Tag: M.W=100-200

Reference of 774-47-0, 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. 774-47-0, name is 5,6-Difluoroindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Dissolved 5,6-difluoroindoline-2,3-dione (14) (0.714 g,3.899 mmol) in 25 mL of MeOH, under argon atmosphere, and refluxedthe resulting solution at 60 C for 15 min. p-toluenesulfonyl hydrazide(0.807 g, 4.333 mmol), dissolved in 5 mL of MeOH, was added to thehot solution in one portion. The resulting reaction mix was refluxed, at60 C for 24 h. Consequently, the reaction mixture was allowed to coolto room temperature, gradually, and filtered to afford a yellow precipitate.The precipitate was dissolved in 30 mL of distilled water,containing sodium hydroxide (0.331 g, 8.275 mmol), and heated to64 C for 4 h. Solid carbon dioxide was added to the cooled reactionmixture to precipitate the pure diazo product, UIAA-II-187 (15), whichwas filtered and concentrated. 52% yield. 1H NMR (300 MHz, DMSO)delta = 10.83 (bs, 1H), 7.64 (dd, J = 7.82, 10.65 Hz, 1H), 6.96 (dd,J = 7.07, 10.83 Hz, 1H). 19F NMR (282 MHz, DMSO) delta = -142.37 (m,1F), -147.72 (ddd, J = 6.96, 10.71, 21.72 Hz, 1F). HRMS (ESI) calculatedfor (M + H+) 196.0317, found 196.0323. Retention time(analytical HPLC) = 14.9 min.

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, 5,6-Difluoroindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Aguirre, Arturo L.; Chheda, Pratik R.; Groves, Natalie P.; Held, Hailey A.; Hiasa, Hiroshi; Kerns, Robert J.; Lentz, Sarah R. C.; Bioorganic and medicinal chemistry; (2020);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 611-09-6,Some common heterocyclic compound, 611-09-6, name is 5-Nitroindoline-2,3-dione, molecular formula is C8H4N2O4, 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: 30 mg of SiO2_g-C3N4 nanocomposite was dispersed in aqueous media (3 ml) for 30 min and dimedone or 4-hydroxycoumarin (1 mmol), malononitrile (1 mmol) and isatin (1.0 mmol) were added to the mixture. Then, the mixture was stirred at reflux conditions for an appropriate time, while the reaction progress was monitored by thin layer chromatography (TLC). After the reaction was completed, ethyl acetate was employed for the extraction of crude product and the products were dried over anhydrous Na2SO4. The solvent was evaporated followed by recrystallizing of the crude product in hot ethanol, and pure products were identified by IR, 1H and 13C NMR spectral data. The SiO2_g-C3N4 nanocatalyst was washed with EtOH, dried and reused for the next run.

The synthetic route of 611-09-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Allahresani, Ali; Taheri, Bahare; Nasseri, Mohammad Ali; Research on Chemical Intermediates; vol. 44; 2; (2018); p. 1173 – 1188;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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 496-12-8 as follows. HPLC of Formula: C8H9N

General procedure: A solution of N-heterocycle compound (0.2 mmol) and graphene oxide (GO) (8 mg) in N,N-dimethylformamide(1.0 mL) was stirred in a sealed tube under an atmosphere of argon at 150 C for 18 h. After being cooled to room temperature,the reaction mixture was filtered and washed with ethyl acetate (20 mL). Afterward, 10 mL water was added tothe solution and extracted with ethyl acetate (3 × 15 mL), the combined organic layers were dried over anhydrous Na2SO4.The solvent was evaporated under vacuum and the crude product was purified by preparative thin-layer chromatography (TLC) on silica gel with petroleum ether and ethyl acetate to achieve the pure product.

According to the analysis of related databases, 496-12-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ma, Juan; Zhang, Jingyu; Zhou, Xiao; Wang, Jiawei; Gong, Hang; Journal of the Iranian Chemical Society; vol. 15; 12; (2018); p. 2851 – 2860;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 222036-66-0, name is 5-Aminoisoindolin-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 222036-66-0, COA of Formula: C8H8N2O

A mixture of 3-(8-(5,6-dimethoxypyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)benzoic acid (100 mg, 0.26 mmol), 5-aminoisoindolin-1-one (38 mg, 0.26 mmol), 1-methyl-1H-imidazole (84 mg, 1.02 mmol) and EDCI (196 mg, 1.02 mmol) in DMF (3 mL) was stirred for 16 h at room temperature. Ethyl acetate (5 mL) and water (5 mL) were added. The organic layer was separated and the aqueous phase was extracted with ethyl acetate (20 mL). The organic phases were combined and washed with brine (10 mL) then dried over Na2SO4. The residue was concentrated and triturated with MeOH (2 mL) to give 3-(8-(5,6-dimethoxypyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)-N-(1-oxoisoindolin-5-yl)benzamide (26 mg, 20percent) as a yellow solid. 1H NMR (300 MHz, DMSO): delta 10.68 (s, 1H), 9.97 (s, 1H), 8.61 (s, 1H), 8.52 (s, 1H), 8.44 (s, 1H), 8.24-8.08 (m, 4 h), 7.82-7.64 (m, 4 h), 7.41 (d, 1H, J=8.7 Hz), 7.11 (d, 1H, J=8.4 Hz), 4.39 (s, 2H), 4.02 (s, 3H), 3.76 (s, 3H). LC-MS: [M+H]+, 521.9, tR=1.434 min, HPLC: 96.12percent at 214 nm, 96.79percent at 254 nm, tR=3.673 min.

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; Hoffmann-La Roche Inc.; Hermann, Johannes Cornelius; Kuglstatter, Andreas; Lucas, Matthew C.; Padilla, Fernando; Wanner, Jutta; Zhang, Xiaohu; US2013/109661; (2013); 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. 611-09-6, name is 5-Nitroindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 5-Nitroindoline-2,3-dione

Example 17 (S)-3,5-Dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)- phenyl)-2-(2-(5-(methylsulfonamido)-2,3-dioxoindolin-1 -yl)acetoxy)ethyl)- pyridine 1 -oxide (Compound 99) Scheme 17 Step 1. Preparation of 5,5-dimethyl-5′-nitrospiro[[1 ,3]dioxane-2,3′- indolin]-2′-one (94) A mixture of 5-nitroindoline-2,3-dione (305 mg, 1 .587 mmol), 2,2-dimethylpropane-1 ,3-diol (165 mg, 1 .587 mmol) and p-toluenesulfonic acid monohydrate (catalytic amount) in cyclohexane (9 ml) was stirred at reflux temperature (removing water by a Dean-Stark apparatus) for 6 hours. The reaction was cooled to room temperature and the solid was recovered by filtration and washed with petroleum ether, affording 5,5-dimethyl-5′-nitrospiro[[1 ,3]dioxane-2,3′-indolin]-2′- one (481 mg). that was used as such in the following step. MS/EST 279.0 [MH]+.

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 611-09-6.

Reference:
Patent; CHIESI FARMACEUTICI S.P.A.; ARMANI, Elisabetta; AMARI, Gabriele; CAPALDI, Carmelida; CARZANIGA, Laura; LA PORTA, Elena; GUALA, Matilde; WO2013/57013; (2013); 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. 496-12-8, name is Isoindoline, A new synthetic method of this compound is introduced below., Safety of Isoindoline

methyl 1-(6-chloropyrimidin-4-yl)piperidine-4-carboxylate 15 (500 mg, 1.96mmol), 2,4-difluorophenol (1.02 g, 7.82mmol) and Cs2CO3 (2.56 g, 7.82mmol) were combined in a microwave vial, and NMP (11mL) was added. The resulting solution was heated to 180C with microwave irradiation for 20 min, after which time solids were removed by filtration, and crude residue was purified by RP-HPLC. Fractions containing product were extracted with 3:1 chloroform/IPA. Solvents were dried with MgSO4, filtered and concentrated to give product 16 as a brown, spongy solid (320 mg, 49%). 1H NMR (400MHz, CDCl3) delta 8.27 (s, 1H), 7.20 – 7.14 (m, 1H), 6.97 – 6.88 (m, 2H), 6.05 (s, 1H), 4.27 – 4.24 (m, 2H), 3.17 – 3.10 (m, 2H), 2.70 – 2.63 (m, 1H), 2.06 – 2.02 (m, 2H), 1.82 – 1.73 (m, 2H); 13C NMR (101MHz, CDCl3) delta 179.03, 169.60, 163.87, 161.28, 161.18, 158.82, 158.72, 157.72, 156.01, 155.89, 153.51, 153.38, 136.62, 124.63, 124.54, 111.68, 111.64, 111.45, 111.41, 105.68, 105.46, 105.41, 105.19, 85.88, 43.83, 40.68, 27.46 (multiple Cs coupled to F). LCMS (215nm) RT=0.764 min (>98%); m/z 336.2 [M+H]. Compound 16 (50 mg, 0.15mmol) and isoindoline (0.028mL, 0.22mmol) were dissolved in DMF (2mL), and DIPEA (0.13mL, 0.75mmol) and HATU (85 mg, 0.22mmol) were added. The resulting solution was stirred at r.t. for 1 h, after which time crude residue was purified directly by RP-HPLC. Fractions containing product were basified with sat. NaHCO3, and extracted with 3:1 chloroform/IPA. Organic extracts were filtered through a phase separator and concentrated to give product 17e as a light brown solid (42 mg, 65%). 1H NMR (400MHz, CDCl3) delta 8.26 (s, 1H), 7.32 – 7.27 (m, 4H), 7.20 – 7.14 (m, 1H), 6.96 – 6.87 (m, 2H), 6.09 (s, 1H), 4.93 (s, 2H), 4.82 (s, 2H), 4.48 – 4.41 (m, 2H), 3.10 – 3.03 (m, 2H), 2.83 – 2.75 (m, 1H), 1.93 – 1.88 (m, 4H); 13C NMR (101MHz, CDCl3) delta 173.19, 169.70, 163.99, 161.12, 161.02, 158.67, 158.57, 157.87, 156.02, 155.90, 153.52, 153.39, 136.74, 136.70, 136.62, 136.58, 136.54, 136.01, 128.10, 127.72, 124.64, 124.62, 124.54, 124.52, 123.22, 122.70, 111.55, 111.51, 111.32, 111.29, 105.56, 105.34, 105.29, 105.07, 85.94, 52.51, 52.47, 43.96, 40.47, 27.59 (multiple Cs coupled to F). LCMS (215nm) RT=0.950 min (>98%); m/z 437.2 [M+H]

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; Bender, Aaron M.; Weiner, Rebecca L.; Luscombe, Vincent B.; Cho, Hyekyung P.; Niswender, Colleen M.; Engers, Darren W.; Bridges, Thomas M.; Jeffrey Conn; Lindsley, Craig W.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 11; (2017); p. 2479 – 2483;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application 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.

To a solution of 2,3-dihydro-1 H-isoindole (0.3 mL) in dichloromethane (5 mL)Triethylamine (0.7 mL)And the mixture was ice-cooled to 0 C.,2-Bromoacetyl bromide (0.4 mL) was added dropwise, followed by stirring at room temperature for 18 hours.Water was added to the reaction solution, the mixture was extracted with dichloromethane and washed with saturated brine.The organic layer was dried over sodium sulfate and the solvent was distilled off under reduced pressure to obtain a residue.Purification by silica gel column chromatography (hexane-ethyl acetate)2-Bromo-1- (2,3-dihydro-1 H-isoindol-2-yl)Ethan-1-one281 mg (yield 47%) was obtained.

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:
Patent; NATIONAL CENTER FOR GERIATRICS AND GERONTOLOGY; YANAGISAWA, KATSUHIKO; KAWAI, AKIYOSHI; (139 pag.)JP2017/171619; (2017); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 13861-75-1, These common heterocyclic compound, 13861-75-1, name is Spiro[cyclopropane-1,3′-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.

[0272] To a cooled (0C) solution of spiro[cyclopropane-l,3′-indolin]-2′-one (prepared according to methods described in J. Med. Chem. 1987, 824-829; J. Med. Chem. 1992, 163-172; U.S. Patent 5,182,397) (1.0 g, 6.21 mmol) in NN-dimethylformamide (5 mL), was added sodium hydride (0.149 g, 6.21 mmol), followed by addition of l-bromo-3-chloropropane (0.733 mL, 7.45 mmol, d = 1.6). After stirring at room temperature for 18 hours, the reaction mixture was diluted with ethyl acetate (100 mL), washed with dilute citric acid, water and brine. The organic phase was dried over MgS04, filtered and isolated by Biotage flash chromatography (10-40% ethyl acetate/hexanes) to obtain the title compound (1.1 g, 68%); ¾ NMR (DMSO-i 6): delta 1.50-1.54 (m, 2H), 1.56-1.61 (m, 2H), 2.01- 2.15 (m, 2H), 3.67 (t, 2H, J= 6.4 Hz), 3.86 (t, 2H, J= 6.8 Hz), 6.97-7.03 (m, 2H), 7.11 (d, 1H, J= 8 Hz), 7.22-7.27 (m, 1H); MS for Ci3H14ClNOm/z 236.04 (M+H)+.

The synthetic route of 13861-75-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALTOS THERAPEUTICS, LLC; LUEHR, Gary, W.; SUNDARAM, Arathi; JAISHANKAR, Priyadarshini; PAYNE, Philip, W.; DRUZGALA, Pascal; WO2011/160084; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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 1127-59-9 as follows. Recommanded Product: 1127-59-9

General procedure: A solution of isatin derivatives 1 (0.4 mmol), 3-methyl-4-nitro-5-alkenyl-isoxazoles 2 (0.6 mmol) and proline or thioproline or sarcosine (0.8 mmol) in 10.0 mL of CH3CN at 80 °C 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/EtOAc5:1-3:1) to furnish the corresponding products 3-5.

According to the analysis of related databases, 1127-59-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Liu, Xiong-Wei; Yao, Zhen; Yang, Jun; Chen, Zhi-Yong; Liu, Xiong-Li; Zhao, Zhi; Lu, Yi; Zhou, Ying; Cao, Yu; Tetrahedron; vol. 72; 10; (2016); p. 1364 – 1374;,
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.

A mixture 6-chloroindolin-2-one (100 mg, 0.60 mmol), 3-(3,3,4,4- tetramethylborolan-l-yl)pyridine (184 mg, 0.90 mmol), Pd2dba3 (5.4 mg, 0.0060 mmol) and powdered K3PO4 (252 mg, 1.2 mmol) in w-BuOH (2 mL) was degassed by evacuation and refilling with Ar. Dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2- yl)phosphine (11.4 mg, 0.024 mmol) was added under the atmosphere of Ar. The reaction mixture was sealed and heated with stirring under microwave irradiation at 100 0C for 99 min. Later the reaction was cooled to rt and treated with degassed H2O (0.25 mL). The mixture was reheated under microwave irradiation at 110 0C for 1 h. The crude reaction mixture was concentrated under reduced pressure and purified by flash chromatography on silica gel using MeOH (0 to 6 %) in DCM as the eluent to provide the title compound as a pale yellow solid (100 mg, 80 %). %). 1H NMR (400 MHz, CD3OD) delta ppm 8.77 (d, J=I.52 Hz, 1 H), 8.52 (dd, J=4.80, 1.52 Hz, 1 H), 8.05 – 8.10 (m, 1 H), 7.52 (dd, J=7.33, 4.80 Hz, 1 H), 7.39 (d, J= 7.6 Hz, 1 H), 7.30 (dd, J=7.71, 1.39 Hz, 1 H), 7.17 (s,l H), 3.59 (s, 2 H); MS ESI 211.0 (100) [M + H]+, calcd for [C13H10N2O + H]+ 211.2.

The synthetic route of 56341-37-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY HEALTH NETWORK; WO2009/79767; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem