Month: May 2021

Some common heterocyclic compound, 21544-81-0, name is 4,6-Dimethoxyindoline-2,3-dione, molecular formula is C10H9NO4, 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: 21544-81-0

A solution of 4,6-dimethoxyindoline-2,3-dione(0.6g, 2.89 mmol) in NaOH (33% in water, 38 mL) was headedto 70 C. H2O2(30% in water, 9.4 mL) was added to the solutiondropwise. Themixture was maintained at 70 C for 40 min. Saturated Na2S2O3solution (30 mL) was added to the abovemixture at 10 C. The reactionmixture was adjusted to pH 8with HCl and then to pH 5 with AcOH. Theprecipitate thatformed was collected, washed with water, and dried to give compound11 (188 mg, 33%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 21544-81-0, its application will become more common.

Reference:
Article; Shao, Mingfeng; He, Linhong; Zheng, Li; Huang, Lingxiao; Zhou, Yuanyuan; Wang, Taijing; Chen, Yong; Shen, Mingsheng; Wang, Fang; Yang, Zhuang; Chen, Lijuan; Bioorganic and Medicinal Chemistry Letters; vol. 27; 17; (2017); p. 4051 – 4055;,
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Reference of 2058-72-2, A common heterocyclic compound, 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, molecular formula is C9H6BrNO2, 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: To a stirred mixture of 1-benzyl-1H-indole-2,3-dione (1a, 0.25 g,1.05 mmol), CuI (0.01 g, 0.05 mmol, 0.05 equiv), and phenylacetylene (2a, 0.11 g, 1.11 mmol, 1.05 equiv) in anhyd toluene (2 mL), DBU (0.032 g, 0.21 mmol, 0.2 equiv) was added at 25 C under a N2 atmosphere. Stirring was continued at this temperature until the starting material was completely consumed (TLC monitoring). After completion, the mixture was quenched with sat. aq NH4Cl (2mL) and extracted with EtOAc (2 × 5 mL). The combined organic layers were dried (anhyd Na2SO4) and evaporated under reduced pressure to dryness. The crude product thus obtained was purified by column chromatography (activated silica gel, 60-120 mesh, hexane-EtOAc) to afford pure 3aa as a white solid; yield: 0.35 g (97%); mp 177-179 C.

The synthetic route of 2058-72-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chouhan, Mangilal; Senwar, Kishna Ram; Kumar, Kapil; Sharma, Ratnesh; Nair, Vipin A.; Synthesis; vol. 46; 2; (2014); p. 195 – 202;,
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Related Products of 2058-74-4, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 2058-74-4 as follows.

General procedure: Amultimodereactor (Synthos 3000 Anton Paar, GmbH, 1400Wmaximum magnetron) was used. The initial step was conductedwith 4-Teflon vessels rotor (MF 100) that allowsthe reactions to process under the same conditions. Isatinderivatives 1a-1f and hydrazine hydrate 2a, thiosemicarbazide2b, or 4-aminobenzamide 2c were mixed together ina small portion of ethanol and then subjected to microwaveirradiation (400 watt). The vessels were heated for 5 min at100?C and held at the same temperature for another 5min.cooling was accomplished by a fan (5 min).The final productwas washed with cold ethanol and then dried under vacuumto afford the products 3a-3n in high yield and purity.

According to the analysis of related databases, 2058-74-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; El-Faham, Ayman; Hozzein, Wael N.; Wadaan, Mohammad A. M.; Khattab, Sherine N.; Ghabbour, Hazem A.; Fun, Hoong-Kun; Siddiqui, Mohammed Rafiq; Journal of Chemistry; vol. 2015; (2015);,
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Related Products of 6326-79-0, A common heterocyclic compound, 6326-79-0, name is 6-Bromoisatin, molecular formula is C8H4BrNO2, 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.

The solution of 6-bromoisatin (10 g, 22 mmol) in IN aqueous NaOH solution (48 mNo.) was stirred at 50 0C for 1 h. The mixture was cooled to 0 0C Sodium nitrite (3 g, 22 mmol) solution in water (11 m-6) was added drop wise for 15 min at 0 0C The mixture was added to the solution of water (90 mNo.) and sulfuric acid (4.6 mNo.) at 0 0C for 15 min. The mixture was added to the solution of cone, hydrochloric acid (40 m-6) and SnCl2.2H 2O (24 g, 53 mmol). After 1 h, the mixture was filtered and washed with water. The solid was dried through air flow to give the titled compound (8.98 g).[185] [186] 1H NMR (300 MHz, DMSOd6) delta 13.76 (bs, IH), 7.87 (s, IH), 7.55 (d, J = 8 Hz, IH), 7.27 (d, J = 8 Hz, IH), 2.44 (s, 3H).

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; KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; KOREA RESEARCH INSTITUTE OF BIOSCIENCE AND BIOTECHNOLOGY; SIM, Tae Bo; SON, Jung Beom; KIM, Hwan; PARK, Dong Sik; CHOI, Hwan Geun; HAM, Young Jin; HAH, Jung Mi; YOO, Kyung Ho; OH, Chang Hyun; LEE, So Ha; HA, Jae Du; CHO, Sung Yun; KWON, Byoung-Mog; HAN, Dong Cho; WO2010/64875; (2010); A2;,
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Reference of 3339-73-9, 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. 3339-73-9, name is 3-(1,3-Dioxoisoindolin-2-yl)propanoic acid, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: 1.0 mmol of (1,3-dioxoisoindolin-2-yl) acid, N-ethyl-N-dimethylaminopropylcarbodiimide (EDC) (1.1 mmol), hydroxybenzotriazole(HOBt) (1.2 mmol) and N,N-Diisopropylethylamine (2.0 mmol) weremixed in minimum DMF and the obtained mixture was stirred for5 min. Then, 4-aminoquinoline-diamines (1.0 mmol) was added to thereaction mixture and the stirring was continued for 5 h. The reactionend was proved by thin layer chromatography (TLC). Then, DMF wasevaporated using rotary evaporator and cold water (20 mL) was added,and solid precipitates obtained were filtered and washed with coldwater. The crude product was recrystallized in absolute ethanol.

The chemical industry reduces the impact on the environment during synthesis 3-(1,3-Dioxoisoindolin-2-yl)propanoic acid. I believe this compound will play a more active role in future production and life.

Reference:
Article; Rani, Anu; Legac, Jenny; Rosenthal, Philip J.; Kumar, Vipan; Bioorganic Chemistry; vol. 88; (2019);,
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In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 32692-19-6 as follows. Recommanded Product: 32692-19-6

Example 33: 4-(5-Nitroindolin-1 -yl)phenyl 2,3,4,6-tetra-O-acetyl-a-D-mannopyranosideTo a mixture of 4-iodophenyl 2,3,4,6-tetra-O-acetyl-a-D-mannopyranoside (18, 200 mg, 0.37 mmol), Cs2C03 (364 mg 1 .12 mmol) and 5-nitroindoline (91 .6 mg, 0.56 mmol) in a Schlenk tube under argon, x-Phos (9.1 mg, 0.019 mmol) and Pd2(dba)3 (3.85 mg, 0.0037 mmol), which had been pre-stirred for 15 min at 40C in dry toluene (3.5 mL), are added. The reaction mixture is degassed in an ultrasonic bath and stirred 140 h at 80C. The reaction mixture is diluted in EtOAc (50 mL) and washed with aqueous satd. NaHC03 solution (2 x 50-100 mL) and brine (50-100 mL). The aqueous layers are each extracted with EtOAc (2 x 50-100 mL) and the combined organic layers are dried over Na2S04, filtered and concentrated under reduced pressure. 20 (163 mg, 75%) is obtained as an orange solid after silica gel chromatography (5-40% gradient of EtOAc in petrol ether). [a]D20 +55 (c = 1 , CHCIs); 1H NMR (CDCI3): delta 2.02 (s, 3H, OAc), 2.04 (s, 6H, 20Ac), 2.18 (s, 3H, OAc), 2.20 (s, 3H, OAc), 3.19 (t, J = 8.6 Hz, 2H, CH2), 4.08 (m, 4H, CH2, H-6a, H- 5), 4.28 (dd, J = 5.2, 12.5 Hz, 1 H, H-6b), 5.38 (t, J = 10.1 Hz, 1 H, H-4), 5.44 (dd, J = 1.8, 3.5 Hz, 1 H, H-2), 5.50 (d, J = 1 .6 Hz, 1 H, H-1 ), 5.55 (dd, J = 3.5, 10.1 Hz, 1 H, H-3), 6.73 (d, J = 8.9 Hz, 1 H, C6H4, C6H3 ) 7.13 (m, 3H, C6H4, C6H3 ), 7.21 (m, 1 H, C6H4, C6H3), 7.95 (s, 1 H, C6H3, C6H4 ), 7.98 (dd, J = 2.3 Hz, 8.9 Hz, 1 H, C6H3, C6H4 ); 13C-NMR (CDCI3): delta 20.90, 20.92, 21 .09, 21 .65 (40Ac), 27.27 (CH2), 53.85 (CH2), 62.28 (C-6), 66.03 (C-4), 68.98 (C-3), 69.40 (C-2), 69.53 (C-5), 96.36 (C1 ), 105.52 (C6H4), 1 17.81 ,1 17.92 (C6H4, C6H3), 121 .32 (C6H3), 122.03 (C6H4), 126.27 (C6H3), 128.40 (C6H3), 137.21 (Car-N) , 169.90, 170.19, 170.23, 170.70 (C=0); ESI-MS calcd. for C28H31N20i2 [M+H]+: 587.19; found 587.29.

According to the analysis of related databases, 32692-19-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UNIVERSITY OF BASEL; ERNST, Beat; HEROLD, Janno; WO2011/73112; (2011); A2;,
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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. 3891-07-4, name is 2-(2-Hydroxyethyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., name: 2-(2-Hydroxyethyl)isoindoline-1,3-dione

PREPARATION 7 Preparation of ethyl 4-[2-(phthalimido)ethoxy]acetoacetate STR52 Sodium hydride (57% [by weight] in oil, 66.1 g) was stirred in dry tetrahydrofuran (500 ml) under nitrogen at -10 while N-(2-hydroxyethyl)phthalimide (150 g) was added. To this slurry was added at -10 a solution of ethyl 4-chloroacetoacetate (129.3 g), in dry tetrahydrofuran, over 1 hour. The reaction mixture was then allowed to warm to room temperature and stirring was continued for 18 hours. This mixture was poured into 1N hydrochloric acid (800 ml) and ethyl acetate was added (750 ml). The aqueous layer was washed with ethyl acetate (300 ml) and the organic solutions were combined. After washing with water (300 ml), the ethyl acetate was evaporated to give the title compound as a crude oil (243 g), sufficiently pure for further use.

According to the analysis of related databases, 3891-07-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pfizer Inc.; US4572909; (1986); A;,
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Reference of 22190-33-6, 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. 22190-33-6 name is 5-Bromoindoline, 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.

1 , 1 -Dimethylethyl 5-bromo-2,3-dihvdro-1 H-indole-1 -carboxylateTo a stirred solution of 5-bromo-2,3-dihydro-1 H-indole (30 g, 151 mmol) and DMAP (0.4 g, 3.27 mmol, 0.02 equiv) in 150 mL of MeCN at room temperature was added Boc20 (43 g, 197 mmol, 1.3 equiv) in one portion. The mixture was stirred at rt. After 10 min, the mixture gradually became a suspension. After 3 h, the suspension was filtered. The cake was washed with cold MeCN (60 mL), and sucked under house vacuum for 5 h to give 1 , 1 -Dimethylethyl 5-bromo-2,3-dihydro-1 H-indole-1 -carboxylate (ca 28.5 g prior to drying). LCMS (ES) m/z = 244, 242 as prominent fragments. 1 H NMR (400 MHz, DMSO-d6) ppm 1 .50 (s, 9 H), 3.06 (t, J=8.7 Hz, 2 H), 3.91 (t, J=8.7 Hz, 2 H), 7.31 (dd, J=8.5, 1.9 Hz, 1 H), 7.38 (s, 1 H), 7.51 – 7.71 (br s, 0.6 H).

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

Reference:
Patent; GLAXOSMITHKLINE LLC; AXTEN, Jeffrey, Michael; GRANT, Seth, Wilson; HEERDING, Dirk, A.; MEDINA, Jesus, Raul; ROMERIL, Stuart, Paul; TANG, Jun; WO2011/119663; (2011); A1;,
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Adding a certain compound to certain chemical reactions, such as: 6872-06-6, name is 2-Methylindoline, belongs to indolines-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 6872-06-6, name: 2-Methylindoline

General procedure: In a 2-neck RBF, 1 (20 mg, 0.0005 mmol) and TMNO (45 mg, 0.6 mmol) were suspended in toluene (4 mL) and to this solution indoline (60 mg, 0.5 mmol) was added. The reaction mixture was then heated to 100 oC for 20 h and it was filtered and solvent evaporated. The crude product obtained was purified by column chromatography using hexane/ethylacetate (7:1) as eluent to give pure indole (47 mg, 79%). A similar procedure was used for the other indolines and N-heterocycles.

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

Reference:
Article; Kumaran, Elumalai; Leong, Weng Kee; Tetrahedron Letters; vol. 59; 44; (2018); p. 3958 – 3960;,
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Adding a certain compound to certain chemical reactions, such as: 480-91-1, name is Isoindolin-1-one, belongs to indolines-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 480-91-1, category: indolines-derivatives

Example 7: Illustrative Preparation of 5-member Glutarimide Scheme 23: (1973) (1974) Step-1 To a stirred solution of 23-2 (448 mg, 3.37 mmol) and 23-1 (1000 mg, 3.37 mmol) and Potassium carbonate (931 mg, 6.74 mmol) in Acetone (20.0 mL ). It was stirred at room temperature for 16 hours. It was diluted with water and extracted with ethyl acetate. Organic part was dried over sodium sulfate, concentrated under reduced pressure and purified by column chromatography using (silica, gradient, 0%-30% ethyl acetate in hexane to afford 3 as off white solid. Yield-20%; LC MS: ES+ 349.3.

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

Reference:
Patent; C4 THERAPEUTICS, INC.; PHILLIPS, Andrew, J.; NASVESCHUK, Chris, G.; HENDERSON, James, A.; LIANG, Yanke; CHEN, Chi-li; DUPLESSIS, Martin; HE, Minsheng; LAZARSKI, Kiel; (980 pag.)WO2017/197051; (2017); A1;,
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