Tag: M.W=200-300

Adding some certain compound to certain chemical reactions, such as: 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, 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 2058-72-2. 2058-72-2

General procedure: A mixture of isatin (1.0 mmol), alpha-amino acid (1.0 mmol) and aroylacrylic acid (1.0 mmol) in 4.0 mL aqueous methanol(1:3) was heated in an oil bath to reflux temperature for about 20 min or stirred at room temperature from 25 min to 12 hours. The resulting precipitates were collected by filtration and washed with cold methanol to give analytically pure products 6.

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 5-Bromo-1-methylindoline-2,3-dione.

Reference:
Article; Pavlovskaya, Tatyana L.; Yaremenko, Fedor G.; Lipson, Victoria V.; Shishkina, Svetlana V.; Shishkin, Oleg V.; Musatov, Vladimir I.; Karpenko, Alexander S.; Beilstein Journal of Organic Chemistry; vol. 10; (2014); p. 117 – 126;,
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Adding some certain compound to certain chemical reactions, such as: 2436-29-5, name is 3-(1,3-Dioxoisoindolin-2-yl)propanal, 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 2436-29-5. 2436-29-5

To a solution of 2 (300 mg, 1.04 mmol) and 11a (317 mg, 1.56 mmol) in THF (30 mL) was added NH4OAc (802 mg, 10.4 mmol) in MeOH (30 mL). The reaction mixture was stirred at room temperature for 4 h. The reaction mixture was diluted with EtOAc and washed with a saturated aqueous solution of NaHCO3 and brine. The organic layer was dried over Na2SO4 and concentrated. The crude product was purified by column chromatography on silica gel eluting with 0-3% MeOH/CHCl3 to afford 2-{2-[5-(1,3-benzothiazol-6-yl)-4-(4-methyl-1,3-thiazol-2-yl)-1H-imidazol-2-yl]ethyl}-1H-isoindole-1,3(2H)-dione as a yellow solid (437 mg, 89%): MS (ESI) m/z 472 [M+H]+, 100%, 470 [M-H]-, 100%.

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 3-(1,3-Dioxoisoindolin-2-yl)propanal.

Reference:
Article; Amada, Hideaki; Sekiguchi, Yoshinori; Ono, Naoya; Koami, Takeshi; Takayama, Tetsuo; Yabuuchi, Tetsuya; Katakai, Hironori; Ikeda, Akiko; Aoki, Mari; Naruse, Takumi; Wada, Reiko; Nozoe, Akiko; Sato, Masakazu; Bioorganic and Medicinal Chemistry; vol. 20; 24; (2012); p. 7128 – 7138;,
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181140-34-1, 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 181140-34-1 as follows.

A mixture of 2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione (1) (0.640 g, 3.15 mmol), 2-chloro-4-methoxyphenol (2) (0.500 g, 3.15 mmol), and DBU (25 muL, 0.16 mmol) in p-xylene was heated at 120 C. for throughnight. The reaction mixture was cooled and then propan-2-ol (15 mL) and hydrazine (600 muL, 18.9 mmol) were added. The resulting mixture was heated at 90 C. for 5 h and cooled to room temperature. The reaction was diluted with 1 N NaOH (30 mL) and extracted with ethyl acetate (3¡Á20 mL). The combined extract was washed with 1 N NaOH (25 mL), dried through Na2SO4 and concentrated under reduced pressure to get crude (R)-1-amino-3-(2-chloro-4-methoxyphenoxy)propan-2-ol (3a) (0.547 g) which was used for next reaction without further purification. ESI-MS m/z 232.4 (M++1).

According to the analysis of related databases, 181140-34-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Gregor, Vlad E.; Liu, Yahua; Anikin, Alexey; McGee, Danny Peter Claude; Mikel, Charles; McGrath, Douglas Eric; Vavilala, Goverdhan Reddy; Pickens, Jason C.; Kadushkin, Alexander; Jiang, Luyong; Thiruvazhi, Mohan Santhanam; Zozulya, Sergey; Vairagoundar, Rajendran; Zhu, Tong; Chucholowski, Alexander; Webb, Thomas; Gantla, Vidyasagar Reddy; Yan, Zheng; US2008/171769; (2008); A1;,
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These common heterocyclic compound, 3335-98-6, name is 1-Phenyloxindole, 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. 3335-98-6

General procedure: The mixture of 2,4-dien-1-one (0.5 mmol), indolin-2-one (0.5 mmol, 66.5 mg) and cesium carbonate (0.25 mmol, 81.3 mg) in 3 mL of methylene chloride was stirred at room temperature for 40 min. After the completion monitored by TLC, the solid was filtered, and the liquor was concentrated under reduced pressure. The residue was isolated by column chromatography using petroleum ether and ethyl acetate (v/v 3:1) as eluent to give the pure product. The analytical data for products are given in Tables 1 and 2.

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 3335-98-6.

Reference:
Article; Song, Geyang; Li, Zheng; Chemical Papers; vol. 72; 6; (2018); p. 1379 – 1388;,
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883-44-3, Adding some certain compound to certain chemical reactions, such as: 883-44-3, name is 2-(3-Hydroxypropyl)isoindoline-1,3-dione, 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 883-44-3.

Step 2. Preparation of 3-(l,3-dioxoisoindolin-2-yl)propanal A mixture of 2-(3-hydroxypropyl)isoindoline-l,3-dione (2.0 g, 8.76 mmol) and IBX (8.2 g, 29.27 mmol) in 60 mL EA was refluxed for 2 h. The mixture was filtered and filtrate was concentrated to afford 3-(l,3-dioxoisoindolin-2-yl)propanal (2.0 g , yield: 100%) as white solid. NMR (500 MHz, CDC13): delta 9.82 (s, 2H), 7.84-7.86 (m, 2H), 7.72-7.74 (m, 2H), 4.04 (t, J = 7.0 Hz, 2H), 2.87-2.89 (m, 2H) ppm. MS (ESI): m/z 553.7 [M+l]+.

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 883-44-3.

Reference:
Patent; EPIZYME, INC.; CHESWORTH, Richard; KUNTZ, Kevin, Wayne; OLHAVA, Edward, James; PATANE, Michael, A.; WO2012/82436; (2012); A2;,
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These common heterocyclic compound, 15362-40-0, name is 1-(2,6-Dichlorophenyl)-2-indolinone, 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. 15362-40-0

General procedure: A finely ground mixture of 5-substituted indole-3-carboxaldehyde (1 mmol) and active methylene compound (indolinone/oxindole/barbituric acid/1-(3-chlorophenyl)-3-methyl-2-pyrazolin-5-one)/2-trifluoromethylbenzaldehyde (1.2 mmol) was irradiated in microwave oven for 1-5 min. The solid product was washed with diethyl ether and purified by column chromatography to get pure products 2-5 and 11-28 except compound 3. Compound 3 was prepared by treatment of 5-substituted indole-3-carboxaldehyde with indolinone in ethanol-water in presence of NaOH (1.5 mmol).

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 15362-40-0.

Reference:
Article; Shaveta; Singh, Palwinder; European Journal of Medicinal Chemistry; vol. 74; (2014); p. 440 – 450;,
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2058-72-2, The chemical industry reduces the impact on the environment during synthesis 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, I believe this compound will play a more active role in future production and life.

General procedure: A mixture of N-methylisatin 1a (161 mg, 1 mmol, 1 equiv), phenylacetylene 2a (0.12 mL, 1 mmol, 1.2 equiv), 1-aminoanthraquinone (0.266 g, 1 mmol, 1.2 equiv) 3a, cuprous chloride (9.9 mg, 10 mol %), and copper(II) triflate (36.1 mg, 10 mol %) in dry toluene (4 mL) was refluxed at 120 C for 24 h under nitrogen atmosphere. The progress of the reaction was monitored by TLC. After completion of the reaction, the mixture was cooled to room temperature, filtered through a pad of neutral alumina using ethyl acetate as a solvent. The solvent was evaporated in vacuo and the residue was chromatographed on neutral alumina using gradient elution of hexane/ethyl acetate as solvent to yield compounds 4a as pink powder, 183 mg, 39% yield and 5a as violet powder, 197 mg, 42% yield.

The chemical industry reduces the impact on the environment during synthesis 5-Bromo-1-methylindoline-2,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Article; Periyaraja, Somasundharam; Shanmugam, Ponnusamy; Mandal, Asit Baran; Senthil Kumar, Thiyagarajan; Ramamurthy, Perumal; Tetrahedron; vol. 69; 14; (2013); p. 2891 – 2899;,
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118289-55-7, 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. 118289-55-7 name is 6-Chloro-5-(2-chloroethyl)indolin-2-one, 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: Equimolar mixture of 6-chloro-5-(2-chloroethyl)-1,3-dihydro-2H-indol-2-one 1 (1.00mol) and the carbonyl compound (4i-x) (1.00mol) was stirred at RT in methanol (10mL) for 2h in presence of potassium carbonate (1.20mol). After completion, the reaction mass was filtered to remove inorganic salt, added methanol (10-20mL) and activated charcoal to the filtrate and stirred for 1hr. The crude product was filtered to remove charcoal, methanol was evaporated and cooled to 0-5C to get crude solid. Recrystallized using aqueous ethanol or methanol (Yield 60-70%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Chloro-5-(2-chloroethyl)indolin-2-one, and friends who are interested can also refer to it.

Reference:
Article; Meti, Gangadhar Y.; Kamble, Atulkumar A.; Kamble, Ravindra R.; Somagond, Shilpa M.; Devarajegowda; Kumari, Sandhya; Kalthur, Guruprasad; Adiga, Satish K.; European Journal of Medicinal Chemistry; vol. 121; (2016); p. 221 – 231;,
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Some common heterocyclic compound, 6326-79-0, name is 6-Bromoisatin, molecular formula is C8H4BrNO2, 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. 6326-79-0

General procedure: To mixture of isatins (1 mmol), malononitrile (1 mmol), and dimedone or 4-hydroxycoumarin or barbituric acids (1 mmol) in ethanol (4 mL), 5mg of Fe3O4APTPOSS MNPs added as the catalyst, and the mixture was stirred for an appropriate time at room temperature (Table 2). The reaction was monitored by TLC. After completion of the reaction, precipitate was filtered and dried in a drying oven to furnish 2-aminopyrano-3-carbonitriles.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6326-79-0, its application will become more common.

Reference:
Article; Safaei-Ghomi, Javad; Nazemzadeh, Seyed Hadi; Shahbazi-Alavi, Hossein; Catalysis Communications; vol. 86; (2016); p. 14 – 18;,
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883-44-3, The chemical industry reduces the impact on the environment during synthesis 883-44-3, name is 2-(3-Hydroxypropyl)isoindoline-1,3-dione, I believe this compound will play a more active role in future production and life.

Compound 359l-(3-((((2R^S,4R,5R)-5 6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2- yl)methyl)(isopropyl)amino)propyl)-3-(3-chlorophenyl)ureaStep 1. Preparation of 2-(3-((((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2- dimethyltetrahydrofuro[3,4-d][l,3]dioxol-4-yl)methyl)amino)propyl)isoindoline-l,3- dioneTo a solution of 2-(3-hydroxypropyl)isoindoline-l,3-dione (1.0 g, 4.88 mmol) in EA (50 mL) was added IBX (3.4 g, 12.19 mmol). The mixture was heated to reflux for 2h. After cooling, the mixture was filtered and the filtrate was concentrated to give 3-(l,3- dioxoisoindolin-2-yl)propanal crude (not weight), which was directly used for next step.To a solution of 9-((3aR,4R,6R,6aR)-6-(aminomethyl)-2,2- dimethyltetrahydrofuro[3,4-d][l,3]dioxol-4-yl)-9H-purin-6-amine (1.5 g, 4.90 mmol) and 3- (l ,3-dioxoisoindolin-2-yl)propanal (from last step) in DCE (50 mL) was added NaBH(OAc)3 (1.56 g, 7.30 mmol). The reaction mixture was stirred at rt overnight then saturated NaHC03 aqueous solution (50 mL) was added. The resulting mixture was extracted with DCM (50 mL x 2). The combined organic layers were dried over Na2S04 and concentrated. The residue was purified by SGC (DCM : MeOH = 100 : 1 to 10 : 1) to afford the title compound (1.38 g, yield: 57%) as a white solid. 1H NMR (500 MHz, MeOD): 58.30 (s, 1H), 8.23 (s, 1H), 7.85-7.79 (m, 4H), 6.17 (d, J = 2.5 Hz, 1H), 5.48 (dd, J = 2.5, 6.0 Hz, 1H), 5.03 (dd, J = 3.0, 6.5 Hz, 1H), 4.36 (t , J = 3.5 Hz, 1H), 3.67-3.65 (m, 2H), 2.94-2.89 (m, 2H), 2.62-2.60 (m, 2H), 1.82-1.79 (m, 2H), 1.60 (s, 9H), 1.39 (s, 3H) ppm; ESI-MS (m/z): 494.2 [M+l]+.

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

Reference:
Patent; EPIZYME, INC.; CHESWORTH, Richard; KUNTZ, Kevin, Wayne; OLHAVA, Edward, James; PATANE, Michael, A.; WO2012/82436; (2012); A2;,
Indoline – Wikipedia,
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