Month: February 2021

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. 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. name: 5-(Trifluoromethoxy)indoline-2,3-dione

General procedure: A mixture of bisarylidenepiperidin-4-one (1.36 mmoL), isatin (2.72 mmoL) and L-phenylalanine (2.72 mmoL) were heated with stirring in [bmim]Br medium (3 mL) for 1 h at 100 C. After completion of the reaction (TLC), ethyl acetate (2 x 5 mL) was added and the reaction mixture was stirred for 10 min. The organic layer was removed under reduced pressure and the crude product was purified by column chromatography (ethyl acetate:hexane v/v 3:7). 5′-Benzyl-4′-(m-tolyl)-5-(trifluoromethoxy)spiro[3,2′]oxindolopyrrolidino-4′-(methylphenyl)-1?-styryl-5-benzylidene-spiro[3′.3?]piperidin-4?-one (5h): Melting point 234-236 C; white solid, 88%; 1H-NMR (CDCl3, 400 MHz): delta/ppm 4.99 (d, J = 14.5 Hz, 1H), 4.63-4.68 (m, 1H), 4.34 (d, J = 10.0 Hz, 1H), 3.77 (d, J = 14.00 Hz, 1H), 3.68 (d, J = 15.00 Hz, 1H), 3.38-3.47 (dd, J = 15 Hz, 1H), 3.00-3.03 (dd, J = 14.5 Hz,1H), 2.72-2.76 (m, 1H), 2.56 (d, J = 14.0 Hz, 1H), 2.33 (s, 3H), 2.27 (s, 3H), 6.60 (d, J = 14.5 Hz, 2H), 6.79-7.71 (m, 21H, Ar); 13C-NMR (CDCl3, 100 MHz): delta/ppm 21.1, 21.4, 39.4, 47.4, 52.8, 52.9, 61.1, 66.9, 70.8, 100.8, 109.5, 119.5, 120.9, 121.5, 122.4, 123.9, 124.3, 126.3, 128.4, 128.5, 128.6, 129.2, 129.4, 129.5, 130.5, 131.7, 133.6, 135.3, 136.2, 136.8, 138.3, 138.5, 138.8, 139.7, 139.8. 140.0, 144.3, 179.7, 197.1. EI-MS: m/z 739 (M+). Anal. Calcd for C46H40F3N3O3: C, 74.68; H, 5.45; N, 5.68. Found: C, 74.77; H, 5.55;N, 5.81.

The synthetic route of 169037-23-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Arumugam, Natarajan; Almansour, Abdulrahman I.; Kumar, Raju Suresh; Govindasami, Periyasami; Al-thamili, Dhaifallah M.; Krishnamoorthy, Rajapandian; Periasamy, Vaiyapuri Subbarayan; Alshatwi, Ali A.; Mahalingam; Thangamani, Shankar; Menendez, J. Carlos; Molecules; vol. 23; 5; (2018);,
Indoline – Wikipedia,
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These common heterocyclic compound, 2058-72-2, name is 5-Bromo-1-methylindoline-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. Quality Control of 5-Bromo-1-methylindoline-2,3-dione

General procedure: A solution of isatin derivatives 1 (0.4 mmol), dienones 2 (0.6 mmol) and sarcosine (0.8 mmol) in CH3CN (10.0 mL) was stirred at 80 oC for 24 h. After completion of the reaction, as indicated by TLC, the reaction mixture was directly subjected to flash column chromatography on silica gel (petroleum ether/EtOAc = 5:1~3:1) to furnish the corresponding products 3.

The synthetic route of 5-Bromo-1-methylindoline-2,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liu, Xiong-Li; Yang, Chao; Zhang, Wen-Hui; Zhou, Gen; Ma, Xi-Tao; Lin, Bing; Zhang, Min; Zhou, Ying; Feng, Ting-Ting; Tetrahedron Letters; vol. 57; 12; (2016); p. 1385 – 1389;,
Indoline – Wikipedia,
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Electric Literature of 7477-63-6, These common heterocyclic compound, 7477-63-6, name is 7-Chloroisatin, 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 1 (0.4 mmol), 2 (0.4 mmol), Na2CO3 (0.8 mmol) and TBHP (0.4 mmol) in DMF (4 mL) was stirred at rt for 2 h. Then, the mixture was poured into ice-water, acidified with 1 N HCl aq. (6 mL). The mixture was extracted with ethyl acetate (20 mL x 3). The combined organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by silica gel flash column chromatography to give desired products..

Statistics shows that 7-Chloroisatin is playing an increasingly important role. we look forward to future research findings about 7477-63-6.

Reference:
Article; Wu, Jun; Zhang, Hui; Ding, Xiao; Tan, Xuefei; Shen, Hong C.; Chen, Jie; He, Weimin; Deng, Hongmei; Song, Liping; Cao, Weiguo; Journal of Fluorine Chemistry; vol. 220; (2019); p. 54 – 60;,
Indoline – Wikipedia,
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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. 87-48-9, name is 5-Bromoindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 87-48-9

General procedure: Isatin or 5-substituted isatin (7 mmol) and K2CO3 (10 mmol) were added to a dry CH3CN solution (25 mL) and stirred for 30 min at RT. Methyl iodide or benzyl chloride (7.5 mmol) was added to the solution and then refluxed at 80C for 3 hour. The mixture was cooled to RT and the solvent was removed. The residue was dissolved in CH2Cl2(30 mL) and then washed with H2O (3×30 mL). The organic extracts were dried over anh Na2SO4 and concentrated to give the crude brown solid. The purification of the crude solid using flash-column chromatography (silica gel, hexane/EtOAc (2:1) gave the pure compounds 3a-g.

According to the analysis of related databases, 87-48-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Phutdhawong, Weerachai; Rattanopas, Sopita; Sirirak, Jitnapa; Taechowisan, Thongchai; Phutdhawong, Waya S.; Oriental Journal of Chemistry; vol. 35; 2; (2019); p. 723 – 731;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 222036-66-0, These common heterocyclic compound, 222036-66-0, name is 5-Aminoisoindolin-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.

General procedure: Isoindolin-1-one (200 mg, 1.50mmol) was dissolved in super-dry DMSO (4 mL), and Cs2CO3 (1215 mg, 3.75 mmol), CuI (58 mg, 0.30mmol) and N1,N2-dimethylethane-1,2-diamine (27 mg, 33 muL, 0.30 mmol) were added to the solution.The resulting mixture was stirred at room temperature for 10 min, after which iodobenzene (2.25mmol) was added. Then the mixture was heated to 120 C. When TLC showed that isoindolin-1-onehad been fully converted, the reaction was stopped. The mixture was extracted with ethyl acetate (20mL) and H2O (10 mL). The water phase was re-extracted with ethyl acetate (20 mL). The organic layerwas combined and washed with brine (10 mL). Then the solution was dried over anhydrous MgSO4,filtered and concentrated, and the crude residue was purified by flash chromatography over silica gelusing CH2Cl2/CH3OH as the gradient elution to afford the title compounds.

Statistics shows that 5-Aminoisoindolin-1-one is playing an increasingly important role. we look forward to future research findings about 222036-66-0.

Reference:
Article; Wang, Yixuan; Wang, Huiqiang; Jiang, Xinbei; Jiang, Zhi; Guo, Tingting; Ji, Xingyue; Li, Yanping; Li, Yuhuan; Li, Zhuorong; Molecules; vol. 24; 5; (2019);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 552330-86-6, These common heterocyclic compound, 552330-86-6, name is 5-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.

A mixture of 5-bromoisoindolin-1-one 1 (5 g, 23.6 mmol), THF (50 mL), 4-dimethylaminopyridine (288 mg, 2.36 mmol) and di-tertbutyl dicarbonate (8 g, 35.4 mmol) was stirred for overnight at room temperature. The resulting mixture was concentrated under reduced pressure, diluted with ethyl acetate, washed with 10% citric acid. The organic layer was dried over Na2504, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel, eluting with ethyl acetate/heptane (1:1) to afford the compound 2 (7.1 g, 96%) as a white solid. LC/MS (ESI+): mlz 313.2 (M+H).

Statistics shows that 5-Bromoisoindolin-1-one is playing an increasingly important role. we look forward to future research findings about 552330-86-6.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; CHEN, Huifen; CHU, Yanyan; DO, Steven; ESTRADA, Anthony; HU, Baihua; KOLESNIKOV, Aleksandr; LIN, Xingyu; LYSSIKATOS, Joseph P.; SHORE, Daniel; VERMA, Vishal; WANG, Lan; WU, Guosheng; YUEN, Po-wai; WO2015/52264; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 496-12-8, 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. 496-12-8, name is Isoindoline, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A solution of amine (0.2 mmol) and MnCl2¡¤4H2O (5.9 mg, 15 mol%) in DMF (1.0 mL) was stirred in a sealed microwave reaction tube under an atmosphere of argon at 150 C for 10 h. The mixture was cooled to r.t., and water (10 mL) was added; the mixture was extracted with EtOAc (3 ¡Á 15 mL). The combined organic layers were dried (anhyd Na2SO4), the solvent was evaporated under vacuum, and the crude product was purified by preparative TLC (silica gel, petroleum ether/EtOAc) to obtain the pure product.

