Category: 6326-79-0

Synthetic Route of 6326-79-0, These common heterocyclic compound, 6326-79-0, name is 6-Bromoisatin, 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.

Bis(2-methoxyethyl)aminosulfur trifluoride (deoxo-fluor, 44.25 mL, 22.12 mmol, 50% solution in THF) was added dropwise over 30 min to a suspension of 6-bromoisatin (2.0 g, 8.75 mmol) in DCM (90 mL) at rt with stirring. After 24 h the reaction was cautiously quenched with saturated sodium hydrogen carbonate solution (40 mL) solution at 0 C. The layers were separated and the organics extracts dried (hydrophobic frit/phase separator) and concentrated under reduced pressure. The crude material was purified by silica gel column chromatography eluting with 20% EtOAc in iso-hexane to afford the subtitled compound as an orange solid (1.63 g, 74%). 1H NMR (400 MHz, CH3OH-d4): delta 7.50-7.46 (m, 1H), 7.36 (dd, 1H), 7.18 (d, 1H), (one exchangeable not observed).

The synthetic route of 6326-79-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AstraZeneca AB; Lonn, Hans Roland; Connolly, Stephen; Swallow, Steven; Karlsson, Staffan PO; Aurell, Carl-Johan; Ponten, John Fritiof; Doyle, Kevin James; Van de Poel, Amanda Jane; Jones, Graham Peter; Watson, David Wyn; MacRitchie, Jaqueline Anne; Palmer, Nicholas John; (50 pag.)US9522894; (2016); B2;,
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Application of 6326-79-0,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.

To a stirred solution of sodium hydroxide (0.48 g, 12.0 mmol) in water (8 ml) was added 6-bromoisatin (2.5 g, 11.0 mmol). The reaction mixture was gently heated until it became dark red. This dark-red solution was cooled to 0 C and mixed with a solution of sodium nitrite (0.76 g, 11 mmol) in water (3 ml) at 0 C. The combined solution was then added to a rapidly stirred solution of sulphuric acid (1.1 ml, 22.0 mmol) in water (42 ml) via dropping funnel at 0 C. The rate of addition was maintained such that the temperature of reaction mixture should not rise above 5 C. After completion of addition, the brownish- yellow solution was stirred for 15 minutes. Then a cold solution of stannous chloride dihydrate (6 g, 26.5 mmol) in concentrated hydrochloric acid (10 ml) was added from a dropping funnel to the stirred solution of the diazo-compound. The mixture was stirred for another 1 hour after the addition was complete. The crude product, a yellow to brown paste, was collected on a Buckner funnel (1.75 g, 65%) and used for the subsequent step directly without further purification. LCMS: m/z = 239.16 [M-l], 241.20 [M+l].

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

Reference:
Patent; CONSTELLATION PHARMCEUTICALS, INC.; WILSON, Jonathan, E.; LEVELL, Julian, R.; (152 pag.)WO2019/161157; (2019); 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. 6326-79-0, name is 6-Bromoisatin, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H4BrNO2

The 1.15g (5mmol) 6- bromo-isatin was dissolved in 10mL DMF,1.03 g (7.5 mmol) of potassium carbonate was added with stirring.Then, 0.804 g (6.25 mmol) of dimethyl sulfate was added dropwise, and the mixture was reacted at room temperature for 4 hours, and the mixture was poured into 100 mL of ice water.The extract was extracted with ethyl acetate (60 mL×3), and the organic layer was evaporated.After concentrated to dryness, it was purified by silica gel column chromatography ( petroleum ether: ethyl acetate = 20:3)0.753 g of a red solid was obtained in a yield of 63%.

The synthetic route of 6326-79-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shandong University; Li Xun; Yu Haipeng; Zheng Yongtang; Huang Xusheng; (15 pag.)CN110183372; (2019); A;,
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Adding a certain compound to certain chemical reactions, such as: 6326-79-0, name is 6-Bromoisatin, 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 6326-79-0, Computed Properties of C8H4BrNO2

To R27 (25.0 g, 111 mmol) in acetonitrile (750 mL) is added MeI (15 mL, 241 mmol) and K2CO3 (60.0 g, 434 mmol) and the reaction mixture is stirred at 60 C. for 2 h. The reaction mixture is filtered and concentrated. Water and ethyl acetate are added to the residue. The organic layer is extracted twice with water, dried over MgSO4 and concentrated. Yield 56%, m/z 240/242 [M+H]+, rt 0.48 min, LC-MS Method X001-004.

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

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ANDERSKEWITZ, Ralf; BINDER, Florian; GRAUERT, Matthias; GRUNDL, Marc; HAEBEL, Peter Wilhelm; OOST, Thorsten; PAUTSCH, Alexander; PETERS, Stefan; VINTONYAK, Viktor; US2014/275025; (2014); A1;,
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Synthetic Route of 6326-79-0, 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. 6326-79-0 name is 6-Bromoisatin, 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.

The mixture of IX-1 (6.5 g, 28.7 mmol), malonic acid (3.3 g, 31.7 mmol), NaOAc (2.95 g, 36 mmol) in AcOH (60 mL) were stirred at rt. After 6 hrs, NaOAc (2.95 g, 36 mmol) was added additional, then refluxed overnight. After cooling, the mixture was filtered and the filtrate was washed with water and EtOAc, then dried under reduced pressure to afford IX-2 (5 g, yield 66%) as a brown oil, which was used for next step directly.

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

Reference:
Patent; Buckman, Brad Owen; Nicholas, John Beamond; Emayan, Kumaraswamy; Seiwert, Scott D.; US2014/200215; (2014); 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. 6326-79-0, name is 6-Bromoisatin, This compound has unique chemical properties. The synthetic route is as follows., name: 6-Bromoisatin

To R7 (25.0 g, 111 mmol) in acetonitrile (750 mL) is added MeI (15 mL, 241 mmol) and K2CO3 (60.0 g, 434 mmol) and the reaction mixture is stirred at 60 C. for 2 h. The reaction mixture is filtered and concentrated. Water and ethyl acetate are added to the residue. The organic layer is extracted twice with water, dried over MgSO4 and concentrated. Yield 56%, m/z 240/242 [M+H]+, rt 0.48 min, LC-MS Method X001-004.

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 6326-79-0.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GRAUERT, Matthias; ANDERSKEWITZ, Ralf; GRUNDL, Marc; OOST, Thorsten; PAUTSCH, Alexander; PETERS, Stefan; US2014/275155; (2014); A1;,
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Electric Literature of 6326-79-0, 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. 6326-79-0, name is 6-Bromoisatin, This compound has unique chemical properties. The synthetic route is as follows.

To R7 (25.0 g, 111 mmol) in acetonitrile (750 mL) is added MeI (15 mL, 241 mmol) and K2CO3 (60.0 g, 434 mmol) and the reaction mixture is stirred at 60 C. for 2 h. The reaction mixture is filtered and concentrated. Water and ethyl acetate are added to the residue. The organic layer is extracted twice with water, dried over MgSO4 and concentrated. Yield 56%, m/z 240/242 [M+H]+, rt 0.48 min, LC-MS Method X001-004.

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

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GRAUERT, Matthias; ANDERSKEWITZ, Ralf; GRUNDL, Marc; OOST, Thorsten; PAUTSCH, Alexander; PETERS, Stefan; US2014/275155; (2014); A1;,
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Adding a certain compound to certain chemical reactions, such as: 6326-79-0, name is 6-Bromoisatin, 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 6326-79-0, Application In Synthesis of 6-Bromoisatin

To R27 (25.0 g, 111 mmol) in acetonitrile (750 mL) is added MeI (15 mL, 241 mmol) and K2CO3 (60.0 g, 434 mmol) and the reaction mixture is stirred at 60 C. for 2 h. The reaction mixture is filtered and concentrated. Water and ethyl acetate are added to the residue. The organic layer is extracted twice with water, dried over MgSO4 and concentrated. Yield 56%, m/z 240/242 [M+H]+, rt 0.48 min, LC-MS Method X001-004.

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

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ANDERSKEWITZ, Ralf; BINDER, Florian; GRAUERT, Matthias; GRUNDL, Marc; HAEBEL, Peter Wilhelm; OOST, Thorsten; PAUTSCH, Alexander; PETERS, Stefan; VINTONYAK, Viktor; US2014/275025; (2014); 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. 6326-79-0, name is 6-Bromoisatin, A new synthetic method of this compound is introduced below., category: indolines-derivatives

The conversion of substituted isatins to substituted Indazole-3- carboxylic acids is essentially the same methods as described by Snyder, H. R. et al. Thus, the substituted isatin (17-1) was suspended in IN NaOH and was heated at 50C for 30 min. The burgundy solution was allowed to cool to room temperature and was maintained for an additional one hour. The reaction mixture was cooled to 0 C and was treated with a solution of NaN02 (22 mmol) in water. This solution was added through a pipet submerged below the surface of H2S04 in water at 0c in 15 min. The reaction was maintained for an additional 30 min. A cold solution of Tin(II) chloride in con. HC1 was added to the reaction mixture over 10 min and the reaction mixture was stirred at the same temperature for an additional 2h. The solid filtered and washed with water several times and dried in vacuo to give quantitative mass balance of the product (17-2) with 80% NMR purity.

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; FENG, Yangbo; CHEN, Yen Ting; SESSIONS, Hampton; MISHRA, Jitendra K.; CHOWDHURY, Sarwat; YIN, Yan; LOGRASSO, Philip; LUO, Jun-Li; BANNISTER, Thomas; SCHROETER, Thomas; WO2011/50245; (2011); A1;,
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Adding a certain compound to certain chemical reactions, such as: 6326-79-0, name is 6-Bromoisatin, 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 6326-79-0, SDS of cas: 6326-79-0

To a solution of 3a (150 mg, 0.66 mmol) in dry acetone (30 mL) was added Na2CO3 (anh. ) (1.0 g) and dimethylsulfate (0.8 mL) under Ar and the reaction mixture was heated at 60 C for 20 h. Then, the mixture was filtered and the filtrate was carefully evaporated using a high vacuum pump (under 40 C). The solid residue was submitted to flash chromatography with CH2C12 to afford lla (140 mg, 0.58 mmol, 85%) (see Scheme 2 in Fig. 2B).

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:
Patent; THE ROCKEFELLER UNIVERSITY; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; WO2005/41954; (2005); A1;,
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