Category: indolines-derivatives

These common heterocyclic compound, 2058-74-4, name is 1-Methylisatin, 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. Recommanded Product: 1-Methylisatin

A solution of N-methylisatin (161 mg, 1.0 mmol), indole (129 mg, 1.1 mmol), and K2CO3 (69 mg, 0.5 mmol) in aqueous DMF (H2O/DMF, 2:1, 3.0 mL) was heated to 50 oC for 3 h. After aqueous extractive workup and column chromatographic purification process (n-hexane/EtOAc, 1:1), 1a was obtained as a white solid, 170 mg (61%).1,2 Other compounds were synthesized similarly, and compounds 1a1,2 and 1l3,7 are known compounds. Compound1a?1,4 was prepared according to the reported method.16 The spectroscopic data of unknown compounds 1b-d are as follows.

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

Reference:
Note; Seo, Da Young; Roh, Hwa Jung; Min, Beom Kyu; Kim, Jae Nyoung; Bulletin of the Korean Chemical Society; vol. 38; 12; (2017); p. 1519 – 1522;,
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2518-24-3, name is 4-Aminoisoindoline-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. Recommanded Product: 2518-24-3

(1) The solid phthalic anhydride and urea are added to the reactor and heated to 136 C for 320 seconds. The prepared o-aminobenzene dicarboximide is introduced into the first tubular reactor together with water and sodium hydroxide and forced cooled to -15 deg. C; The Hoffmann degradation reaction was carried out by adding methanol and sodium nitrite solution at 1: 0.5, the reaction time was 48 seconds, and then separating the o-aminobenzoic acid methyl ester;

The synthetic route of 2518-24-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tian, Zixin; Tian, Zhenmin; Yang, Yuanxi; Wang, Jilong; Cui, Zhen; (6 pag.)CN105949091; (2016); A;,
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Related Products of 350797-56-7, 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. 350797-56-7, name is 3-(7-Cyano-5-(2-nitropropyl)indolin-1-yl)propyl benzoate, This compound has unique chemical properties. The synthetic route is as follows.

To the solution of 394g of 3-(7-cyano-5-(2-nitropropyl)indolin-l-yl)propyl benzoate in 2000ml of methanol and 800ml of ethyl acetate was added 39.4g of palladium hydroxide in an autoclave. Heated the reaction mass under hydrogen pressure of lOkg/cm3 at 50-55C till completion of reaction. Filtered the catalyst and concentrated the filtrate to get 346g of desired amino compound.

The chemical industry reduces the impact on the environment during synthesis 3-(7-Cyano-5-(2-nitropropyl)indolin-1-yl)propyl benzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; MANKIND RESEARCH CENTRE; SINGH, Gurpreet; GANGWAR, Kuldeep Singh; BHASHKAR, Bhuwan; KUMAR, Anil; WO2014/167507; (2014); A1;,
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These common heterocyclic compound, 99365-40-9, name is 6-Bromoindolin-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. HPLC of Formula: C8H6BrNO

bl .l) 2-Oxoindoline-6-carbonitrile A mixture of palladium-tetrakis(triphenylphosphine) (10.90 g, 9.43 mmol), 6- bromoindolin-2-one (10 g, 47.2 mmol) and dicyanozinc (7.75 g, 66.0 mmol) in DMF (80 mL) was heated to 80 C for 16 h. The reaction mixture was cooled to rt and water was added. The aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2S04, filtered, and concentrated under reduced pressure. The crude material was purified by column chromatography (silica gel column and elution with 5% MeOH/CfLC^) to give 2-oxoindoline-6-carbonitrile (5.97 g, 37.7 mmol, 80 % yield) as a brown solid. RT=1.15 min (3 min).

The synthetic route of 6-Bromoindolin-2-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBVIE DEUTSCHLAND GMBH & CO. KG; GENESTE, Herve; HORNBERGER, Wilfried; JANTOS, Katja; KLING, Andreas; VAN GAALEN, Marcel; (122 pag.)WO2015/173393; (2015); A1;,
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Related Products of 99365-40-9, 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. 99365-40-9, name is 6-Bromoindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 6-bromo-2-oxindole (1 equiv) in NMP (0.05 M) were added bispinacolato diboron (2.4 equiv), potassium acetate (1.5 equiv), dppf (0.05 equiv) and PdCl2(dppf) (0.05 equiv). The reaction mixture was stirred at 130C for 3 hours and then concentrated in vacuo. The residue was partitioned between water and ethyl acetate. The organic phase was dried over anhydrous sodium sulphate, filtered and concentrated in vacuo. The crude residue was purified by flash column chromatography on silica gel eluting with EtOAc/hexane (9 / 1), yielding the desired product as a red solid. 6-(4,4,5,5-Tetramethyl-[l,3,2]dioxaborolan-2-yl)-l,3-dihydro-indol-2-one: (22 % yield, 51 % purity main impurity being the boronic acid 28 %) m/z (LC-MS, ESP): 260 [M+H]+ R/T = 3.51 min

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

Reference:
Patent; KUDOS PHARMACEUTICALS LIMITED; WO2008/23161; (2008); A1;,
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Application of 104618-31-7, 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. 104618-31-7, name is 2-(4-Hydroxycyclohexyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A solution of 4-phthalimido cyclohexanol (7.1 g, 0.029 mole) in dichloromethane (250 ml) was treated with pyridinium chlorochromate (8.6 g, 0.04 mole) and the resulting dark mixture was stirred at room temperature overnight. Diethyl ether (50 ml) was added and the mixture filtered through keiselguhr. The filtrate was concentrated in vacuo and the residue purified by column chromatography (SiO2; CHCl3 /EtOAc) to give 4-phthalimido cyclohexanone as a white solid (6.4 g).

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-(4-Hydroxycyclohexyl)isoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Smithkline Beecham plc; US5827871; (1998); A;; ; Patent; SmithKline Beecham P.L.C.; US5464864; (1995); A;,
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Synthetic Route of 169037-23-4,Some common heterocyclic compound, 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, molecular formula is C9H4F3NO3, 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.

5-TRIFLUOROMETHOXY-1H-INDOLE-2, 3-dione (3.48g, 15.0 MMOL) was dissolved in 2N aqueous sodium hydroxide (90MI) and cooled to 17 C before adding 30% aqueous hydrogen peroxide solution (2. 75ml, 27 MMOL) dropwise over 20 minutes. The mixture was stirred at room temperature for 1 hour before adding concentrated hydrochloric acid (7ml). The resulting brown precipitate was filtered off and DRIED IN VACUO at 50 C for 66 hours to give the title compound (1.83g) as a brown solid. APCI MS M/Z 220 [M-H] + 1H NMR (400MHZ, DMSO): 8 6.80 (d, 1H) 7.24 (dd, 1H), 7.53 (d, 1H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-(Trifluoromethoxy)indoline-2,3-dione, its application will become more common.

Reference:
Patent; PFIZER LIMITED; PFIZER INC.; WO2004/74291; (2004); A1;,
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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. 16800-68-3, name is 1-Acetylindolin-3-one, This compound has unique chemical properties. The synthetic route is as follows., category: indolines-derivatives

The N- acetyl-3-indolyl-one 1.75g (10mmol), N- benzyl-indole 2.07g (10mmol) and ferric chloride 1.62 g (10mmol) was dissolved in ethylene glycol and heated to 140 Celsius, 10 hours after the reaction, and extracted with methylene chloride, the organic layers combined, dried over anhydrous sodium sulfate, methylene chloride / methanol to give a white solid product N- acetyl -3- (indol-3-benzyl-N- ) – indole 3.1g, yield 85%

According to the analysis of related databases, 16800-68-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sun Yat-sen University; Weng, Jiang; Lu, Gui; Guo, Jing; (7 pag.)CN105669516; (2016); A;,
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Reference of 5332-26-3, These common heterocyclic compound, 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, 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.

Weigh Intermediate LNa-3 (0.1g, 0.4984mmol) in 50mL round-bottom flask was added dimethyl formamide (15mL) was dissolved with stirring at room temperature, was added sodium bicarbonate (0.0460g, 0.5482mmol) was stirred heated to 40 after 1.5h, then slowly added dropwise bromomethyl-N- phthalimide (0.2393g, 0.9968mmol) in dimethyl formamide dropwise completed (2h), TLC monitoring, the reaction is complete, the reaction is stopped, most of the solvent was distilled off, ethyl acetate (6mL) reconstituted added washed three times (3 ¡Á 5mL), saturated brine (5mL) wash, dried over anhydrous sodium sulfate, filtered, and the filtrate evaporated to dryness to give the crude product, and then with the volume fraction of 95% ethanol recrystallization, in pure LN-S-5.In various intermediate and LN-3-bromomethyl-N- phthalimide were prepared by the above process the compound LN-S-5 ~ target product LN-S-8, the results are as follows:

The synthetic route of 5332-26-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shandong University; Liu, Xinyong; Liu, Na; Zhan, Peng; Jia, Haiyong; (24 pag.)CN106008506; (2016); A;,
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These common heterocyclic compound, 100510-64-3, name is 3,3-Dimethyl-6-nitroindolin-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. Recommanded Product: 3,3-Dimethyl-6-nitroindolin-2-one

(e) 6-Amino-3,3-dimethylindolin-2-one A suspension of 146 g. (0.71 mol) 6-nitro-3,3-dimethylindolin-2-one in 3.5 liters methanol and 300 ml. glacial acetic acid are hydrogenated in the presence of 16 g. of 10% Pd/C at 40 C., while being well stirred. The clear solution obtained is filtered off with suction from the catalyst and the filtrate is evaporated. Yield: 125 g. (100% of theory); m.p. 185-190 C. The following compound is obtained in a manner analogous to that described in (e):

The synthetic route of 3,3-Dimethyl-6-nitroindolin-2-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Boehringer Mannheim GmbH; US4666923; (1987); A;,
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