Category: indolines-derivatives

Some common heterocyclic compound, 675109-26-9, name is 6-Bromoisoindolin-1-one, molecular formula is C8H6BrNO, 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. SDS of cas: 675109-26-9

O2O3] &bromoisoindolin4-orse (1050 mg, SM m.mol% copper powder (32 mg, 0.5 mmol) and methylamine (40% in F120, 2.7 mL) were placed in a pressure vess& and the sealed reaction was heated at 105 C overnight. The reaction mixture was poured into ethyl acetate (150 niL) and washed with saturated NH4CI solution. The organic layer was dried over sodium sulfate, filtered and concenflted. The volatile was removed in vacua and the residue was then purified by silica gel chromatography eluting with MeOH and dichloromethane Rf 0.2, 5% MeOH in DCIVO to afford 300mg of the title compound. MS (m/z): 163.13 [M+H]t HPLC retention time 0.17 mm (248% acetonitrile: water with 0.05% trifluoroacetie acid). ?H NMR (400 MHz, dmso) 8 8.28 (s 1K), 7.20 (d, J= 8.2 Hz, 1H), 6.75 (dd, J 8.2, 2.2 Hz5 lH), 6.68 (d, J= 2.1 Hz, 1K), 5.83 (d, J 5.0 Hz, IH), 4.15 (s, 2K), 2.66 (d, J= 5,1 Hz, 3Ff).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 675109-26-9, its application will become more common.

Reference:
Patent; GILEAD SCIENCES, INC.; BONDY, Steven, S.; CHOU, Chien-Hung; LINK, John, O.; TSE, Winston, C.; WO2015/130964; (2015); A1;,
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Electric Literature of 169037-23-4, 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. 169037-23-4 name is 5-(Trifluoromethoxy)indoline-2,3-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.

General procedure: To the reaction mixture containing isatin (0.5mmol) in water (2mL), indole (0.5mmol), diethanolamine (20mol %) was slowly added at room temperature. After thecompletion of reaction as monitored by TLC, the reaction mixture was washed with brine solution and then extracted with ethyl acetate. The organic layer was dried over anhydrous Na2SO4 and the product was purified by flash chromatography on the silica gel column using a gradient of petroleum ether/ethyl acetate, as eluent to afford pure products 1-41.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-(Trifluoromethoxy)indoline-2,3-dione, and friends who are interested can also refer to it.

Reference:
Article; Sai Prathima, Parvathaneni; Rajesh, Pamanji; Venkateswara Rao, Janapala; Sai Kailash, Uppalapati; Sridhar, Balasubramanian; Mohan Rao, Mandapati; European Journal of Medicinal Chemistry; vol. 84; (2014); p. 155 – 159;,
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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.

Preparation 1 2-{2-[4-(2-Hvdroxy-ethvD-phenyl1-vinyl)-isoindole-1 ,3-dione; To a solution of 2-(4-bromophenyl)ethanol (48.3g) in acetonitrile (480 ml) were added diisopropylethylamine (46.6g), N-vinylphthalimide (43.7g) and tri-o-tolylphosphine (7.31g) and the mixture was purged with nitrogen gas three times. Palladium acetate (2.7g) was added and the mixture was stirred at 9O0C for 21 hours under nitrogen. The reaction was cooled and the precipitated product collected by filtration. The resulting solid was re-dissolved in dichloromethane and ethyl acetate and filtered through silica gel. The filtrate was concentrated in vacuo to give the title compound, 24g. 1H NMR (400MHz, CDCI3) delta = 2.81 -2.84 (t, 2H), 3.82-3.90 (t, 2H), 7.23-7.26 (d, 2H), 7.32-7.36 (d, 1 H), 7.40-7.43 (d, 2H), 7.61-7.64 (d, 1 H), 7.66-7.78 (d, 2H), 7.86-7.88 (d, 2H) ppm.

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:
Patent; PFIZER LIMITED; GLOSSOP, Paul Alan; LANE, Charlotte Alice Louise; WO2010/7561; (2010); A1;,
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Application of 102359-00-2,Some common heterocyclic compound, 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, molecular formula is C9H7NO3, 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.

An oven-dried round-bottom flask was charged with 2-oxoindoline-5- carboxylic acid (89 mg, 0.500 mmol), TBTU (193 mg, 0.600 mmol), HOBt hydrate (81 mg, 0.600 mmol), DIPEA (0.13 mL, 0.750 mmol) and DMF (3.0 mL) and stirred for 5 minutes. Methyl amine (0.75 mL of a 2.0 M solution in THF) was then added and reaction was stirred for 4 hours at which time NaHCO3(Sat ) (2mL) was added. Solvents were removed in vacuo and the residue was purified by column chromatography (silica gel, 92:8 CH2Cl2ZMeOH) to give the title compound (11 mg, 12 %). IH NMR (400 MHz, CD3OD) delta ppm 7.69 – 7.75 (m, 2 H), 6.94 (d, J=8.1 Hz, 1 H), 3.58 (s, 2 H), 2.97 (s, 3 H); MS ESI 191.0 [M + H]+, calcd for [C10H10N2O2 + H]+ 191.08.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Oxoindoline-5-carboxylic Acid, its application will become more common.

Reference:
Patent; UNIVERSITY HEALTH NETWORK; WO2009/79767; (2009); A1;,
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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. 32692-19-6, name is 5-Nitroindoline, A new synthetic method of this compound is introduced below., Formula: C8H8N2O2

(a) 1-Methyl-5-nitroindoline. To a round-bottomed flask equipped with magnetic stirring was added 5-nitroindoline (0.82, 5.0 mmol, Aldrich), iodomethane (0.71 g, 5.0 mmol, Aldrich), sodium hydroxide (0.24, 6 mmol) and DMF (20 mL). The reaction mixture was stirred at 25 C. for 3 h, diluted with water (50 mL), extracted with EtOAc (3*40 mL) and the combined extracts were concentrated in vacuo. Purification by silica gel chromatography 97:3 hexane:EtOAc) provided the title product. MS (ESI, pos. ion) m/z: 179 (M+1).

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; Bo, Yunxin Y.; Chakrabarti, Partha P.; Chen, Ning; Doherty, Elizabeth M.; Fotsch, Christopher H.; Han, Nianhe; Kelly, Michael G.; Liu, Qingyian; Norman, Mark Henry; Ognyanov, Vassil I.; Wang, Xianghong; Zhu, Jiawang; US2003/195201; (2003); A1;,
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Related Products of 340702-10-5, 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. 340702-10-5, name is 6-Fluoroisoindolin-1-one, This compound has unique chemical properties. The synthetic route is as follows.

To a 0 C. suspension of 6-fluoroisoindoline-1-one (8.0 g, 5.3 mmol) in concentrated H2SO4 was added drop-wise a pre-cooled mixture of concentrated H2SO4 (26 mL) and nitric acid (6 mL) while keeping the reaction mixture below 5 C. After addition, the reaction mixture was slowly warmed to room temperature during overnight. Ice (50 g) was added to the mixture and the solid was collected and dried, then washed with MTBE (50 mL) and ethyl acetate (50 mL) to give the desired product as a light yellow solid (5.1 g, 50%). MS: (ES) m/z calculated for C8H6FN2O3[M+H]+ 197, found 197.

The chemical industry reduces the impact on the environment during synthesis 6-Fluoroisoindolin-1-one. I believe this compound will play a more active role in future production and life.

Reference:
Patent; CHEMOCENTRYX, INC.; CHEN, Xi; DRAGOLI, Dean R.; FAN, Junfa; KALISIAK, Jaroslaw; LELETI, Manmohan Reddy; MALATHONG, Viengkham; McMahon, Jeffrey; TANAKA, Hiroko; YANG, Ju; YU, Chao; ZHANG, Penglie; Mali, Venkat; (62 pag.)US2017/144996; (2017); 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. 2518-24-3, name is 4-Aminoisoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 4-Aminoisoindoline-1,3-dione

In a 2500 mL round bottom flask containing 0.62 mol (100 g) of 3-aminophthalimide, Add anhydrous ethanol 800mL, 455 mL of a methanol solution of KOH at a concentration of 80 g · L-1 (1 h addition, 0.65 mol KOH) was added dropwise with stirring. Continue stirring at room temperature for 3h, filter, The resulting white solid was rinsed with absolute ethanol, drying, The quality is 114g.

According to the analysis of related databases, 2518-24-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chinese Academy Of Agricultural Sciences Plant Protection Institute; Mei Xiangdong; Si Weijie; Zhang Tao; Ning Jun; (17 pag.)CN104447498; (2017); B;,
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Related Products of 22190-33-6, The chemical industry reduces the impact on the environment during synthesis 22190-33-6, name is 5-Bromoindoline, I believe this compound will play a more active role in future production and life.

5-Bromoindoline (3.96 g, 20 mmol), di-t-butylcarbonate (4.37 g, 20 mmol), 4-dimethylaminopyridine (2.69 g, 22 mmol) and CH3CN (50 mL) were mixed and stirred at room temperature for 16 h. The reaction mixture was diluted with EtOAc (300 mL) and the organic solution was washed successively with water (50 mL), a 1 N HCl solution (50 mL), a saturated NaHCO3 solution (2×50 mL) and brine (25 mL). The organic layer was dried over MgSO4, filtered and concentrated in vacuo to afford a solid. Trituration with hexane and drying in vacuo provided a white solid (2.26 g, 38% yield): 1H NMR (DMSO-d6, 300 MHz): 7.36 (s, 1H), 7.29 (d, 2H, J=7), 3.86 (t, 2H, J=7), 3.04 (t, 2H, J=7), 1.48 (s, 9H).

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, 5-Bromoindoline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Gilligan, Paul J.; US2006/63799; (2006); A1;,
Indoline – Wikipedia,
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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. Recommanded Product: 480-91-1

General procedure: Isoindolin-1-one (200 mg, 1.50mmol) was dissolved in super-dry DMSO (4 mL), and Cs2CO3 (1215 mg, 3.75 mmol), CuI (58 mg, 0.30mmol) and N1,N2-dimethylethane-1,2-diamine (27 mg, 33 muL, 0.30 mmol) were added to the solution.The resulting mixture was stirred at room temperature for 10 min, after which iodobenzene (2.25mmol) was added. Then the mixture was heated to 120 C. When TLC showed that isoindolin-1-onehad been fully converted, the reaction was stopped. The mixture was extracted with ethyl acetate (20mL) and H2O (10 mL). The water phase was re-extracted with ethyl acetate (20 mL). The organic layerwas combined and washed with brine (10 mL). Then the solution was dried over anhydrous MgSO4,filtered and concentrated, and the crude residue was purified by flash chromatography over silica gelusing CH2Cl2/CH3OH as the gradient elution to afford the title compounds.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 480-91-1, its application will become more common.

Reference:
Article; Wang, Yixuan; Wang, Huiqiang; Jiang, Xinbei; Jiang, Zhi; Guo, Tingting; Ji, Xingyue; Li, Yanping; Li, Yuhuan; Li, Zhuorong; Molecules; vol. 24; 5; (2019);,
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Related Products of 19727-83-4, A common heterocyclic compound, 19727-83-4, name is 6-Nitroindoline, molecular formula is C8H8N2O2, 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.

9.84 g (0.06 mol) of 6-nitro-2,3-dihydro-1H-indole (16) was dispersed in 100 ml of dichloromethane under a nitrogen atmosphere, stirred at room temperature for about 10 minutes,11.8 g (0.12 mol) of cyclohexanone, 8.6 ml (0.15 mol) of acetic acid,29.7 g (0.14 mol) of sodium triacetoxy borohydride were added in this order, and the reaction solution was reacted at room temperature for 4 hours.200 ml of 1 N aqueous sodium hydroxide solution was slowly added to the reaction mixture, and the mixture was stirred for 30 minutes. The organic layer was separated, washed with H2O,The recovered organic layer was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The resulting product was dispersed in 100 ml of methanol, stirred at room temperature for 30 minutes, filtered and dried to obtain 6-nitro-2,3-dihydro -1-cyclohexyl-1H-indole (55) (12.7 g, 86.0%).

The synthetic route of 19727-83-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Korea Research Institute of Chemical Technology; Shin Seung-rim; Jeon Geun; Shin Jong-il; Park Yeong-il; Ahn Gyeong-ryong; (48 pag.)KR101842495; (2018); B1;,
Indoline – Wikipedia,
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