): 9.41 (s, 1H), 9.39 (s, 1H), 8.42 (d, J= 3.91 Hz, 1H), 8.32 (d, J= 3.91 Hz, 1H), 8.07 (s, 1H), 7.98 (s, 1H), 7.92 (d, J= 8.05 Hz, 1H), 7.82 (d, J= 8.05 Hz, 1H), 7.60 (s, 1H), 7.55 (dd, J= 8.21 Hz, 1.72 Hz, 1H), 7.36 (d, J= 7.22 Hz, 1H), 7.26 (d, J= 7.22 Hz, 1H), 6.87 (m, 1H), 2.66 (s, 3H), MS m/z: 440(M)+

The synthetic route of 102359-00-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Theravalues Corporation; EP2130829; (2009); 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. 423116-18-1, name is 2-(4-Oxocyclohexylmethyl)isoindole-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 2-(4-Oxocyclohexylmethyl)isoindole-1,3-dione

Sodium cyanoborohydride (48.5 g, 772 mmol) was added portionwise to a solution of 2-((4-oxocyclohexyl)methyl)isoindoline-1,3-dione (100 g, 389 mmol, Intermediate 50) in AcOH (1.0 L), and the resulting mixture was stirred at rt for 16 h. After this time, the mixture was concentrated, and the concentrate was dissolved in EtOAc. The resulting solution washed twice with a saturated aqueous NaHCO3 solution, dried with anhydrous Na2SO4, filtered, and concentrated to afford the title compound as a colorless solid, which was used in the next step without further purification.

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 423116-18-1.

Reference:
Patent; Janssen Pharmaceutica NV; Goldberg, Steven; Martin, Connor L.; Fennema, Elizabeth G.; Kummer, David A.; Nishimura, Rachel T.; Woods, Craig R.; Wolin, Ronald L.; Jones, William M.; Fourie, Anne M.; Xue, Xiaohua; (180 pag.)US2019/382349; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 957204-30-7, A common heterocyclic compound, 957204-30-7, name is tert-Butyl 6-hydroxyindoline-1-carboxylate, molecular formula is C13H17NO3, 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.

1-(tert-Butoxycarbonyl)-6-hydroxyindoline (400 mg), 2-bromo-4′-phenylacetophenone (515 mg), potassium carbonate (470 mg), and DMF (10 mL) were mixed, and the mixture was stirred at 70C for 12 hours. The reaction mixture was diluted with ethyl acetate (200 mL), and the organic layer was washed with saturated brine. The washed layer was dried over sodium sulfate anhydrate, and solvent was removed by evaporation. The residue was purified by silica gel flash column chromatography (Yamazen Hi-Flash L), to thereby yield the title compound (487 mg). NMR (CDCl3) delta: 1.54(9H,s),3.01(2H,t,J=8.7Hz),3.98(2H,t,J=8.7Hz),5.27(2H,s),6 .56(2H,br s),7.02(1H,d,J=8.3Hz), 7.38-7.43(1H,m), 7.45-7.51(2H,m),7.61-7.65(2H,m), 7.71(2H,d,J=8.5Hz), 8.08(2H,d,J=8.3Hz). MS (ESI) m/z :430 (M+H)+.

The synthetic route of 957204-30-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Daiichi Sankyo Company, Limited; EP2017263; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem