Tag: M.W=200-300

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. 104618-32-8, name is 2-(4-Oxocyclohexyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Computed Properties of C14H13NO3

The title compound from Preparative Example 23 Step A (1.54 g, 8.23 mmol) was dissolved in ethanol (50 mL) and the title compound from Step C above (2 g, 8.23 mmol) was added. The mixture was stirred at room temperature for 1 h to become a suspension. The solvent was removed to afford the title compound as an off-white solid (3.3 g, quant.).1H-NMR (400 MHz, DMSO-d6): delta=2.00-2.18 (m, 3H), 2.27-2.43 (m, 2H), 2.50-2.63 (m, 2H), 3.30-3.38 (m, 1H), 4.46 (tt, 1H), 7.00 (d, 1H), 7.18 (d, 1H), 7.62 (t, 1H), 7.93-8.00 (m, 4H), 10.1 (s, 1H)

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

Related Products of 264916-06-5, 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. 264916-06-5, name is tert-Butyl 5-aminoisoindoline-2-carboxylate belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a cooled solution of 2.0 M of lithium tetrahydroborate in tetrahydrofuran (13 mL, 26 mmol) at 5C was added dropwise a solution of 5-amino-l,3-dihydro-isoindole-2- carboxylic acid tert-butyl ester (1.0 g, 4.3 mmol) in tetrahydrofuran (50 mL). Gas evolution was noted. The mixture was stirred for 1 hour at 5C then warmed to room temperature and stirred for 24 hours. The mixture was cooled to 5C in a ice/water bath and the reaction was quenched by addition of sodium sulfate decahydrate (3 g). Gas evolution noted. The mixture was stirred for 2 hours at room temperature. The suspension was filtered through a plug of diatomaceous earth and rinsed with with tetrahydrofuran. The filtrate was dried over magnesium sulfate, filtered and evaporated. The residue was purified via flash chromatography (silica gel column and 0%?20% methanol: dichloromethane). 2-Methyl-2,3-dihydro-lH-isoindol-5-ylamine was isolated as an orange solid (0.271 g, 43%). 1H NMR (400 MHz, (D3C)2SO, delta, ppm): 6.82 (d, J=I .9 Hz, IH), 6.41 (s, IH), 6.37 (d, J=8.1 Hz, IH), 4.86 (br s, 2H), 3.64 (s, 2H), 3.62 (s, 2H), 2.42 (s, 3H). MS = 149 (MH)+.

The synthetic route of tert-Butyl 5-aminoisoindoline-2-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CEPHALON, INC.; CURRY, Matthew A.; DORSEY, Bruce D.; DUGAN, Benjamin J.; GINGRICH, Diane E.; MESAROS, Eugen F.; MILKIEWICZ, Karen L.; WO2010/141796; (2010); A2;,
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Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 675109-26-9, name is 6-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 675109-26-9, Quality Control of 6-Bromoisoindolin-1-one

A mixture of 6-bromoisoindolin-i-one (5 g, 23.6 mmol), sodium azide (3.07 g, 47.2 mmol), sodium ascorbate (234 mg, 1.18 mmol), Cul (450 mg, 2.36 mmol) and trans-N,N-dimethyl- 1 ,2-diaminocyclohexane (504 mg, 3.54 mmol) in ethanol (35 mE) and water (15 mE) was stirred at reflux for 5.5 h under nitrogen. The reaction mixture was allowed to cool to room temperature and extracted with EtOAc (100 mEx3). The combined organic fractions were washed with brine and dried with anhydrous sodium sulfate.The solvent was evaporated under reduced pressure and the residue was purified by chromatography on silica gel (10- 50% EtOAc in pet. ether) to give iSA (1.2 g, 29% yield) as an off-white solid. ESI mlz 175.0 [M+i].

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Bromoisoindolin-1-one, and friends who are interested can also refer to it.

Reference:
Patent; Seal Rock Therapeutics, Inc.; BROWN, Samuel David; US2018/291002; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 2058-72-2, name is 5-Bromo-1-methylindoline-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 2058-72-2, Computed Properties of C9H6BrNO2

General procedure: To a stirring mixture of catalyst 1a (0.005 mmol) and cyclohexanone/acetone (5 mmol) in water (500 muL), additive DNP (0.920 mg, 0.005 mmol) was added at 25 C and the mixture was allowed to stir for 5 min followed by addition of isatin derivative (0.5 mmol). The mixture was stirred for 20-96 h and the progress of the reaction was monitored at regular intervals by TLC. On the completion of reaction, saturated solution of NH4Cl (5 mL) was added to it and resulting mixture was extracted with ethyl acetate (3×15 mL). The organic layer was separated, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to obtain crude aldol product. The column chromatography on silica gel (60-120 mesh) using hexane/ethyl acetate as an eluent gave the corresponding aldol adducts as a syn/anti mixture. The enantiomeric excess of aldol addition products was determined by chiral HPLC. The diastereoselectivity of product was determined by HPLC of crude reaction mixture. Racemic standards were prepared using (±) 3-methyl-1-morpholinobutan-2-amine catalyst synthesized form (±) valine.

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; Kumar, Akshay; Chimni, Swapandeep Singh; Tetrahedron; vol. 69; 25; (2013); p. 5197 – 5204;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, belongs to indolines-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Computed Properties of C9H4F3NO3

General procedure: The title compound was synthesized in one step from commercially available starting materials according to the following procedure. Into a 20mL microwave reaction vial, containing a magnetic stir bar, were weighed 5-(trifluoromethoxy)isatin (460mg, 2.0mmol), K2CO3 (550mg, 4.0mmol), KI (33mg, 0.20mmol), followed by acetonitrile (20mL, 0.1M) and 2-bromoethyl phenyl ether (480mg, 2.4mmol). After being sealed with a crimp cap, the vessel was placed in a microwave reactor and heated to 160C for 10min, with magnetic stirring. After cooling to ambient temperature, the reaction was diluted with CH2Cl2 (?20mL) and washed with brine. The organic layer was separated and dried over Na2SO4. Solvent was removed under reduced pressure and the crude product was purified via flash column chromatography (silica gel, hexane/ethyl acetate, 0-50% ethyl acetate gradient). Product containing fractions were combined and the solvents removed under reduced pressure to obtain 583mg of ML326 (83% yield) as a red-orange powder. TLC Rf=0.79 (hexane/ethyl acetate 1:1); 1H NMR (400MHz, CDCl3 calibrated to 7.26) delta 7.52-7.46 (m, 2H), 7.31-7.25 (m, 3H), 6.98 (t, J=7.4Hz, 1H), 6.82 (d, 2H), 4.28 (t, J=5.0Hz, 2H), 4.17 (t, J=5.0Hz, 2H); 13C NMR (125MHz, CDCl3 calibrated to 77.16) delta 182.25, 158.27, 157.93, 150.01, 145.44, 131.02, 129.78, 121.75, 118.32, 114.39, 112.89, 65.94, 40.62; HRMS calcd for C17H13NO4F3[M+H+]; 352.0797 found: 352.0795.

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

Reference:
Article; Gentry, Patrick R.; Bridges, Thomas M.; Lamsal, Atin; Vinson, Paige N.; Smith, Emery; Chase, Peter; Hodder, Peter S.; Engers, Julie L.; Niswender, Colleen M.; Scott Daniels; Jeffrey Conn; Wood, Michael R.; Lindsley, Craig W.; Bioorganic and Medicinal Chemistry Letters; vol. 23; 10; (2013); p. 2996 – 3000;,
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. 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. Product Details of 169037-23-4

Preparation of 3-hydroxy-5-trifluoromethoxy-3-(nitromethyl)indolin-2-one 5-trifluoromethoxy isatin ((0.115 g) and nitromethane (0.1 ml) were added to water and the reaction mixture was vigorously stirred at a temperature of 30 C. for 20 minutes. The obtained product was extracted with ethyl acetate and the solvent was removed to give pure product.

