Category: indolines-derivatives

Reference of 20870-78-4, A common heterocyclic compound, 20870-78-4, name is 5-Bromoindolin-2-one, molecular formula is C8H6BrNO, 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 solution of 5-bromo-2-oxindole (21 g, 100 mmol) in 1 ,4-dioxane (150 mL) was added bis(pinacolato)diboron (38 g, 150 mmol), l , l-bis(diphenylphosphino) ferrocene-palladium(II) dichloride dichloromethane complex (8.2 g, 10 mmol), and potassium acetate (20 g, 200 mmol). The resulting mixture was degassed and then stirred overnight at 80 C under an Ar atmosphere. After the reaction was completed as monitored by LC-MS, the mixture was diluted with water (500 mL) and then extracted with EtOAc. The combined organic layers were washed with water and brine, and then dried. The solvent was concentrated and the residue was purified by column chromatography (EtOAc / Pet = 2: 1) to give oxindole-5-boronic acid pinacol ester (15 g) as a white solid.

The synthetic route of 20870-78-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHENG, Zhanling; HAN, Xingchun; JIANG, Min; WANG, Jianhua; WANG, Min; YANG, Song; ZHOU, Chengang; WO2014/90692; (2014); 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. 954255-04-0, name is 5,6-Difluoroindoline, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C8H7F2N

Example 46 5-(6-(5,6-difluoroindoline-1-carbonyl)pyrimidin-4-ylamino)-1,3-dihydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-2′(1’H)-one 0.10 g (0.24 mmol) 6-(2′-oxo-1,1′,2′,3-tetrahydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-5-ylamino)pyrimidine-4-carboxylic acid hydrochloride, 50 mg (0.26 mmol) 5,6-difluoro-2,3-di-hydro-1H-indole, 0.10 mL (0.72 mmol) TEA and 80 mg (0.25 mmol) TBTU in 1.8 mL DMF were stirred overnight at RT. The purification was carried out by preparative HPLC-MS. The product-containing fractions were combined and lyophilised. Yield: 45 mg (36% of theory) ESI-MS: m/z=511 (M+H)+ Rt (HPLC-MS): 1.61 min (method C)

According to the analysis of related databases, 954255-04-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2011/21500; (2011); 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. 5181-35-1, name is 2-(2-Bromoethoxy)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 5181-35-1

To a solution of 2-(2-bromoethoxy)isoindoline- l,3-dione (20 g, 7 mmol, step 1 product) in dimethylformamide (100 ml) was added 1H- 1,2,4 triazole (5.2 g, 7.52 mmol) and cesium carbonate (26.5 g, 8.13 mmol) under stirring at 25-30 C. After 16 hours of stirring, the reaction mixture was filtered through filter paper and the filtrate was slowly poured into chilled water (700 ml) under stirring. After 30 minutes, the separated precipitates were filtered and washed with water (50 ml). The filtered precipitates were dried at 40C for 2 hour under high vacuum to provide 10.5 g of 2-[2- (lH- l,2,4-triazol- l-yl)ethoxy]- lH-isoindole- l,3(2H)-dione as white solid in 55% yield. Analysis: Mass: 259.2 (M+l) for Molecular weight: 258 and for Molecular formula: C12H10N4O3

According to the analysis of related databases, 5181-35-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; WOCKHARDT LIMITED; TADIPARTHI, Ravikumar; PATIL, Vijaykumar Jagdishwar; DEKHANE, Deepak; SHAIKH, Mohammad Usman; BIRAJDAR, Satish; DOND, Bharat; PATEL, Mahesh Vithalbhai; (100 pag.)WO2017/81615; (2017); A1;,
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Electric Literature of 20876-36-2, 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. 20876-36-2, name is 5-Aminoindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 1 A mixture of 5-aminooxindol (14 g), 29 g of bis(beta-bromoethyl)amine.hydrobromide in 250 ml of ethanol was stirred under reflux for 8 hours and allowed to stand overnight at room temperature. To the mixture was added sodium carbonate (10.1 g) and the mixture was stirred further for 8 hours under reflux. After cooling to room temperature, crystals which precipitated were collected by filtration and recrystallized from a mixture of water and ethanol to give 16 g of 5-(1-piperazinyl)oxindol.hydrobromide. Pale yellow powdery crystal NMR (200 MHz, DMSO-d6) delta: 3.30 (8H, s), 3.47 (2H, s), 6.78 (1H, d, J=8.5 Hz), 6.90 (1H, dd, J=8.5 Hz, 2 Hz), 7.04 (1H, d, J=2 Hz), 8.88 (2H, brs), 10.27 (1H, s)

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

Reference:
Patent; Otsuka Pharmaceutical Co., Ltd.; US4737501; (1988); A;,
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These common heterocyclic compound, 18711-13-2, name is 4,7-Dichloroindoline-2,3-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. HPLC of Formula: C8H3Cl2NO2

General procedure: A mixture of 1 (0.4 mmol), 2 (0.4 mmol), Na2CO3 (0.8 mmol) and TBHP (0.4 mmol) in DMF (4 mL) was stirred at rt for 2 h. Then, the mixture was poured into ice-water, acidified with 1 N HCl aq. (6 mL). The mixture was extracted with ethyl acetate (20 mL x 3). The combined organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by silica gel flash column chromatography to give desired products..

The synthetic route of 4,7-Dichloroindoline-2,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wu, Jun; Zhang, Hui; Ding, Xiao; Tan, Xuefei; Shen, Hong C.; Chen, Jie; He, Weimin; Deng, Hongmei; Song, Liping; Cao, Weiguo; Journal of Fluorine Chemistry; vol. 220; (2019); p. 54 – 60;,
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Related Products of 20870-79-5, 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. 20870-79-5, name is 5-Nitroindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Appel?s salt (Scheme 2, 1; 4,5-dichloro-1,2,3-dithiazolium chloride; 15.76 mmol) was added to asolution of each appropriate 2-oxindole derivative (Scheme 2, 2a-d; 14.33 mmol) in CH2Cl2 (20 mL).After a few minutes, the uncolored mixture turned to a dark red color, and was stirred at roomtemperature for 18 h. The solvent was evaporated under reduced pressure, and the crude productwas dissolved with acetone (a minimum of 30 mL), and then precipitated with water (300 mL).The heterogeneous mixture was filtered in a vacuum, and the red solid was washed three times withwater (25 mL). This solid was finally dried over phosphorus pentoxide in a vacuum in a desiccator.

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

Reference:
Article; Letribot, Boris; Delatouche, Regis; Rouillard, Herve; Bonnet, Antoine; Cherouvrier, Jean-Rene; Domon, Lisianne; Besson, Thierry; Thiery, Valerie; Molecules; vol. 23; 6; (2018);,
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Reference of 3485-84-5, A common heterocyclic compound, 3485-84-5, name is N-Vinylphthalimide, molecular formula is C10H7NO2, 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.

A 20-mL, microwave reaction vessel was charged with (4-bromopyridin-3-yl)-(4-(trifluoro methyl)phenyl)methanol (0.87 g, 2.62 mmol), 2-vinylisoindoline-1,3-dione (499 mg, 2.88 mmol), Pd(dba)2 (75.3 g, 0.13 mmol), 2-(dicyclohexyl-phosphino)biphenyl (91.8 mg, 0.26 mmol), NEt3 (0.44 ml, 3.14 mmol), and DMF (2 mL). The mixture was purged with argon and heated in microwave synthesizer at 150 C. for 1 h. The reaction mixture was partitioned between water and EtOAc. The EtOAc layer was separated and aqueous layer was extracted again with EtOAc. The combined organic layers were washed with saturated NaHCO3, dried over Na2SO4, filtered, and concentrated in vacuo. The resulting residue was purified by silica gel chromatography (0-10% MeOH in DCM) to give the mixture (0.4 g) of (E)-2-(2-(3-(hydroxy(4-(trifluoromethyl)phenyl)methyl)pyridin-4-yl)-vinyl) isoindoline-1,3-dione and 2-(2-(3-(hydroxy(4-(trifluoromethyl)phenyl)-methyl)pyridin-4-yl)ethyl)isoindoline-1,3-dione as a light yellow semi-solid. MS (ESI pos. ion) m/z: 425 and 427.

The synthetic route of 3485-84-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nishimura, Nobuko; Norman, Mark H.; Tamayo, Nuria; Tang, Phi; Bo, Yunxin Y.; US2009/82358; (2009); 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. 552330-86-6, name is 5-Bromoisoindolin-1-one, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 5-Bromoisoindolin-1-one

Step 1: Methyl 3-((1-oxoisoindolin-5-yl)thio)propanoate (0451) (0452) A solution of 5-bromoisoindolin-1-one (10 g, 47.16 mmol) in dioxane (450 mL) was degassed before Xantphos (2.73 g, 4.72 mmol), DIPEA (9.88 mL, 56.59 mmol), Pd2(dba)3 (2.159 g, 2.36 mmol) and methyl 3-mercaptopropanoate (32.6 mL, 330.12 mmol) was added. The reaction was heated to 80 C. for 1 h. The reaction was concentrated in vacuo. Approximately half of the material was purified by flash chromatography eluting with 0-5% methanol in EtOAc to afford 4.69 g of product. Only half the material was purified this way because the crude material solidified part way through loading onto the column. The solidified material was triturated with methanol and 4.48 g of product was collected by filtration as a colorless solid. The mother liquor was concentrated in vacuo and purified by flash chromatography eluting with 0-5% methanol in EtOAc to afford 1.1 g product. This was combined with the material from the first column to give 10.27 g (86%) of the title compound. (0453) LC/MS: m/z=252 [M+H]+. 1H NMR (500 MHz, DMSO) delta 2.69 (t, 2H), 3.26 (t, 2H), 3.60 (s, 3H), 4.34 (s, 2H), 7.38 (d, 1H), 7.52 (s, 1H), 7.58 (d, 1H), 8.48 (s, 1H).

According to the analysis of related databases, 552330-86-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AstraZeneca AB; NARJES, Frank; OLSSON, Roine Ingemar; VON BERG, Stefan; LEVER, Sarah; (112 pag.)US2017/166527; (2017); A1;,
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Synthetic Route of 480-91-1,Some common heterocyclic compound, 480-91-1, name is Isoindolin-1-one, molecular formula is C8H7NO, 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.

Sodium hydride 60% in mineral oil (0.750 mg, 30.0 mmol) and dry THF (150 ml) were added to a two-necked round-bottomed flask. Isoindolin-1-one (5) (2.50 g, 18.8 mmol) was added to the suspension at 0 C under N2. The reaction mixture wasstirred for 30 min at 0 C, and then potassium bromomethyl trifluoroborate (3.00 g, 15.0 mmol) was added to the reaction mixture in one portion and stirred for 30 min at 0 C. The reaction mixture was warmed to room temperature and refluxed for 48 h. The reaction mixture was cooled to 0 C and quenched by KHF2 (3.0 M) in H2O (14 mL). The reaction mixture was stirred at room temperature for 2 h. The solvents were removed under vacuum, and residue was dissolved in ethyl acetate (100 mL) and filtered. The solid obtained was triturated with boiling acetone (3 x 50 mL) and the resulting white powder was washed with cold ether (3 x 20 mL) and dried to give the potassium N-methyltrifluoroborate isoindolin-1-one (6) as white solid (2.54 g, 65%): mp: 229-234 C; IR (KBr, neat): 3032, 2936, 2897, 2879, 1658, 1590, 1473, 1455, 1426, 1415, 1306, 1228, 1210, 1099, 1069, 1011, 996, 760, 726, 538 cm-1; 1H NMR (DMSO-d6, 400 MHz) delta = 7.59 (d, J = 8.0 Hz, 1H), 7.53-7.46 (m, 2H), 7.42-7.39 (m, 1H), 4.38 (s, 2H), 2.47 (s, 2H); 13C NMR (DMSO-d6, 100 MHz) delta = 169.9, 144.0, 131.5, 131.2, 127.5, 123.7, 122.7, 44.8; 11B NMR (DMSO-d6, 128.37 MHz) delta = 3.46 (br s); 19F NMR (DMSO-d6, 376.49 MHz): delta = 138.67. HRMS (ESI-TOF) m/z calcd. for C9H8BNOF3 (M-K) 214.0651; found 214.0661.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Isoindolin-1-one, its application will become more common.

Reference:
Article; Nadaf, Rashid N.; Seapy, Dave G.; Synthetic Communications; vol. 44; 14; (2014); p. 2012 – 2020;,
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Synthetic Route of 1168150-46-6, These common heterocyclic compound, 1168150-46-6, name is (E)-Methyl 3-(methoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate, 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: A mixture of intermediate (3a, 3b, 6a, 6b, 10a, 10b, 11a-d, and14a-g, 1.5 mmol) and methyl (E)-3-(methoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate (1.5 mmol) in methanol (10 mL) wasstirred under reflux for 5-10 h. When TLC showed the completionof the reaction, the solution was cooled to room temperature. Theprecipitate was filtered off to give a crude product, which wasrecrystallized from methanol to provide the target compounds.

The synthetic route of 1168150-46-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Qin, Mingze; Tian, Ye; Sun, Xiaoqing; Yu, Simiao; Xia, Juanjuan; Gong, Ping; Zhang, Haotian; Zhao, Yanfang; European Journal of Medicinal Chemistry; vol. 139; (2017); p. 492 – 502;,
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