Month: April 2021

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. 104618-31-7, name is 2-(4-Hydroxycyclohexyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Safety of 2-(4-Hydroxycyclohexyl)isoindoline-1,3-dione

The title compound from Step A above (28 g, 114 mmol) was dissolved in dichloromethane (990 mL) and pyridinium chlorochromate (33.6 g, 157 mmol) was added in portions. The reaction mixture was stirred at room temperature for 8 h. Then another batch of pyridinium chlorochromate (10.4 g, 48.6 mmol) was added in portions and stirring at room temperature was continued for 18 h. The reaction mixture was filtered through a pad of Celite and the Celite pad was washed with dichlormethane (400 mL). The combined filtrate was concentrated under reduced pressure and the residue was purified by chromatography on silica using ethyl acetate/n-heptane (60/40) as a mobile phase to afford the title compound as a white solid (24.62 g, 88%)1H-NMR (400 MHz, CDCl3): delta=2.17-2.24 (m, 2H), 2.60-2.71 (m, 4H), 2.80-2.90 (m, 2H), 4.78 (tt, 1H), 7.84-7.88 (m, 2H), 7.97-8.02 (m, 2H)

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; AC Immune, S.A.; US2011/280808; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 611-09-6, name is 5-Nitroindoline-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 611-09-6, category: indolines-derivatives

General procedure: GN/SO3H (80 mg) was added to the 3 mL of EtOH/water (1:1) and dispersed for 30 min. Then, malononitrile (1 mmol), isatin (1 mmol), and dimedone (1 mmol) were added to the mixture and the mixture was heated to reflux and kept at this temperature for an appropriate time. After the time of reaction was completed, water was separated by centrifuging followed by extracting the crude product by ethyl acetate. The solvent was dried using Na2SO4 and removed from the reaction by evaporation with a rotary evaporator. Finally, the crude product was recrystallized in hot ethanol to achieve the pure product. The GN/SO3H nanocomposite was washed and reused several times.

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:
Article; Allahresani, Ali; Taheri, Bahare; Nasseri; Research on Chemical Intermediates; vol. 44; 11; (2018); p. 6979 – 6993;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 32692-19-6, 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. 32692-19-6, name is 5-Nitroindoline, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: We described the synthesis of the compound 1 (Table 2) to illustrate the general procedure for TFA accelerated Petasis three-component reaction. The descriptions of the preparations of all reported compounds are in the Supporting information section. To a magnetically stirred mixture of 5-nitroindoline (0.164 g, 1.0 mmol), 4-tolyboronic acid (0.135 g, 1.0 mmol), and glyoxylic acid monohydrate (0.092 g, 1.0 mmol) in CH2Cl2 (5 ml) was added TFA (20 mul). The mixture was stirred at room temperature for 4 h. After the completion of the reaction (TLC monitoring), half of the solvent was evaporated by means of a rotovap. The resulting solid was filtered through a sintered glass funnel. The collected solid was thoroughly washed with petroleum ether and a small amount of ice water (5 ml), and then dried in vacuo at room temperature for 24 h to afford 0.26 g (83.3 %) of 2-(5-nitroindolin-1-yl)-2-(p-tolyl) acetic acid as a light yellow solid.

The chemical industry reduces the impact on the environment during synthesis 5-Nitroindoline. I believe this compound will play a more active role in future production and life.

Reference:
Article; Zhang, Jing; Yun, Fan; Xie, Rui; Cheng, Chunhui; Chen, Guangyao; Li, Jingxuan; Tang, Pingwah; Yuan, Qipeng; Tetrahedron Letters; vol. 57; 35; (2016); p. 3916 – 3919;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 7699-18-5, A common heterocyclic compound, 7699-18-5, name is 5-Methoxyindolin-2-one, molecular formula is C9H9NO2, 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: 4.4.14 (Z)-3-((2-(3,5-difluorophenyl)-1H-benzo[d]imidazol-6-yl)methylene)-5-methoxyindolin-2-one (5n) Compound 5n was prepared according to the method described for compound 5a, employing aldehyde 11d (129 mg, 0.5 mmol) and 5-methoxyindolin-2-one (12b, 81 mg, 0.5 mmol) to obtain the pure product 5n as a yellow solid (110 mg, 55%); mp: 296-298 C; IR (KBr): 3425, 3165, 2925, 2357, 1673, 1640, 1560, 1410, 1282, 1190, 1120, 942, 866, 745 cm-1; 1H NMR (300 MHz, DMSO-d6): delta 10.69 (bs 1H), 8.04 (s, 1H), 7.91 (s, 3H), 7.75 (s, 1H), 7.62 (s, 2H), 7.47 (t, J = 7.9 Hz, 1H), 7.05-6.87 (m, 2H), 3.79 (s, 3H); 13C NMR (75 MHz, CDCl3 + DMSO-d6): delta 168.8, 164.4 and 161.3 (d, J = 246.1 Hz), 163.7 and 161.7 (d, J = 246.1 Hz) 160.7,154.6, 149.7, 141.2, 137.5, 134.6, 128.7 (d, J = 4.9 Hz), 127.6, 125.4, 124.8, 122.7, 120.6, 118.6, 109.8, 109.4, 105.7, 55.2; MS (ESI): m/z 404 [M + H]+; HRMS (ESI): calcd for C23H16O2N3F2 m/z 404.12308 [M + H]+; found 404.12758.

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; Kamal, Ahmed; Nagaseshadri; Nayak, V. Lakshma; Srinivasulu, Vunnam; Sathish, Manda; Kapure, Jeevak Sopanrao; Suresh Reddy; Bioorganic Chemistry; vol. 63; (2015); p. 72 – 84;,
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. 111992-61-1, name is 2-(3-Bromo-2,2-dimethylpropyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-(3-Bromo-2,2-dimethylpropyl)isoindoline-1,3-dione

Step 3 A suspension of 3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (400 mg, 1.3 mmol, 1.00 equiv), 2-(3-bromo-2,2-dimethylpropyl)-2,3-dihydro-1H-isoindole-1,3-dione (570 mg, 1.95 mmol, 1.50 equiv) and cesium carbonate (847 mg, 2.60 mmol, 2.00 equiv) in NMP (50 mL) was stirred at 100 C. for 12 h under nitrogen atmosphere. It was quenched with water (150 mL). The resulting solution was extracted with ethyl acetate (5*30 mL). The organic layers were combined, dried over sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column eluting with dichloromethane/methanol (10/1). This resulted in 280 mg (41%) of 2-(2-[[4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-2-methylpropyl)-2,3-dihydro-1H-isoindole-1,3-dione as a yellow oil.

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; Principia Biopharma Inc.; Goldstein, David Michael; US8673925; (2014); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 675109-45-2, 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. 675109-45-2, name is 6-Amino-2,3-dihydro-1H-isoindol-1-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

6-Ammnoisoindolin-1-one (15.34 mg, 0.104 mmol) was dissolved in DCM (1.0 mL) along with pyridine (0.039 mL, 0.487 mmol) and DIEA (0.032 mL, 0.183 mmol). Intermediate 14SF (28 mg, 0.061 mmol) in 2 mL of DCM was added dropwise, and the reaction mixture was stirred at room temperature for 50 minutes. The reaction was quenched with 1.0 N HC1 (0.5 mL). All solvent was removed under vacuum. The crudewas dissolved in DMSO/THF (2:1, 6 mL) and purified via preparative LC/MS (method C,40-100% B over 18 mm, then a 5-mm hold at 100% B). Fractions containing the desired product were combined and dried via centrifugal evaporation to yield Example 178 (10.7 mg, 31% yield). ?H NMR (500MHz, DMSO-d6) 8.72 (s, 1H), 8.56 (s, 1H), 8.51 (br. s., 1H), 7.86 (d, J=10.7 Hz, 2H), 7.81 (br. s., 2H), 7.61 (br. s., 1H), 7.46 (d, J=5.8 Hz, 1H),5.48-5.38 (m, 1H), 4.54 (d, J12.2 Hz, 1H), 4.41 (dd, J=12. 1, 7.2 Hz, 1H), 4.29 (s, 2H),4.08 (s, 3H), 3.64 (dd, J15.9, 9.8 Hz, 1H), 3.36 (d, J=13.7 Hz, 1H), 2.62 (s, 3H);LC-MS: method C, 2 to 98% B. RT = 2.21 mm, MS (ESI) m/z: 572.30 (M+H).Analytical HPLC purity (method B): 100%.

The synthetic route of 6-Amino-2,3-dihydro-1H-isoindol-1-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; ZHANG, Xiaojun; PRIESTLEY, Eldon Scott; HALPERN, Oz Scott; JIANG, Wen; REZNIK, Samuel Kaye; RICHTER, Jeremy M.; (545 pag.)WO2018/13776; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 17702-83-9, 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. 17702-83-9, name is 2-(8-Bromooctyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: 0.91 g (3.6 mmol) N-(2 -bromoethyl) phthalimide was dissolved 20 mL DMF, added 0.53 g (3 mmol)1-benzylpiperazine, 0.62 g (4.5 mmol) K2CO3, heated to 60-70 ¡ãC reacted for 4 h, TLC detection, until the benzylpiperazinewas complete reaction. 30 mL of water was added, extracted three times withethyl acetate (20 mL¡Á 3), the organic layer was extracted four times (30mL ¡Á 4)with saturated brine, dried with anhydrous magnesium sulfate, and the solventwas distilled off under reduced pressure, cooled to room temperature, silicagel column chromatography (100-200 mesh silica gel, eluent petroleum ether:ethyl acetate = 1:1 – 1: 4) to give 0.7 g (67percent yield) as a white solid. #10;

The synthetic route of 2-(8-Bromooctyl)isoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Si, Weijie; Zhang, Tao; Zhang, Lanxiang; Mei, Xiangdong; Dong, Mengya; Zhang, Kaixin; Ning, Jun; Bioorganic and Medicinal Chemistry Letters; vol. 26; 9; (2016); p. 2380 – 2382;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 3891-07-4, name is 2-(2-Hydroxyethyl)isoindoline-1,3-dione, molecular formula is C10H9NO3, 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. SDS of cas: 3891-07-4

A solution of 126 (5 g, 26 mmol) in DMF (50 mL) was treated with sodium hydride (1.1 g, 32 mmol, 70 % dispersed in mineral oil) for 30 minutes at room temperature, followed by addition of BnBr (6.7 g, 39 mmol). After additional 1 hour, the reaction was quenched by water (200 mL) and extracted with ethyl acetate (4×50 mL). The combined organic layer was washed with brine (3×50 mL), dried over anhydrous sodium sulfate and concentrated under vacuum to give a residue, which was purified by a silica gel column, eluted with 10 % – 20 % ethyl acetate in petroleum ether to afford 127 as a white solid (4.8 g, 65 %).(ES, m/z) [M+H]+ 282.0; 1H NMR (300 MHz, CDC13) delta 7.85 – 7.88 (m, 2H), 7.71 – 7.74 (m, 2H), 7.25 – 7.31 (m, 5H), 4.55 (s, 2H), 3.95 (t, / = 6.0 Hz, 2H), 3.74 (t, / = 6.0 Hz, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3891-07-4, its application will become more common.

Reference:
Patent; ALECTOS THERAPEUTICS INC.; MERCK SHARP & DOHME CORP.; CHANG, Jiang; LIU, Kun; MCEACHERN, Ernest J.; MU, Changwei; SELNICK, Harold G.; SHI, Feng; VOCADLO, David J.; WANG, Yaode; WEI, Zhongyong; ZHOU, Yuanxi; ZHU, Yongbao; WO2012/62157; (2012); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 100510-65-4, These common heterocyclic compound, 100510-65-4, name is 6-Amino-3,3-dimethylindolin-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.

To a’ -solution of 110 mg di-imidazol-1-yl-methanone and 6mg imidazole- in 2. ml tetrahydrofuran a solution of- 100 mg .6-amino-3,3-dimethyl-l, 3-dih’ydro-indol-2-one in. 1. mltetrahydrofuran was slowly added at 0C. After stirringat 0C’. for ‘3’0 minutes and 1 hour at room temperature 103mg . ” . 2-methyl-2-[(quinolin-4-ylmethyl)-amino]-propionicacid methyl ester were added and the reaction mixture was ,allowed to warm up to room temperature.. After 16 hours.stirring at .room ‘temperature the solution was heated for1 -hour -“at 70C.: After cooling to room temperature thesolvent of the mixture was removed .under reduced pressureand the residue was purified by preparative HPLC (C18reverse phase’?? column, ‘ elution ? with a water/ acetonitrile gradient with CL .%’? “trifluoroacetic acid). Lyop.hiliza.tion of the’-solution’yielded -a. white -solid, that was purified, .in addition.’by. flash chromatography on silica gel with a ‘d’ichloro-methane/methanol’ . gradient. The . fractions containing ‘the product? were’ combined and evaporated to yield ? – a . . white . solid.?Yield: 7.5 mg ‘ ?,?…M+H+ measured = ‘429 ‘1H-NMR (500 MHz’, ? DMSO/TMS).: d .= 10.50 (s, 1H) ; 8.87 (d,?1H); 8.25 (d, 1H) ; 8.09-(d, 1H) ; 7.82 (t, 1H) ; 7.70 (t,1H); 7.63 (d, 1H) ; 7.42 (d, IE).; 7.07 (d, 1H) ; 7.01 (s,1H); 5.14 (s, 2H); 1.43 (s, 6H); 1.29 (s, 6H)

The synthetic route of 100510-65-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AVENTIS PHARMA S.A.; WO2006/10642; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 56341-37-8,Some common heterocyclic compound, 56341-37-8, name is 6-Chlorooxindole, molecular formula is C8H6ClNO, 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.

To the mixture of 6-chloro-2-oxindole (5.3 g, 32 mmol) (Crescent) and 3-chloro-4-fluorobenzaldehyde (5 g, 32 mmol) (Aldrich) in methanol (200 mL) was added piperidine (2.7 g, 32 mmol) (Aldrich) dropwise. The mixture was then heated at 50 C. for 3 h. After cooled to 4 C., the mixture was filtered and resulting precipitate was collected, dried to give E/Z-6-chloro-3-(3-chloro-4-fluoro-benzylidene)-1,3-dihydro-indol-2-one as a yellow solid (Yield 8 g, 82%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Chlorooxindole, its application will become more common.

Reference:
Patent; Bartkovitz, David Joseph; Chu, Xin-Jie; Ding, Qingjie; Graves, Bradford James; Jiang, Nan; Zhang, Jing; Zhang, Zhuming; US2011/130398; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem