Author: Jessica.F

Related Products of 7699-18-5,Some common heterocyclic compound, 7699-18-5, name is 5-Methoxyindolin-2-one, molecular formula is C9H9NO2, 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: To a solution of 2-oxindole (3.76mmol) in dry THF (8 mL) was added BuLi (1.63 M, 7.52 mmol) at -78 C followedby N,N,N,N-tetramethylethylenediamine (7.52 mmol). After stirring themixture for 1 h at the same temperature, 4-(2-iodoethyl)-N,N-dimethylaniline(4.51 mmol) dissolved in THF (8 mL) was added dropwise to thesolution. Then, the solution was allowed to warm to ambient temperature, andthe stirring was continued for further 2 h. The reaction mixture was pouredinto saturated ammonium chloride solution and the product was extracted withethyl acetate. The organic layer was dried over anhydrous sodium sulfate,filtered, and concentrated under reduced pressure. The residual was purified bysilica gel column chromatography (hexane/ethyl acetate/acetone = 5/1/1) toafford 2 (74%) as a pale pink solid.

The synthetic route of 7699-18-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Furuta, Kyoji; Kawai, Yu; Mizuno, Yosuke; Hattori, Yurika; Koyama, Hiroko; Hirata, Yoko; Bioorganic and Medicinal Chemistry Letters; vol. 27; 18; (2017); p. 4457 – 4461;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 6941-75-9, 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. 6941-75-9 name is 5-Bromoisoindoline-1,3-dione, 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.

A mixture of 5-bromoisoindoline-1,3-dione (2.5 g, 11.06 mmol) and Pd(Ph3P)4 (1.406 g, 1.217 mmol) in DMF (50 ml) was accurately degassed with nitrogen, then Zn(CN)2 (1.299 g, 11.06 mmol) was added, and the solution, splitted in 5 vials, was heated under microwave irradiation at 200 C. for 1 hour. A 3% aqueous solution of NH4OH (200 ml) was added, and the organic phase was extracted with ethyl acetate (3¡Á150 ml). The combined organic layers were washed with brine (150 ml), dried over sodium sulfate and concentrated to dryness. The crude was purified by silica gel flash chromatography (100% DCM to DCM_MeOH=99:1) to afford 1,3-dioxoisoindoline-5-carbonitrile as (0.522 g, 3.03 mmol, 27.4% yield, MS/ESI+ 172.9 [MH]+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromoisoindoline-1,3-dione, and friends who are interested can also refer to it.

Reference:
Patent; Chiesi Farmaceutici S.p.A.; ARMANI, Elisabetta; Amari, Gabriele; Capaldi, Carmelida; Carzaniga, Laura; La Porta, Elena; Guala, Matilde; US2013/102576; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 39603-24-2, 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. 39603-24-2, name is 5,7-Dimethylindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: The mixture of isatin 1 (29.4 mg, 0.2 mmol), antipyrine 2a (84.7 mg, 0.45 mmol) in 1mL H2O were stirred at 120 . Once the reaction completed (indicated by colorchange from red to white), the mixture was then cooled down to the room temperature.The insoluable solid mixture was filtered, washed by water and dried under vacuum to afford the desired product 4a in high pure form.

The chemical industry reduces the impact on the environment during synthesis 5,7-Dimethylindoline-2,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Article; Zhang, Yong; Nie, Long-Jun; Luo, Liang; Mao, Jia-Xin; Liu, Jin-Xiang; Xu, Guo-Hai; Chen, Deliang; Luo, Hai-Qing; Tetrahedron; vol. 76; 7; (2020);,
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. 885272-46-8, name is tert-Butyl 4-bromoindoline-1-carboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: 885272-46-8

To a solution tert-butyl 4-bromoindoline-1-carboxylate (1.0 g, 3.354 mmol) and benzophenone hydrazone (0.658 g, 3.354 mmol) in 1,4-dioxane (15 mL) at room temperature under nitrogen, BINAP (209 mg, 0.335 mmol), palladium (II) acetate (75 mg, 0.335 mmol) and sodium t-butoxide (967 mg, 10.061 mmol) were added and the mixture was heated at 100 C. for 16 h. The resultant mixture was cooled to room temperature, filtered and the filtrate concentrated under reduced pressure to give the crude product, which was purified by flash chromatography (SiO2, heptane-ethyl acetate gradient). Pure fractions were combined and concentrated. The resultant solids were dried under reduce pressure to afford tert-butyl 4-(2-(diphenylmethylene)hydrazinyl)indoline-1-carboxylate, cpd 130a (912 mg, 65.8% yield). MS m/z 414.1 (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:
Patent; Janssen Pharmaceutica NV; Lu, Tianbao; Connolly, Peter J.; Cummings, Maxwell David; Barbay, Joseph Kent; Kreutter, Kevin D.; Wu, Tongfei; Diels, Gaston Stanislas Marcella; Thuring, Jan Willem; Philippar, Ulrike; Edwards, James Patrick; Shen, Fang; (202 pag.)US2019/381019; (2019); A1;,
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. 3339-73-9, name is 3-(1,3-Dioxoisoindolin-2-yl)propanoic acid, A new synthetic method of this compound is introduced below., SDS of cas: 3339-73-9

240 g (1.09 mol) of phthalic anhydride alanine was added to a 1000 mL reaction flask.700 mL of chloroform, warmed to 60 C, and 135 g (1.13 mol) of thionyl chloride was added dropwise.After the completion of the dropwise addition, the reaction was kept for 3 hours, and concentrated under reduced pressure to dryness.Add 400 mL of chloroform to dissolve and set aside.

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; Hubei Hongtai Biological Technology Co., Ltd.; Zhang Rui; Lei Yuping; Wang Liming; Wu Weiwei; Li Jianxiong; (8 pag.)CN109053580; (2018); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 199328-10-4, The chemical industry reduces the impact on the environment during synthesis 199328-10-4, name is Methyl Oxindole-5-carboxylate, I believe this compound will play a more active role in future production and life.

EXAMPLE I Methyl 1-acetyl-2-indolinone-5-carboxylate 10.5 g of methyl 2-indolinone-5-carboxylate (prepared analogously to Ogawa et al. Chem. Pharm. Bull 36, 2253-2258 (1988)) are stirred in 30 ml of acetic anhydride for 4 hours at 140 C. Then it is allowed to cool, poured onto ice water and the precipitate is suction filtered. The product is again washed with water, then taken up in methylere chloride, dried over sodium sulphate and concentrated by evaporation. Yield: 11 g (86% of theory), Rf value: 0.63 (silica gel; methylene chloride/methanol=50:1)

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, Methyl Oxindole-5-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Boehringer Ingelheim Pharma KG; US6169106; (2001); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 3485-84-5,Some common heterocyclic compound, 3485-84-5, name is N-Vinylphthalimide, molecular formula is C10H7NO2, 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.

To a solution of N-vinyl-phthalimide (618 mg, 3.57 mmol) and bis[rhodium(alpha, alpha, alpha?,alpha?-tetramethyl-1,3-benzenedipropionic acid)] (5.90 mg, 0.00778mmol) in anhydrous CH2Cl2 (8 mL) was added a solution of diazomalonate S3 (1.43 g,3.92 mmol) (preparation method was shown below) in anhydrous CH2Cl2 (8 mL)dropwise at 0 C under an Ar atmosphere. The reaction was allowed to warm to 23 Cand stirred for 20 h at 23 C. The solvent was then removed in vacuo and the crudematerial was purified by recrystallization (ethyl acetate) to give 5g (666 mg, 1.30mmol) in 33% yield as a white solid.

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

Reference:
Article; Kaga, Atsushi; Gandamana, Dhika Aditya; Tamura, Sayako; Demirelli, Mesut; Chiba, Shunsuke; Synlett; vol. 28; 9; (2017); p. 1091 – 1095;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 15861-23-1, A common heterocyclic compound, 15861-23-1, name is Indoline-5-carbonitrile, molecular formula is C9H8N2, 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.

To a suspension of NaH (2.5 g, 108 mmol) in DMF (100 mL) at 0 C. was added 2,3-dihydro-1H-indole-5-carbonitrile (6.2 g, 43.0 mmol). After 15 min, CS2 (3.8 mL, 64.6 mmol) was added followed by MeI (4.0 mL, 64.6 mmol). The reaction mixture was stirred for 1 h at room temperature. The reaction mixture was then was poured onto ice. The resulting mixture was filtered. The remanence was washed with methylene chloride to give 5-cyano-2,3-dihydroindole-1-carbodithioic acid methyl ester as a off-white solid (7.5 g, 76%). The material was used without further purification.

The synthetic route of 15861-23-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; H. Lundbeck A/S; US2012/252853; (2012); A1;,
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. 65826-95-1, name is 5-Methylindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 65826-95-1

A solution of an HCl salt of Intermediate JB-6 (280 mg, 0.803 mmol) in DCM (2 mL) was added dropwise at 0 C to a stirred solution of sulfurisocyanatidic chloride (0.010 mL, 1.1 mmol) in DCM (3 mL). The reaction mixture was stirred at 0 C for lh and then TEA (0.358 mL, 2.57 mmol) in DCM (1.1 mL) was added and reaction mixture was stirred at 0 C for 3 min. A portion of the crude reaction mixture (-0.8 mL) was added to a stirred solution of 5-methylindoline (32.1 mg, 0.241 mmol) in DCM (1 mL) and the reaction was stirred at rt for 2 h. The reaction mixture was concentrated and partitioned between EtOAc (~2 mL) and 1M HCl (~1 mL) (note: for reactions that followed the procedure outlined here, where there was a basic amine present in the final Example, sat. aq NaHCC was used in the work-up in place of 1 M HC1) and the organic component was washed with brine (1 mL) and concentrated. The residue was dissolved into MeOH, filtered and purified by preparative HPLC to yield the title compound (5.6 mg). LC-MS retention time = 2.88 min; m/z = 551.5 [M+H]+. (Column: Waters BEH C18, 2.0 x 50 mm, 1.7-muiotaeta particles. Solvent A = 95% Water : 5% MeOH : 10 mM NH4OAc. Solvent B = 5% Water : 95% MeOH : 10 mM NH4OAc. Flow Rate = 0.5 mL/min. Start % B = 0. Final % B = 100. Gradient Time = 3 minutes, then a 0.5-minute hold at 100% B. Wavelength = 220). 1H NMR (500 MHz, DMSO-d6) delta 7.24 – 7.04 (m, 4H), 7.00 – 6.66 (m, 8H), 6.21 (br. s., IH), 4.18 (app q, J=7.1 Hz, IH), 4.04 (q, J=7.1 Hz, 2H), 3.94 – 3.82 (m, 2H), 3.58 (d, J=7.0 Hz, IH), 3.49 – 3.39 (m, IH), 2.94 – 2.84 (m, 2H), 2.68 (br. s., IH), 2.47 (dd, J=13.2, 7.3 Hz, IH), 2.21 (s, 3H), 1.35 (t, J=6.8 Hz, 3H), 0.93 (t, J=7.0 Hz, 3H).

The synthetic route of 65826-95-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BENDER, John A.; GENTLES, Robert G.; PENDRI, Annapurna; WANG, Alan Xiangdong; MEANWELL, Nicholas A.; BENO, Brett R.; FRIDELL, Robert A.; BELEMA, Makonen; NGUYEN, Van N.; YANG, Zhong; WANG, Gan; KUMARAVEL, Selvakumar; THANGATHIRUPATHY, Srinivasan; BORA, Rajesh Onkardas; HOLEHATTI, Shilpa Maheshwarappa; METTU, Mallikarjuna Rao; PANDA, Manoranjan; (319 pag.)WO2016/172424; (2016); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 114041-16-6, These common heterocyclic compound, 114041-16-6, name is 5,6-Dimethoxyisoindoline, 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 67 2-[7-(3,4-Dimethoxyphenyl)-7-[(4-methylphenyl)thio]-heptyl]-1,2,3,4-tetrahydro-6,7,8-trimethoxyisoquinoline The procedure of Example 49 is repeated using 5.31 g 4-[6-bromo-1-[(4-methylphenyl)thio]heptyl]-1,2-dimethoxybenzene, 3.29 g of 5,6-dimethoxyisoindoline and 2.65 g of 6,7,8-trimethoxy-1,2,3,4-tetrahydroisoquinoline. This affords 4.52 g of the desired product as a yellow oil.

The synthetic route of 114041-16-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Powell; Dennis; Paul; Rolf; Hallett; William A.; Berger; Dan M.; Dutia; Minu D.; US5387685; (1995); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem