Category: 6872-06-6

Electric Literature of 6872-06-6, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 6872-06-6 name is 2-Methylindoline, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

2-methylindoline (3.26 g, 24.5 mmol) and hexane (0.536 M, 45.7 ml) were placed in a 100 ml Schlenk flask. N-BuLi (1.1 eq, 10.8 ml) was added at -20 & lt; 0 & gt; C and allowed to stand at room temperature overnight. Filtered through glass frit (G4) and vacuum dried to obtain phosphine-amine lithium. The phosphine-amine lithium (3.37 g, 24.2 mmol) was added to diethyl ether (0.423 M, 57.3 ml) in a 250 ml Schlenk flask and CO 2 bubbling was performed at -78 C for 1 hour. THF (1.1 eq, 2.16 ml) and t-BuLi (1.1 eq, 15.7 ml) were added at -20 C and kept at this temperature for 2 hours. IPr2PCl (0.85 eq, 3.14 g) and diethyl ether (0.359 M, 57.3 ml) were added at the same temperature and maintained at the same temperature for 1 hour. After slowly reacting at room temperature overnight, 50 ml of distilled water was added at 0 C, followed by stirring at room temperature for 30 minutes. Work-up with diethyl ether, drying over MgSO4, and then red oil was obtained in 2.23 g, 37% yield via hexane, diethyl ether 50: 1 column.

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; LG CHEM, LTD.; JANG, Jae Kwon; PARK, In Sung; KIM, Seul Ki; LEE, Eun Jung; LEE, Chong Hoon; HAN, Ki Won; HAN, Hyo Jung; (18 pag.)KR2017/68331; (2017); A;,
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

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

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

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

General procedure: The mixture of xylene (1.0 mL), substrate (0.3 mmol), and rGO (100 w%) was stirred at 100 C for 12 h under O2 atmosphere. After the reaction, the mixture was diluted with AcOEt and water. The organic phase was concentrated under reduced pressure, and purified by column chromatography with silica gel.

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

Reference:
Article; Morimoto, Naoki; Takeuchi, Yasuo; Nishina, Yuta; Chemistry Letters; vol. 45; 1; (2016); p. 21 – 23;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 6872-06-6, These common heterocyclic compound, 6872-06-6, name is 2-Methylindoline, 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.

2-methylindoline (3.26 g, 24.5 mmol) and hexane (0.536 M, 45.7 ml) were placed in a 100 ml Schlenk flask. At -20 C, n-BuLi (1.1 eq, 10.8 ml) was added and allowed to stand at room temperature overnight. Filtered through glass frit (G4) and vacuum dried to obtain phosphine-amine lithium. The phosphine-amine lithium (3.37 g, 24.2 mmol) was added to diethyl ether (0.423 M, 57.3 ml) in a 250 ml Schlenk flask and CO2 bubbling was added at -78 C for 1 hour. THF (1.1 eq, 2.16 ml) and t-BuLi (1.1 eq, 15.7 ml) were added at -20 C and kept at this temperature for 2 hours. IPr2PCl (0.85 eq, 3.14 g) and diethyl ether (0.359 M, 57.3 ml) were added at the same temperature and maintained at the same temperature for 1 hour. After slowly reacting at room temperature overnight, 50 ml of distilled water was added at 0 C, and the mixture was stirred at room temperature for 30 minutes. Work-up with diethyl ether, drying over MgSO4, and then red oil was obtained in 2.23 g, 37% yield via hexane, diethyl ether 50: 1 column

The synthetic route of 6872-06-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LG CHEM, LTD.; JANG, Jae Kwon; KIM, Seul Ki; PARK, In Sung; LEE, Eun Jung; LEE, Choong Hoon; HAN, Ki Won; HAN, Hyo Jung; (20 pag.)KR2017/68330; (2017); A;,
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. 6872-06-6, name is 2-Methylindoline, A new synthetic method of this compound is introduced below., Formula: C9H11N

Example 4Synthesis of 5-((2,3-dihydrobenzo[b][1,4]dioxin-6-yl)sulfonyl)-1-((4-fluorophenyl)sulfonyl)-2-methylindolineReagents MW Mole Reagent/raw material (g/mole) Quantity moles ratio 2-methylindoline 161.20 177 mg 1.33 mmol 1 eq. 4-fluorobenzene-1- 194.61 235 mg 1.33 mmol 1.0 eq. sulfonyl chloride 1-((4-fluorophenyl)sulfo- 291.34 267 mg 0.88 mmol 1.0 eq. nyl)-2-methylindoline 2,3-dihydro- 234.66 206 mg 0.88 mmol 1.0 eq. benzo[b][1,4]dioxine- 6-sulfonyl chloride Aluminium chloride 133.3 147 mg 1.1 mmol 1.25 eq. Step I: 2-methylindoline was dissolved in 5 mL dry pyridine, and 4-methoxybenzene-1-sulfonyl chloride was dropped in 2 portions under N2. The reaction was stirred for 2 hours at room temperature and an intense red color developed. When the reaction was complete as determined by HPLC using the protocol described above, as well as by TLC (8/2 PE/EtOAC), the crude reaction mixture was poured into 100 mL cold 0.5M HCl, and extracted twice with 50 mL CH2Cl2. The organic phase was evaporated, and the evaporation residue was purified by passing through a silica plug (100 g silica gel in large sinter glass). The product eluted in 7/3 PE/EtOAC, while all of the pink polar byproduct was retained on silica. The organic phase was dried on Na2SO4, and then evaporated and used for the next step without further purification (Product 100% pure, 378 mg, yield 99%).

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; Becker, Oren M.; Shitrit, Alina; Schutz, Nili; Ben-Zeev, Efrat; Yacovan, Avihai; Ozeri, Rachel; Kehat, Tzofit; Mirilashvili, Sima; Aizikovich, Alex; Sherman, Daniel; Behar, Vered; Kashtan, Osnat; US2012/108631; (2012); 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, name: 2-Methylindoline

General procedure: In a 2-neck RBF, 1 (20 mg, 0.0005 mmol) and TMNO (45 mg, 0.6 mmol) were suspended in toluene (4 mL) and to this solution indoline (60 mg, 0.5 mmol) was added. The reaction mixture was then heated to 100 oC for 20 h and it was filtered and solvent evaporated. The crude product obtained was purified by column chromatography using hexane/ethylacetate (7:1) as eluent to give pure indole (47 mg, 79%). A similar procedure was used for the other indolines and N-heterocycles.

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

Reference:
Article; Kumaran, Elumalai; Leong, Weng Kee; Tetrahedron Letters; vol. 59; 44; (2018); p. 3958 – 3960;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route 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.

Example 7Synthesis of 5-((2,3-dihydrobenzo[b][1,4]dioxin-6-yl)sulfonyl)-2-methyl-1-(phenylsulfonyl)indolineReagents MW Reagent/raw material (g/mole) Quantity moles 2-methylindoline 133.20 1 g 7.5 mmol benzenesulfonyl chloride 176.62 1.98 g 11 mmol 2-methyl-1- 273.35 0.76 g 2.77 mmol (phenylsulfonyl)indoline 2,3- 234.66 0.5 g 2.13 mmol dihydrobenzo[b][1,4]dioxine- 6-sulfonyl chloride Aluminium chloride 133.3 0.369 g 2.77 mmol Step 1: 2-methylindoline was dissolved in 5 mL dry pyridine, and benzenesulfonyl chloride was dropped in. The reaction was stirred for 2 hours at room temperature and an intense red color developed. When complete as determined by HPLC using the protocol in Example 1 above, as well as by LCMS, the crude reaction was poured into 100 mL cold 1M KHSO4, and extracted twice with 50 mL CH2Cl2. The organic phase was dried, evaporated and purified by CombiFlash to provide 2 grams of 100% pure product (97% 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:
Patent; Becker, Oren M.; Shitrit, Alina; Schutz, Nili; Ben-Zeev, Efrat; Yacovan, Avihai; Ozeri, Rachel; Kehat, Tzofit; Mirilashvili, Sima; Aizikovich, Alex; Sherman, Daniel; Behar, Vered; Kashtan, Osnat; US2012/108631; (2012); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 6872-06-6, name is 2-Methylindoline, 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. name: 2-Methylindoline

General procedure: Concentrated H2SO4(1.16 mmol in the case of amine 2a or 0.65 mmol in thecase of amines 2b,c,e,f) was added to a mixture of amine2a-,e,f (1.55 mmol) and 2 (20 ml). The mixture wasstirred at 60-70 until complete dissolution of amine.6-Chloropurine (1a) (200 mg, 1.29 mmol) was then added,and the obtained mixture was refluxed for 6 h, cooled, andtreated with aqueous ammonia to 8-9 with stirring. Theprecipitate that formed was filtered off and washed withcold water (3×3 ml). Compound 3a did not need furtherpurification, compounds 3b,c,e,f were purified by silica gelflash chromatography (eluent 95:5 CHCl3-MeOH).

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