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

Reference:
Article; Ma, Juan; Zhang, Jingyu; Gong, Hang; Synthesis; vol. 51; 3; (2019); p. 693 – 703;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 356068-93-4, name is (Z)-5-((5-Fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid, molecular formula is C16H13FN2O3, 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. Formula: C16H13FN2O3

Example 6 Preparation of 3-{5-[5-fluoro-2-oxo-1 ,2-dihydro-indol-(3Z)-ylidenemethyl]- 2,4-dimethyl-1 H-pyrrole-3-carbonyl}amino-propionic acid methyl ester. 5-[5-fluoro-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carbox- ylic acid (300 mg, 1 mmol) and 8 ml of DMF were stirred at room temperature while 1-Ethyl-3-(3-dimethyllaminopropyl)carbodiimide hydrochloride (384 mg, 2 mmol), hydroxybenzotriazole (162 mg, 1.2 mmol), triethylamine (404 mg, 4 mmol) and beta-alanine methyl ester hydrochloride (168.6 mg, 1.2 mmol) were added. The mixture was stirred for 20 hours at room temperature. The mixture was diluted with 400 mL of brine. The solids were collected by vacuum filtration, washed with water and dried under vacuum to give 2-{5-[5-fluoro-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-car- bonyljamino-propionic acid methyl ester (333 mg, 87% yield) as a yellow solid. 1H NMR (DMSO-d6)delta2.39 (s, 3H, pyrrole-CH3), 2.41 (s, 3H, pyrrole-CH3), 2.58 (d, J= 8.0 Hz, 2H, CH2CO), 3.50 (m, 2H, NCH2), 3.63 (s, 3H, COOCH3), 6.84 (dd, J= 4.0 and 8.0 Hz, 1H, Ar-H), 6.92 (td, J= 4.0 and 8.0 Hz, 1H, Ar-H), 7.70 (s, 1H, vinyl-H), 7.67 (t, J= 4.0Hz, 1H, CONH), 7.75 (dd, J= 4.0 and 8.0 Hz, 1H1 Ar-H), 10.88 (s, 1 H, indolinone-NH), 13.66 (s, 1H, pyrrole-NH). LC-MS (m/z) 386 (M+1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 356068-93-4, its application will become more common.

Reference:
Patent; SHENZEN CHIPSCREEN BIOSCIENCE, LTD.; WO2009/14941; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 317-20-4, name is 7-Fluoroisatin, 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 317-20-4, Formula: C8H4FNO2

General procedure: A mixture of isatins 1 (1 mmol), substituted 1H-pyrazol-5-amine 2 (1 mmol), 6-aminopyrimidine-2,4(1H,3H)-dione 3 or 6-amino-1,3-dimethylpyrimidine-2,4(1H,3H)-dione 5 (1 mmol), H2O(6 mL), and HOAc (2 mL) was placed in a 25-mL flask andstirred at 90 C (monitored by thin layer chromatography (TLC)) for about 7 h. Afterreaction completion, the mixture was cooled to room temperature and the precipitateobtained by filtration. Compounds 4 or 6 were further purified by recrystallizationfrom DMF.

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, 7-Fluoroisatin, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Dai, Lei; Mao, Kaimin; Pan, Zhengbing; Rong, Liangce; Research on Chemical Intermediates; vol. 45; 2; (2019); p. 769 – 788;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 2058-74-4, 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 2058-74-4 as follows.

A solution of N-methylisatin (322 mg, 2.0 mmol), phenylacetylene (306 mg, 3.0 mmol), CuI (76 mg, 0.4 mmol), and Cs2CO3 (978 mg, 3.0 mmol) in CH3CN (4.0 mL) was stirred at room temperature for 18 h. After aqueous extractive workup and column chromatographic purification process (CH2Cl2/EtOAc, 15:1) 1a was obtained as a pale yellow solid, 347 mg (66%).1-12 Other compounds were prepared similarly,1-12 and the propargylic alcohols were used in the next hydrogenation step without further identification process.

According to the analysis of related databases, 2058-74-4, the application of this compound in the production field has become more and more popular.

Reference:
Note; Seo, Da Young; Min, Beom Kyu; Roh, Hwa Jung; Kim, Jae Nyoung; Bulletin of the Korean Chemical Society; vol. 38; 10; (2017); p. 1231 – 1234;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem