Category: indolines-derivatives

These common heterocyclic compound, 7699-18-5, name is 5-Methoxyindolin-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. Quality Control of 5-Methoxyindolin-2-one

General procedure: To a Schlenk tube were added indolin-2-one 1 (0.3 mmol), t-BuOOH (0.6 mmol), and DCE (2 mL). Then the tube was stirred at 85 oC under air for the indicated time until complete consumption of starting material monitored by TLC analysis. After the reaction was finished, the reaction mixture was washed with brine. The aqueous phase was re-extracted with ethyl acetate (3¡Á10 mL). The combined organic extracts were dried over Na2SO4, removal of the solvent under vacuum afforded the crude product, which was purified further by column chromatography using hexane-ethyl acetate (10:1).

The synthetic route of 5-Methoxyindolin-2-one has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ying, Wei-Wei; Zhu, Wen-Ming; Liang, Hongze; Wei, Wen-Ting; Synlett; vol. 29; 2; (2018); p. 215 – 218;,
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17702-83-9, name is 2-(8-Bromooctyl)isoindoline-1,3-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. name: 2-(8-Bromooctyl)isoindoline-1,3-dione

General procedure: To a solution of compound 4 (2 mmol) in N,N-dimethylformamide (DMF) (40.0 mL), the intermediate 2 (0.44 g, 2.5 mmol) and KHCO3 (0.40 g, 4.0 mmol) were added. The mixture was heated at 35-40C for 10 h. Monitored by TLC, and then filtered, concentrated by vacuum. The crude compound was purified by column chromatography on silica gel (VEtOAc-VPet = 2 : 3) to give compound 5. (Chart 1). The 1H-NMR data of compounds 5a-i were listed as follow.

The synthetic route of 17702-83-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Xie, Ruliang; Mei, Xiangdong; Ning, Jun; Chemical and Pharmaceutical Bulletin; vol. 67; 4; (2019); p. 345 – 350;,
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Related Products of 3676-85-5,Some common heterocyclic compound, 3676-85-5, name is 5-Aminoisoindoline-1,3-dione, molecular formula is C8H6N2O2, 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.

Preparative Example 1 4-Cyanophthalimide STR16 4-Aminophthalimide (40.0 g) was suspended in 300 ml of water, followed by the addition of 57 ml of concentrated hydrochloric acid. The obtained suspension was stirred under cooling with ice. A solution of 20.6 g of sodium nitrite in 69 ml of water was dropped into the above suspension at a bulk temperature of 5 C. or below. The obtained mixture was cooled to -20 C., followed by the addition of 300 ml of toluene. The resulting mixture was adjusted to pH7 with sodium hydrogencarbonate under vigorous stirring to form a diazonium salt. Separately, a solution of 105.7 g of potassium cyanide in 206 ml of water was dropped into a suspension of 63.4 g of cuprous chloride in 250 ml of water, while the suspension was vigorously stirred under cooling with ice. The obtained mixture was further stirred under cooling with ice for one hour, followed by the addition of 500 ml of ethyl acetate. The diazonium salt prepared above was added into the resulting mixture in several portions and the obtained mixture was stirred under cooling with ice for one hour. The resulting mixture was filtered through Celite to remove insolubles and the Celite was washed with an ethyl acetate/tetrahydrofuran mixture. The filtrates were together left standing to cause liquid-liquid separation. The organic phase was washed with a saturated aqueous solution of sodium hydrogen-carbonate, dilute hydrochloric acid and a saturated aqueous solution of common salt, dried over anhydrous magnesium sulfate and freed from the solvent by vacuum distillation. The title compound (41 g) was obtained as a reddish-brown solid. M.p.: 237.0-238.0 C.; MASS: 173 (MH+); 1H–NMR (400 MHz, DMSO-d6) delta: 8.00(1H, dd, J=7.5, 1.0 Hz), 8.29(1H, dd, J=7.5, 1.5 Hz), 8.36(1H, dd, J=1.5, 1.0 Hz), 11.73(1H, s)

The synthetic route of 3676-85-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Eisai Co., Ltd.; US5849741; (1998); A;,
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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. 107583-37-9, name is 5,6,7-Trifluoroindoline-2,3-dione, A new synthetic method of this compound is introduced below., Application In Synthesis of 5,6,7-Trifluoroindoline-2,3-dione

EXAMPLE 6 5,7-difluoro-6-(4-methylpiperazinyl)isatin STR14 Using the procedure in Example 4 and substituting 5,6,7-trifluoroisatin for 5,6-difluoroisatin gave the title compound in 70% 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; PathoGenesis Corporation; US5441955; (1995); A;,
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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;,
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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;,
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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;,
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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;,
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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;,
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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;,
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