Tag: M.W=200-300

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. 99365-40-9 name is 6-Bromoindolin-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. 99365-40-9

Commercially available 6-bromoxindole (656 mg), zinc cyanide (288 mg) and tetrakis triphenylphosphine palladium(0) (175 mg) were suspended in dry N,N-dimethylformamide (6 mL). The resulting mixture was degassed by three pump/vent cycles with argon and then placed in a preheated oil bath (80 C.). After stirring at this temperature for 15 h the mixture was cooled to room temperature, diluted with water (60 mL) and extracted with ethyl acetate (3¡Á60 mL). The combined organic layers were washed with water (2¡Á60 mL), dried (MgSO4), filtered and concentrated. The remaining residue was purified by flash chromatography (silica, dichloromethane/methanol) to afford the title compound (385 mg; 81%). [MH]+=159.

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

Reference:
Patent; Alantos Pharmaceuticals, Inc.,; US2006/173183; (2006); A1;,
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A common compound: 99365-40-9, name is 6-Bromoindolin-2-one, belongs to indolines-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 99365-40-9

To a suspension of potassium tert-butylate (12.8 g) in dry THF (80 ml) was added portion wise at 0 C 6-bromoindolin-2-one (5.0 g,) followed by copper (I) bromide-dimethylsulfide complex(470 mg). Mel (6.82 g) was added drop wise within 45 mm keeping the internal temperature below 8 C, the mixture was warmed to 22 C and stirring was continued for 16 hours. The mixture was quenched at 0 C with saturated aqueous ammonium chloride solution and diluted with TBME and water. The organic layer was dried, evaporated and the residue purified by flash chromatography (silica gel, EtOAc/ n-heptane, 1:1) to give the title compound (5.17 g) as abrown solid (5.17 g, 9 1%). MS (mlz): 240.4/ 242.4 [(M+H)?i.

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, 99365-40-9, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HILPERT, Hans; KOLCZEWSKI, Sabine; HUMM, Roland; STOLL, Theodor; MUSER, Thorsten; PLANCHER, Jean-Marc; GAUFRETEAU, Delphine; (142 pag.)WO2015/197567; (2015); 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 675109-26-9 as follows. 675109-26-9

Preparation 42: 6-bromo-2-[(3-methyloxetan-3-yl)methyl]-2,3-dihydro-1 H-isoindol-1 -one (1538) (1539) A stirred suspension of 6-bromo-2,3-dihydro-1 H-isoindol-1 -one (300 mg, 1.42 mmol) in DMF (4 mL) was cooled in an ice-bath and treated with sodium hydride (60% dispersion in mineral oil, 68 mg, 1.70 mmol) and stirred and cooled for 15 min. The mixture was treated with 3- (bromomethyl)-3-methyloxetane (280 mg, 1.70 mmol) and stirred at RT for 18 h. Brine (20 mL) was added and the crude product was extracted with ethyl acetate (2x 20 mL). The combined extracts were washed with brine (20 mL), dried (MgS04) and evaporated. The residue was purified by chromatography (S1O2, 20-100% ethyl acetate in /so-hexane) to afford the title compound (342 mg, 81 %) as a yellow solid. LC-MS: [M+H]+ = 296/ 298.

According to the analysis of related databases, 675109-26-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; BERDINI, Valerio; BUCK, Ildiko Maria; DAY, James Edward Harvey; GRIFFITHS-JONES, Charlotte Mary; HEIGHTMAN, Thomas Daniel; HOWARD, Steven; MURRAY, Christopher William; NORTON, David; O’REILLY, Marc; WOOLFORD, Alison Jo-Anne; COOKE, Michael Liam; COUSIN, David; ONIONS, Stuart Thomas; SHANNON, Jonathan Martin; WATTS, John Paul; (867 pag.)WO2017/68412; (2017); A1;,
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6326-79-0, name is 6-Bromoisatin, 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. 6326-79-0

To a solution of compound 9 (10 g, 44.44 mmol) in EtOH (130 mL) was added a solution of hydroxylamine hydrochloride (4.61 g, 66.37 mmol) in H2O (20 mL), and the mixture was stirred at 80 C. for 12 h. The mixture was concentrated under reduced pressure and the solid formed was filtered, washed with cold water, and dried under high vacuum to afford 10.24 g (96%) of compound 10 as a blood-red solid. IR (KBr) numax. cm-1: 3336, 3330 (NH2), 3310 (OH), 3038 (Ar-H), 2920 (Alph-H), 1690 (C?O), 1612, 1515, 1414 (C?C), 1260 (C-N). 1H NMR (500 MHz, DMSO-d6) delta=7.02 (s, 1H, H-7); 7.20 (d, 1H, J=8.2 Hz, H-5); 7.84 (d, 1H, J=8.1 Hz, H-4); 10.83 (s, 1H, NH); 13.49 (s, 1H, OH); 13C NMR (125.7 MHz, DMSO-d6) delta=113.12 (aromatic-C), 115.50 (aromatic-C), 124.84 (aromatic-C), 128.46 (aromatic-C), 143.48 (aromatic-C), 144.02 (aromatic-C), 164.29, 167.12 (C?O). Calculated (%) for C8H5BrN2O2(239.95); C, 39.86; H, 2.09; N, 11.62. found (%); C, 39.80; H, 2.14; N, 11.58.

Statistics shows that 6326-79-0 is playing an increasingly important role. we look forward to future research findings about 6-Bromoisatin.

Reference:
Patent; King Fahd University of Petroleum and Minerals; King Abdulaziz City for Science and Technology; Ullah, Nisar; US8916704; (2014); B1;,
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2058-72-2, 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.

To a stirred mixture of isocyanoacetate 1 (0.12 mmol),2-MeOC6H4CO2H (10 mol%), 4a (10 mol%), and AgPF6 (11 mol%)in THF (0.5 mL) was added isatin 2 (0.1 mmol) and THF (0.5 mL)at 0 C. The reaction was then allowed to proceed at 0 C for 4-6h. Upon completion, the reaction mixture was purified by flashchromatography on silica gel to afford the desired product.Analytical data of some typical compounds:

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 2058-72-2.

Reference:
Article; Lu, Yan; Wang, Min; Zhao, Xiaohu; Liu, Xiaohua; Lin, Lili; Feng, Xiaoming; Synlett; vol. 26; 11; (2015); p. 1545 – 1548;,
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675109-26-9, A common compound: 675109-26-9, name is 6-Bromoisoindolin-1-one, belongs to indolines-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

General procedure: Bromoisoindolin-1-one (2.0 g, 9.43 mmol) was dissolved with warming in DMF (150 mL),then cooled to 0C. NaH (415 mg, 10.4 mmol) was added and the mixture stirred under N2 at 0C for 0.5 h. Methyl iodide (0.65 mL, 10.4 mmol) was added dropwise and the reaction allowed to warm to room temperature and stir for another I h. A small quantity of water was added to quench the reaction then the DMF removed under reduced pressure to give an oily yellow residue which was dissolved in EtOAc (150 mL). This solution waswashed with water (3×100 mL), brine (100 mL) and dried (Na2SO4)., Removal of the solvent under reduced pressure gave a solid which was purified by filtration through a plug of silica gel (10% acetone/CH2C12 as eluant). The title compound was isolated as a very pale yellow crystalline solid (1.64 g, 80%). ? H NMR [400 MHz, (CD3)2S0] oe 7.85 (dd, J= 1.5, 0.6 Hz, 1 H), 7.66 (dd, J= 8.0, 1.7 Hz, 1 H), 7.59 (d, J- 8.0 Hz, I H), 4.46 (s,2 H), 3.05 (s, 3 H). LRMS (APCI) calcd for C9H8BrNO 226, 228 (MH), found 226, 228.

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, 6-Bromoisoindolin-1-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PETER MACCALLUM CANCER INSTITUTE; SPICER, Julie Ann; DENNY, William Alexander; MILLER, Christian Karl; O’CONNOR, Patrick David; HUTTUNEN, Kristiina; TRAPANI, Joseph A.; HILL, Geoff; ALEXANDER, Kylie; WO2014/28968; (2014); A1;,
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3416-57-7, name is 2-(2-Oxopropyl)isoindoline-1,3-dione, 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. 3416-57-7

To a mixture of N-acetonylphthalamide 3 (8.8 g, 43.3 mmol) and pyrrole (40 mL) was added TFA (3.2 mL, 43.3 mmol) in one portion. The reaction solution was stirred for 10 h at room temperature. The reaction was quenched by adding triethylamine (5 mL). The residual pyrrole was then removed by evaporation in vacuo. To the resulting brownish sticky oil, CH2Cl2 (150 mL) and 10% aqueous NaOH (100 mL) were added, before the organic layer was separated off and washed three times with 120 mL of water. The organic layer was dried over anhydrous MgSO4 and the solvent was removed invacuo to give a brownish sticky oil. The crude product was purifiedby column chromatography over silica gel (1:1 ethyl acetate: hexanesv/v) to give 6.17 g (44.7% yield) of 4 as a pale yellowish solid: 1H NMR (600 MHz, DMSO-d6) delta 10.39 (s, 2H), 7.80 (s, 4H), 6.60-6.59 (q, 2H, J = 2.4 Hz), 5.85-5.84 (q, 2H, J = 2.4 Hz), 5.79-5.78 (m, 2H), 4.07 (s, 2H), 1.57 (s, 3H); 13C NMR (150 MHz, DMSO-d6) delta 167.6, 135.0, 134.1, 131.5, 122.8, 117.1, 106.3, 104.4, 46.8, 40.5, 24.4. HRMS(ESI): m/z calcd for C19H17N3O2 [M – H]-: 318.1243; found 318.1249.

Statistics shows that 3416-57-7 is playing an increasingly important role. we look forward to future research findings about 2-(2-Oxopropyl)isoindoline-1,3-dione.

Reference:
Article; He, Ying-Chun; Ren, Zhen-Xing; Zhao, Xue-Feng; Zhang, Yong-Bin; Wang, Jun-Hong; Chao, Jian-Bin; Wang, Meng-Liang; Tetrahedron; vol. 75; 36; (2019);,
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Adding some certain compound to certain chemical reactions, such as: 3335-98-6, name is 1-Phenyloxindole, 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 3335-98-6. 3335-98-6

General procedure: A mixture of isatins (1, 1.0 mmol), indolin-2-ones (2, 1.0 mmol) and ZrCl4 (23 mg, 0.1 mmol) was heated in anhydrous ethanol (5 mL) under reflux. After the disappearance of the reactants (8-12 h, monitored by TLC), the mixture was slowly cooled to room temperature. The red solids precipitated and were collected by filtration, then washed by a small amount of anhydrous ethanol to deliver pure compounds 3.

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 1-Phenyloxindole.

Reference:
Article; Liu, Meilin; Qiu, Shaozhong; Ye, Yu; Yin, Guodong; Tetrahedron Letters; vol. 57; 52; (2016); p. 5856 – 5858;,
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2058-72-2, 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.

General procedure: A mixture of isatin(1.0 mmol), alpha-amino acid (1.0 mmol) and acrylamide (1.0 mmol) in 4.0 mL aqueous methanol (1:3) was heated in an oil bath to reflux temperature for 40 min to 7 hours. The resulting precipitates were collected by filtration and washed with cold methanol to give the analyticallypure products 4.

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 2058-72-2.

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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99365-40-9, A common compound: 99365-40-9, name is 6-Bromoindolin-2-one, belongs to indolines-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

General procedure: To the phenstatin-3-aldehyde/isocombretastatin-3-aldehyde(16a-b) (0.303 mmol/0.304 mmol) prepared in the above stepwas added corresponding substituted oxindoles (17a-h)(0.303 mmol) and catalytic amount of piperidine (1.0 ml) in ethanol.Heated the reaction mixture to reflux for 4 h at 85 C. The solidcompounds obtained in the reaction vessel were filtered and washed with ethanol for 4-5 times. After complete air drying thefinal compounds phenstatin/isocombretastatin-oxindole analogs(5a-h and 6a-h) were obtained as pure solids (yield 71-90%).

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

Reference:
Article; Kumar, G. Bharath; Nayak, V. Lakshma; Sayeed, Ibrahim Bin; Reddy, Vangala Santhosh; Shaik, Anver Basha; Mahesh, Rasala; Baig, Mirza Feroz; Shareef, Mohd Adil; Ravikumar; Kamal, Ahmed; Bioorganic and Medicinal Chemistry; vol. 24; 8; (2016); p. 1729 – 1740;,
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