Category: indolines-derivatives

Electric Literature of 114041-16-6, 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. 114041-16-6, name is 5,6-Dimethoxyisoindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Compound 427:Dichloropyrimidine (298 mg, 2.0 mmol) was dissolved in dry THF (10 ml_) with Et3N (280 uL, 2.0 mmol). The mixture was cooled to 0 C, and isoindoline (380 mg, 2.1 mmol) was added. The resulting mixture was warmed to room temperature and stirred for 3 hours. The EtOAc was added to dilute the mixture and the organics was washed with water, brine and dried over Na2SO4. After concentration, the residue was purified with column (silica gel, EtOAc/Hexane = 30:70) to give the product 427 (311 mg) as light yellow solid. HPLC-MS tR = 1.49 min (UV254 nm); mass calculated for formula C14H14CIN3O2 291.1 , observed LCMS m/z 292.1 (M+H).

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

Reference:
Patent; SCHERING CORPORATION; WO2009/14637; (2009); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 24566-79-8, 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. 24566-79-8, name is N-(6-Bromohexyl)phthalimide belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a stirred solution of 2-5 (5 mmol) in THF (60 mL) was added potassium thioacetate (15 mmol), and the mixture was refluxed for 3-4 h. And the solvent was evaporated to dryness in vacuo, and then added water (30 mL), and the organic materials were extracted with EtOAc (3×30 mL). The combined extracts were washed with water and brine, dried over anhydrous MgSO4, and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel (EtOAc:petroleum ether=1:8) to give compounds 6-9 as white powder.

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, N-(6-Bromohexyl)phthalimide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Hu, Kun; Qi, Yan-Jie; Zhao, Juan; Jiang, He-Fei; Chen, Xin; Ren, Jie; European Journal of Medicinal Chemistry; vol. 64; (2013); p. 529 – 539;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 1127-59-9, 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. 1127-59-9, name is 7-Methylindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

Step 3: 5-bromo-7-methylindoline-2,3-dioneTo a stirred mixture of 7-methylindoline-2,3-dione (7 g, 0.043 mol) in chloroform (700 mL) was added a solution of bromine (2.8 mL, 0.053 mol) in chloroform (100 mL) dropwise over 15 min at room temperature. The reaction mixture was heated at 80°C for 24 h and then cooled to 0°C, which resulted in precipitation of the product as a red solid. The solid was collected by suction filtration and dried under vacuum to afford the title compound (8 g, 77percent).XH NMR (400 MHz, DMSO-d6) : delta 11.20 (s, 1H), 7.64 (d, J = 1.2 Hz, 1H), 7.42 (d, J = 7.2 Hz, 1H), 2.18 (s, 3H); ESI-MS: Calculated mass: 238.96; Observed mass: 238.30 [M-H]”.

The chemical industry reduces the impact on the environment during synthesis 7-Methylindoline-2,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ASANA BIOSCIENCES, LLC; THOMPSON, Scott, K.; SMITH, Roger, A.; REDDY, Sanjeeva; JOHN, Tyler, M.; NYAVANANDI, Vijay, Kumar; SUBRAMANYA, Hosahalli; POTLURI, Vijay; PANIGRAHI, Sunil, Kumar; NADIPALLI, Prabhakara, Rao; SENGUPTA, Saumitra; WO2014/169167; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 6872-06-6, name is 2-Methylindoline, 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 6872-06-6, Recommanded Product: 2-Methylindoline

To a solution of 2-methylindoline (21 muL, 0.16 mmol) in dichloroethane (1 mL) was added Na(OAc)3BH (88 mg, 0.415 mmol). The mixture was stirred at room temperature under argon for 20 min. A slurry of 3-(4-formyl-phenyl)-isoxazole-5-carboxylic acid amide (which may be prepared as described in Preparation of Intermediate 20; 20 mg, 0.093 mmol) in dichloroethane (1 mL) was added, followed by AcOH (20 muL). The reaction mixture was stirred at room temperature overnight. 1 M Na2CO3 solution was added and the mixture was extracted with CHCl3 (3 x 25 mL). The organic layer was washed with brine, dried (Na2SO4), evaporated, and purified by chromatography (11-20% acetone/CH2Cl2) to give 3-[4-(2-methyl-2,3-dihydro-indol-1-ylmethyl)-phenyl]-isoxazole- 5-carboxylic acid amide (25 mg, 54%) as a white powder. 1H NMR (300 MHz, DMSO-d6) delta ppm 8.36 (br. s., 1 H), 7.98 (br. s., 1 H), 7.85 (d, J=8.2 Hz, 2 H), 7.56 (s, 1 H), 7.48 (d, J=7.8 Hz, 2 H), 6.99 (d, J=7.2 Hz, 1 H), 6.84 – 6.94 (m, 1 H), 6.53 (t, J=7.4 Hz, 1 H), 6.31 (d, J=7.8 Hz, 1 H), 4.45 (d, J=16.3 Hz, 1 H), 4.14 – 4.27 (m, 1 H), 3.57 – 3.76 (m, 1 H), 3.12 (dd, J=15.8, 8.6 Hz, 1 H), 2.56 (dd, J=16.0, 9.4 Hz, 1 H), 1.25 (d, J=6.3 Hz, 3 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Methylindoline, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; ERICKSON, Shawn, David; GILLESPIE, Paul; MERTZ, Eric; WO2014/86704; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 6872-06-6, A common heterocyclic compound, 6872-06-6, name is 2-Methylindoline, molecular formula is C9H11N, 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: 2-Methylindoline (400 mg, 3.0 mmol, 1.0 equiv) was dissolved in dry pyridine (10 mL). Methane sulfonyl chloride (480 mg, 4.2 mmol, 1.4 equiv) was added dropwise and the reaction mixture was stirred overnight at rt. Monitoring by HPLC and LCMS indicated that the reaction was completed. The solvent was evaporated under reduced pressure. A solution of HCl 1N (50 mL) and EtOAc (50 mL) were added. The organic layer was separated and the aqueous phase was extracted twice with EtOAc (2×50 mL). The combined organic phase was dried over Na2SO4 and the solvent was evaporated under reduced pressure to yield the pure product: 634 mg, 100 % yield.

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; Yacovan, Avihai; Ozeri, Rachel; Kehat, Tzofit; Mirilashvili, Sima; Sherman, Daniel; Aizikovich, Alex; Shitrit, Alina; Ben-Zeev, Efrat; Schutz, Nili; Bohana-Kashtan, Osnat; Konson, Alexander; Behar, Vered; Becker, Oren M.; Bioorganic and Medicinal Chemistry Letters; vol. 22; 20; (2012); p. 6460 – 6468;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 6872-06-6, 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. 6872-06-6, name is 2-Methylindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: N-heterocycle substrate (0.2 mmol), Na-AMO (20 mg, 10 mol%), catechol Q-2 (3.3 mg, 0.02 mmol) was added into a reaction tube. The reaction tube was filled and protected with oxygen using a O2 balloon, then H2O was added into the reaction tube with a syringe. The reaction was allowed to react at room temperature for 20 h. After completion of reaction, the resulting mixture was filtered, washed with EtOAc and extracted by EtOAc. The organic phases were combined, washed with brine and dried with Na2SO4. Next, organic solution was concentrated under reduced vacuum to give the crude product. Finally, the product was purified by silica gel chromatography to yield the pure product.

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

Reference:
Article; Tang, Tao; Bi, Xiuru; Meng, Xu; Chen, Gexin; Gou, Mingxia; Liu, Xiang; Zhao, Peiqing; Tetrahedron Letters; vol. 61; 5; (2020);,
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. 17564-64-6, name is 2-(Chloromethyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C9H6ClNO2

EXAMPLE 1 N-(3,5-di-tert-butyl-4-hydroxyphenylthiomethyl)phthalimide A vessel was charged with 12.19 grams of 3,5-di-tert-butyl-4-hydroxybenzene thiol and 3.30 grams of potassium hydroxide dissolved in 50 ml of acetone and 2 ml of water at 0 C. which was mixed with 10.0 grams of N-(chloromethyl)phthalimide. After stirring for one hour, the precipitated product was removed by filtration and then recrystallized from ethyl acetate-hexane to give 14.9 grams of produt, m.p. 151-53 C. Anal. Calc’d for C23 H27 NO3 S: C, 69.5; H, 6.9; N, 3.5. Found: C, 69.5, H, 7.0, N, 3.6.

According to the analysis of related databases, 17564-64-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ciba-Geigy Corporation; US4692532; (1987); A;,
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. 40314-06-5, name is 5-Methylisoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C9H7NO2

Isovaleryl chloride (0.50 mL, 4.1 mmol) was added to a mixture of 4-methylphthalimide (0.78 g, 4.8 mmol), triethylamine (0.86 mL, 6.2 mmol), and acetonitrile (8.2 mL) at room temperature and with stirring. After 24 h, the mixture was diluted in EtOAc and washed with satd aq NaHCO3 and brine. The organic phase was dried (MgSO4) and concentrated. The crude material was purified by flash chromatography (SiO2, hexanes:EtOAc 4:1) to give 10 (713 mg, 2.91 mmol, 71%) as a white solid. 1H NMR (300 MHz, CDCl3): delta 7.83 (d, J=7.7Hz, 1H), 7.74 (s, 1H), 7.65 (d, J=7.6Hz, 1H), 2.90 (d, J=6.9Hz, 2H), 2.57 (s, 3H), 2.25 (septet, J=6.7Hz, 1H), and 1.03 (d, J=6.7Hz, 6H). 13C NMR (75 MHz, CDCl3): delta 171.6, 165.6, 165.5, 147.1, 136.2, 131.4, 128.5, 124.6, 124.3, 47.4, 25.0, 22.4, and 22.1. IR (neat): 2956, 1750, 1711, 1612, 1364, 1309, 1109, 1047, and 738 cm-1. HRMS: Calcd for C14H15NNaO3+ [M+Na+] requires 268.0944; found 268.0945. Mp: 180-186 C.

According to the analysis of related databases, 40314-06-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Enright, Robert N.; Grinde, Jeffrey L.; Wurtz, Lincoln I.; Paeth, Matthew S.; Wittman, Tekoa R.; Cliff, Emily R.; Sankari, Yessra T.; Henningsen, Lucas T.; Tan, Chuchen; Scanlon, Joseph D.; Willoughby, Patrick H.; Tetrahedron; vol. 72; 41; (2016); p. 6397 – 6408;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 99365-40-9,Some common heterocyclic compound, 99365-40-9, name is 6-Bromoindolin-2-one, molecular formula is C8H6BrNO, 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) 6-Bromo-3,3-dimethyl-l,3-dihydro-indol-2-one To a suspension of potassium tert-butylate (12.8 g, 114 mmol) in dry THF (80 ml) at 0C under an argon atmosphere was added portionwise 6-bromoindolin-2-one (5.0 g, 22.9 mmol) followed by copper(I) bromide-dimethylsulfide complex (470 mg, 2.29 mmol). Mel (6.82 g, 3.00 ml, 48.0 mmol) was added dropwise within 45 minutes, keeping temperature of the reaction mixture below 8C. The reaction mixture was warmed to room temperature and kept at this temperature for 16 hours. The reaction mixture was cooled to 0C again and saturated aqueous ammonium chloride solution was cautiously added. The mixture was diluted with tert-butyl methyl ether and water. The aqueous phase was extracted with tert-butyl methyl ether, the combined organic phases were dried over sodium sulfate, the solvent was evaporated and the residue purified by silica gel chromatography using ethyl acetate/ heptane as eluent. The title compound was obtained as light yellow solid (5.17 g). MS ESI (m/z): 240.0/ 242.1 [(M+H)+]. 1H NMR (CDC13, 400 MHz): (ppm) = 8.12 (m, 1H), 7.20-7.16 (m, 1H), 7.09-7.08 (m, 1H), 7.06-7.04 (m, 1H), 1.39 (s, 6H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Bromoindolin-2-one, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BRUNNER, Daniela; MALBERG, Jessica; SHANKAR, Bavani G.; KOLCZEWSKI, Sabine; LIMBERG, Anja; PRINSSEN, Eric; RIEMER, Claus; STOLL, Theodor; WO2014/40969; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 6326-79-0, name is 6-Bromoisatin, 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 6326-79-0, Application In Synthesis of 6-Bromoisatin

To R27 (25.0 g, 111 mmol) in acetonitrile (750 mL) is added MeI (15 mL, 241 mmol) and K2CO3 (60.0 g, 434 mmol) and the reaction mixture is stirred at 60 C. for 2 h. The reaction mixture is filtered and concentrated. Water and ethyl acetate are added to the residue. The organic layer is extracted twice with water, dried over MgSO4 and concentrated. Yield 56%, m/z 240/242 [M+H]+, rt 0.48 min, LC-MS Method X001-004.

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

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ANDERSKEWITZ, Ralf; BINDER, Florian; GRAUERT, Matthias; GRUNDL, Marc; HAEBEL, Peter Wilhelm; OOST, Thorsten; PAUTSCH, Alexander; PETERS, Stefan; VINTONYAK, Viktor; US2014/275025; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem