Category: indolines-derivatives

Adding a certain compound to certain chemical reactions, such as: 39603-24-2, name is 5,7-Dimethylindoline-2,3-dione, 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 39603-24-2, COA of Formula: C10H9NO2

General procedure: To a hot solution of 4-(hydrazinecarbonyl)benzenesulfonamide 3 (0.25g, 1.16mmol) in glacial acetic acid (15mL), the appropriate isatin derivative 4a-h, 8a-g or 9a-c (1.2mmol) was added. This mixture was heated under reflux for 6h. The formed precipitate was filtered off while hot and washed with ethanol and petroleum ether then recrystallized from DMF/ethanol to obtain the target compounds 5a-h, 10a-g and 11a-c.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Abo-Ashour, Mahmoud F.; Eldehna, Wagdy M.; Nocentini, Alessio; Ibrahim, Hany S.; Bua, Silvia; Abou-Seri, Sahar M.; Supuran, Claudiu T.; European Journal of Medicinal Chemistry; vol. 157; (2018); p. 28 – 36;,
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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. 22190-33-6, name is 5-Bromoindoline, A new synthetic method of this compound is introduced below., category: indolines-derivatives

To a stirred solution of 5-bromo-indoline (3.0 g, 15 mmol) in acetonitrile (100 ml), was added DMAP (0.185 g, 1.522 mmol) and di-tert-butyl dicarbonate (3.98 g, 18.3 mmol) and the reaction was stirred at RT for 16 h. The reaction mixture was concentrated on reduced pressure to obtain a residue which was diluted with diethyl ether and washed with water and brine solution (2*). The combined ether layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford the crude product as an off-white solid, which was used in the next step without further purification (3.0 g).

The synthetic route of 22190-33-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dow AgroSciences LLC; Lo, William C.; Hunter, James E.; Watson, Gerald B.; Patny, Akshay; Iyer, Pravin S.; Boruwa, Joshodeep; US2014/171312; (2014); A1;,
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102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, 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. Computed Properties of C9H7NO3

General procedure: A solution of 9a-d (2 mmol), EDCI (3 mmol) and HOBt (3 mmol) in dry DCM (20 mL) was stirred at 0C for 3.5 h. Then different substituted amines (2.2 mmol) and DIPEA (4 mmol) were added and the reaction was stirred at r.t. for another 1.5 h. The organic layer was washed with water and brine and dried over Na2SO4. Removal of the solvent gave a residue that was purified by column chromatography (silica gel, CH2Cl2-MeOH 100: 1 as an eluent) to furnish 10a-n as white solids.

The synthetic route of 102359-00-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Guo, Jing; Zhu, Mingyue; Wu, Tianxiao; Hao, Chenzhou; Wang, Kai; Yan, Zizheng; Huang, Wanxu; Wang, Jian; Zhao, Dongmei; Cheng, Maosheng; Bioorganic and Medicinal Chemistry; vol. 25; 13; (2017); p. 3500 – 3511;,
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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. 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, A new synthetic method of this compound is introduced below., Quality Control of 5-(Trifluoromethoxy)indoline-2,3-dione

General procedure: A mixture of bisarylidenepiperidin-4-one (1.36 mmoL), isatin (2.72 mmoL) and L-phenylalanine (2.72 mmoL) were heated with stirring in [bmim]Br medium (3 mL) for 1 h at 100 C. After completion of the reaction (TLC), ethyl acetate (2 x 5 mL) was added and the reaction mixture was stirred for 10 min. The organic layer was removed under reduced pressure and the crude product was purified by column chromatography (ethyl acetate:hexane v/v 3:7). 5′-Benzyl-4′-phenyl-5-(trifluoromethoxy)spiro[3,2′]oxindolopyrrolidino-4′-phenyl-1?-styryl-5-benzylidenespiro[3′.3?]piperidin-4?-one (5a): Melting point 210-212 C; white solid, 94%; 1H-NMR (CDCl3, 400 MHz): delta/ppm 5.00 (d, J = 14.64 Hz, 1H), 4.68-4.72 (m, 1H), 4.34 (d, J = 10.24 Hz, 1H), 3.80 (d, J = 13.92 Hz, 1H), 3.68 (d, J = 16.92 Hz, 1H), 3.47 (d, J = 5.4 Hz, 1H), 3.02 (d, J = 11.72 Hz, 1H), 2.72-2.77 (dd, J = 13.96, 8.08 Hz, 1H), 2.54 (d, J = 13.92 Hz, 1H), 6.56-6.63 (m, 2H), 6.92-7.42 (m, 23H, Ar); 13C-NMR (CDCl3, 100 MHz): delta/ppm 39.6, 47.3, 52.8, 53.1, 61.0, 67.3, 70.8, 100.9, 109.7, 121.1, 122.5, 124.1, 124.4, 126.4, 127.3, 128.5, 128.6, 128.7, 128.8, 129.3, 129.6, 130.1, 130.4, 134.5, 136.9, 138.3, 138.4, 138.7, 139.7, 139.8, 144.4, 179.8, 197.1. EI-MS: m/z 711 (M+). Anal. Calcd for C44H36F3N3O3: C, 74.25; H, 5.10; N, 5.90. Found: C, 74.38; H, 5.17; N, 5.81.

The synthetic route of 169037-23-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Arumugam, Natarajan; Almansour, Abdulrahman I.; Kumar, Raju Suresh; Govindasami, Periyasami; Al-thamili, Dhaifallah M.; Krishnamoorthy, Rajapandian; Periasamy, Vaiyapuri Subbarayan; Alshatwi, Ali A.; Mahalingam; Thangamani, Shankar; Menendez, J. Carlos; Molecules; vol. 23; 5; (2018);,
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Synthetic Route of 6341-92-0,Some common heterocyclic compound, 6341-92-0, name is 6-Chloroisatin, molecular formula is C8H4ClNO2, 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 25-mL flask, equipped with a magnetic stirring bar, was charged with 2-(1,3-dithiolan-2- ylidene)acetonitrile 1a (143 mg, 1.0 mmol), isatin 2a (74 mg, 0.5 mmol), and MeCN (3.0 mL), followed by addition of a solution of I2 (25 mg, 0.1 mmol) in MeCN (1.0 mL). The reaction mixture was stirred at 80 C for 12 h. After 1a was consumed, as indicated by TLC, the reaction mixture was quenched with saturated aqueous Na2S2O3 (1.0 mL) and water (20.0 mL), and stirred for another 10 min. The fully precipitated solid was filtered and washed with water (20.0 mL). Then it was further washed with petroleum ether-ethyl acetate (1/1, V/V, 20.0 mL) and dried under vacuum to afford 3a.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Chloroisatin, its application will become more common.

Reference:
Article; Liang, Deqiang; Li, Xiangguang; Yang, Juan; Li, Yanni; Wang, Baoling; Cheng, Ping; Synthetic Communications; vol. 46; 23; (2016); p. 1924 – 1931;,
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Electric Literature of 13220-46-7, These common heterocyclic compound, 13220-46-7, name is 4-Methylindolin-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.

4-Methyl-3-(3-methyl-1H-indol-2-ylmethylene)-1,3-dihydro-indol-2-one A mixture of 4-methyl-2-oxindole (147 mg) (prepared as described in Compound IN-015), 3-methyl-indole-2-carbaldehyde (190 mg) (prepared according to Synthetic Communications, 1986, 16, 1799) and piperidine (10 mg) in ethanol was heated in a sealed tube at 95 C. for 4 hours. The mixture was cooled to room temperature. The solid was collected by vacuum filtration, washed with cold ethanol and dried in vacuum oven for overnight to give 4-methyl-3-(3-methyl-1H-indol-2-ylmethylene)-1,3-dihydro-indol-2-one. 1H NMR (360 MHz, DMSO-d6) delta13.07 (s, br, 1H, NH), 11.0 (s, br, 1H, NH), 7.78 (s, 1H, H-vinyl), 7.64 (d, J=8 Hz, 1H), 7.51 (d, J=8 Hz, 1H), 7.27 (dt, J=1, 8 Hz, 1H), 7.04-7.12 (m, 2H), 6.85 (d, J=8 Hz, 1H), 6.78 (d, J=8 Hz, 1H), 2.64 (s, 3H, CH3), 2.52 (s, 3H, CH3). MS El 288.

Statistics shows that 4-Methylindolin-2-one is playing an increasingly important role. we look forward to future research findings about 13220-46-7.

Reference:
Patent; SUGEN, Inc.; US2002/183364; (2002); A1;,
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Adding a certain compound to certain chemical reactions, such as: 64483-69-8, name is 5-Acetylindolin-2-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 64483-69-8, Application In Synthesis of 5-Acetylindolin-2-one

5-Ethyl-2-oxindole To 5-Acetyl-2-oxindole (2 g) in 15 mL of trifluoroacetic acid in an ice bath was slowly added 1.8 g of triethylsilane; the reaction was then stirred at room temperature for 5 hours. One mL of triethylsilane was added and the stirring continued overnight. The reaction mixture was poured into ice water and the resulting precipitate collected by vacuum filtration, washed copiously with water and dried under vacuum to give 1.3 g (71% yield) of the title compound as a yellow solid.

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

Reference:
Patent; SUGEN, Inc.; US2003/69421; (2003); A1;; ; Patent; Sugen, Inc.; US6051593; (2000); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 1035235-27-8, These common heterocyclic compound, 1035235-27-8, name is tert-Butyl 4-bromoisoindoline-2-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.

Step a. A suspension of 3-amino-N-methylisoquinoline-6-carboxamide TFA salt (Intermediate 6, 0.40 g, 1.262 mmol), tert-butyl 4-bromoisoindoline-2-carboxylate (Intermediate 1, 0.15 g, 0.505 mmol), and potassium tert-butoxide (0.28 g, 2.525 mmol) in toluene (10 ml) was degassed with nitrogen for 10 min at rt. BetaIotaNuAlphaRho (0.047 g, 0.050 mmol) and Pd2(dba)3 (0.032 g, 0.050 mmol) were added to the reaction mixture at rt. The reaction mixture was heated at 105C for 2 h. The resulting reaction mixture was cooled to rt, poured into water (20 ml) and extracted with EtOAc (2 x 40 ml). The combined organic phase was dried over Na2S04, filtered and concentrated under reduced pressure. The resulting residue was purified by flash chromatography (4% MeOH in DCM) yielding tert-butyl 4-((6-(methylcarbamoyl)isoquinolin-3-yl)amino)isoindoline-2-carboxylate (0.135 g, 0.322 mmol). LCMS: Method A, 2.278 min, MS: ES+ 419.5.

The synthetic route of 1035235-27-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MISSION THERAPEUTICS LIMITED; GIBSON, Karl Richard; JONES, Alison; KEMP, Mark Ian; MADIN, Andrew; STOCKLEY, Martin Lee; WHITLOCK, Gavin Alistair; WOODROW, Michael D; (241 pag.)WO2017/158388; (2017); A1;,
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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 141452-01-9 as follows. HPLC of Formula: C10H11NO2

1.26 g (5.8 mmoles) of di-tert-butyldicarbonate and 0.80 ml (5.8 mmoles) of Et3N are added successively at 20 C. to a solution of 0.85 g (4.8 mmoles) of methyl 5-indolinecarboxylate (J Heterocycl Chem (1993) 30 (4), 1133-1136) in 15 ml of CH2Cl2. The reaction mixture is stirred for 20 hours and concentrated to dryness under vacuum. The residue is divided between 50 ml of AcOEt and 25 ml of water. After stirring and decanting, the organic phase is washed with 25 ml of salt water, dried over MgSO4, filtered and concentrated to dryness under vacuum. The powder obtained is suspended in heptane, stirred and filtered in order to produce a white solid with a yield of 73%. Melting point=107-107.5 C.

According to the analysis of related databases, 141452-01-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Societe de Conseils de Recherches et d’Applications Scientifiques (S.C.R.A.S.); US6747024; (2004); B1;,
Indoline – Wikipedia,
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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. 104618-32-8, name is 2-(4-Oxocyclohexyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., category: indolines-derivatives

A solution of N-(4-oxocyclohexyl)phthalimide (14, 3.53 g, 15 mmol, 1 eq.) and 4-(methylsulfonyl)phenylhydrazine (2.70 g, 15 mmol, 1 eq.) in glacial acetic acid (110 mL) was heated at reflux for 47 h. The mixture was concentrated in vacuo and the residue was dissolved in CH2Cl2 (200 mL). Afterwards, the organic layer was washed with water (2 * 70 mL) and brine (70 mL), dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by fc with a gradient (? = 6 cm, l = 13 cm, v = 60 mL, cyclohexane/CH2Cl2 60:40, 50:50, 30:70, 0:100, CH2Cl2/methanol 100:10, Rf = 0.51 (cyclohexane/ethyl acetate/formic acid 3:7:0.2)). Pale yellow solid, mp 282-284 C, yield 4.50 g (79%). Purity (HPLC): 86.6% (tR = 19.6 min). C21H18N2O4S (394.5 g/mol). Exact mass (APCI): m/z = 395.1072 (calcd. 395.1060 for C21H19N2O4S [M + H+]). 1H NMR (600 MHz, DMSO-D6): delta (ppm) = 2.11 (d, J = 12.3 Hz, 1H, 2-H), 2.64-2.74 (m, 1H, 2-H), 2.92-3.01 (m, 3H, 1-CH2, 4-H), 3.12 (s, 3H, CH3), 3.29-3.33 (m, 1H, 4-H), 4.47-4.54 (m, 1H, 3-H), 7.49 (d, J = 8.6 Hz, 1H, 8-H), 7.56 (dd, J = 8.6/1.4 Hz, 1H, 7-H), 7.84-7.93 (m, 5H, 5-H, 4-Hphth, 5-Hphth, 6-Hphth, 7-Hphth), 11.45 (s, 1H, NH). 13C NMR (151 MHz, DMSO-D6): delta (ppm) = 22.5 (1C, C-1), 24.2 (1C, C-4), 26.2 (1C, C-2), 44.6 (1C, CH3), 47.4 (1C, C-3), 108.3 (1C, C-4a), 111.2 (1C, C-8), 117.3 (1C, C-5), 118.9 (1C, C-7), 123.0 (2C, C-4phth, C-7phth), 126.3 (1C, C-4b), 130.7 (1C, C-6), 131.5 (2C, C-3aphth, C-7aphth), 134.5 (2C, C-5phth, C-6phth), 136.8 (1C, C-9a), 138.5 (1C, C-8a), 167.9 (2C, C=O). FTIR (neat): ? (cm-1) = 3348 (m, N-H), 2939 (w, C-H, aliph), 1697 (s, C=O), 1620 (w, C-C, arom), 1130 (s, SO2).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 104618-32-8.

Reference:
Article; Heimann, Dominik; Boergel, Frederik; de Vries, Henk; Bachmann, Kim; Rose, Victoria E.; Frehland, Bastian; Schepmann, Dirk; Heitman, Laura H.; Wuensch, Bernhard; European Journal of Medicinal Chemistry; vol. 143; (2018); p. 1436 – 1447;,
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