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

Reference:
Patent; RAO, Mandapati Mohan; PRATHIMA, Parvathaneni Sai; US2013/345438; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 6941-75-9, name is 5-Bromoisoindoline-1,3-dione, molecular formula is C8H4BrNO2, 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. COA of Formula: C8H4BrNO2

280 ml of 1M Borane-THF complex was added dropwise to a stirred solution of 4-bromophthalimide (20.85 g; 92.2 mmol) in anhydrous THF (200 ml) at 0 C. then heated at reflux overnight. The reaction was cooled to 0 C. then treated cautiously with methanol (100 ml) followed by 2M HCl (100 ml) then heated at reflux for 3 hours. The reaction mixture was cooled and the organics evaporated. The aqueous was diluted with water (100 ml) the extracted with DCM (×3). The aqueous was basified with 2M NaOH then extracted with DCM (×3). The combined DCM extracts were dried (MgSO4), filtered and evaporated to give 6.99 g of 5-bromo-2,3-dihydro-1H-isoindole as a dark brown gummy solid. 1H NMR (DMSO-d6) 7.45 (1H, s), 7.36 (1H, d), 7.20 (1H, d), 4.05 (4H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6941-75-9, its application will become more common.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; US2010/152184; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 667463-64-1, 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. 667463-64-1, name is 6-Bromo-1-methylindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Step 1: To a 250 mL flask equipped with a silicone oil bubbler was added commercially available isatin (7.7 g, 50 mmol) and anhydrous DMF (80 mL). the mixture was cooled down to 0 oC. To this solution was added NaH (1.32 g, 55 mmol), followed by the addition of CH3I in 15 min. Upon completion of the reaction (monitored by TLC), the mixture was diluted with saturated NH4Cl solution and extracted with ethyl acetate. The organic layer was washed with water, dried over Na2SO4, filtered, and concentrated to yield the crude N-methylindoline-2, 3-dione, which was used directly in the next step. Step 2: The N-methylindoline-2, 3-dione (7.58 g, 47 mmol) was refluxed in NH2·NH2-H2O ( 35 %) for 1h. Then the mixture was cooled to rt. The crude product was extracted with ethyl acetate. The combined organic layer was then dried over Na2SO4, purified by flash chromatography on silica gel (petroleum ether/ethyl acetate = 10:1). 1-Methylindolin-2-one was obtained as a pink solid.

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-Bromo-1-methylindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zhao, Jian-bo; Ren, Xinfeng; Zheng, Bu-quan; Ji, Jian; Qiu, Zi-bin; Li, Ya; Journal of Fluorine Chemistry; vol. 215; (2018); p. 44 – 51;,
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., category: indolines-derivatives

General procedure: A mixture of 6-chloro-5-(2-chloroethyl)-1,3-dihydro-2H-indol-2-one 1 (1.00mol), potassium carbonate (1.20mol), secondary amine (2a-h, 1.30mol) in water (10mL) was refluxed until completion (TLC, about 24-48h) and the reaction mass was cooled to RT and then extracted with DCM to get crude 3a-h. Recrystallized using aqueous acetone or aqueous ethanol or methanol (Yield 55-70%).

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; Meti, Gangadhar Y.; Kamble, Atulkumar A.; Kamble, Ravindra R.; Somagond, Shilpa M.; Devarajegowda; Kumari, Sandhya; Kalthur, Guruprasad; Adiga, Satish K.; European Journal of Medicinal Chemistry; vol. 121; (2016); p. 221 – 231;,
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. 193354-13-1, name is 5-Iodoindolin-2-one, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H6INO

5-Methoxycarbonyl-2-oxindole 5-Iodo-2-oxindole (17 g) was refluxed with 2 g of palladium diacetate, 18.2 g of triethylamine, 150 mL of methanol, 15 mL of dimethylsulfoxide and 2.6 g of DPPP in an atmosphere saturated with carbon monoxide. After 24 hours, the reaction was filtered to remove the catalyst and the filtrate concentrated. The concentrate was chromatographed on silica gel (30% ethyl acetate in hexane). The fractions containing product were concentrated and allowed to stand. The precipitated product was collected by vacuum filtration to give 0.8 g (7%) of the title compound as an off-white solid.

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; SUGEN, Inc.; US2003/69421; (2003); A1;; ; Patent; Sugen, Inc.; US6051593; (2000); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem