Tag: M.W=200-300

Related Products of 167355-41-1,Some common heterocyclic compound, 167355-41-1, name is 6-Bromo-1,2,3,4-tetrahydronaphthalen-2-amine, molecular formula is C10H12BrN, 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.

Di-tert-butyl dicarbonate (1.030 g, 4.719 mmol) was added to a stirred RT solution of 6-bromo-1,2,3,4-tetrahydro-naphthalen-2-ylamine (0.970 g, 4.290 mmol) in CH2Cl2 (100 mL). TEA (0.897 mL, 6.435 mmol) was added to the reaction and the mixture was stirred at RT until HPLC analysis showed complete consumption of starting material. The reaction was diluted with CH2Cl2, washed with saturated aqueous NaHCO3, dried over MgSO4 and concentrated in vacuo to afford the crude material. The crude was purified by flash column chromatography to yield the title compound. MS (APCI pos) 269 (M-t-Bu).

The synthetic route of 167355-41-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Amgen Inc.; Array Biopharma, Inc.; US2005/234044; (2005); A1;,
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1435-54-7, name is 1,3-Dibromo-2-fluorobenzene, belongs to bromides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Quality Control of 1,3-Dibromo-2-fluorobenzene

General procedure: Scheme 4-1: In Step 1 the appropriately substituted dibromo species is coupled with an appropriate boronic acid as known in the art to form a mixture of biaryl and triaryl products from which the desired biaryl compound is isolated. In Step 2 the appropriately substituted biaryl species is converted to the Grignard reagent with activated magnesium. In Step 3 the appropriately substituted aldehyde is treated with the previously prepared Grignard reagent to form an alcohol. In Step 4 the appropriately substituted alcohol is converted to a bromide as known in the art with carbon tetrabromide and triphenyl phosphine. In Step 5 the appropriately substituted bromide is converted to the Grignard reagent with activated magnesium.

The synthetic route of 1435-54-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; PHADKE, Avinash, S.; DESHPANDE, Milind; AGARWAL, Atul; CHEN, Dawei; GADHACHANDA, Venkat, Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; GREENLEE, William; (340 pag.)WO2017/35415; (2017); A1;,
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Adding a certain compound to certain chemical reactions, such as: 771-14-2, name is 2-Bromonaphthalen-1-amine, belongs to bromides-buliding-blocks 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 771-14-2, Application In Synthesis of 2-Bromonaphthalen-1-amine

General procedure: To a solution of 2-bromoaniline (1.0 equiv.) and N,N-diisopropylethylamine (2.4 equiv.) in toluene was added cis-1,4-dichlorobut-2-ene (1.8 equiv.). The mixture was stirred at reflux until complete consumption monitored by TLC. The reaction was cooled to room temperature, diluted with water, and extracted with EtOAc. The combined organic layers were washed with saturated NaCl solution and dried over Na 2 SO 4 . The solvents were removed under reduced pressure, purified by flash chromatography to give the pure or crude desired product 3. The product 3 was dissolved in anhydrous THF, then was cooled to -78 oC, n-BuLi (1.2 equiv., 2.5 mol/L in n-hexane) was added dropwise to the mixture and keep temperature no more than -50 oC, the mixture was stirred for 30 minutes, (COOR3) 2 (1.0-1.2 equiv.) in THF was added dropwise at -78 oC and stirred at -78 oC for 2 h. The reaction was warmed to room temperature slowly, then quenched with saturated NH 4 Cl solution, and extracted with EtOAc. The combined organic layers were washed with saturated NaCl solution and dried over Na 2 SO 4 . The solvents were removed under reduced pressure, purified by flash chromatography to give the desired product 1.

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-Bromonaphthalen-1-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Du, Hong-Jin; Lin, Chao; Wen, Xiaoan; Xu, Qing-Long; Tetrahedron; vol. 74; 52; (2018); p. 7480 – 7484;,
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Related Products of 69038-76-2,Some common heterocyclic compound, 69038-76-2, name is 4-Bromo-N1-methylbenzene-1,2-diamine, molecular formula is C7H9BrN2, 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 solution of 4-bromo-N?-methylbenzene-1,2-diamine (1.7 g, 8 mmol) in triethyl orthoformate (10 mL) was added PTSA?H20 (152 mg, 0.8 mmol). The mixture was stirred at 85 C for 2 h, poured into H20 (50 mL) and extracted with EA (40 mL x 2). The organic layers were dried over anhydrous Na2SO4, filtered, concentrated in vacuo, and purified by silica gel column chromatography (PE/EA = 50/1 to 10/1) to afford 5-bromo-1-methyl-1H-benzo[djimidazole (1.5 g, 89 %) as a yellow solid. LC-MS mlz: 211.1 [M+Hf?. tR= 1.90 mm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-N1-methylbenzene-1,2-diamine, its application will become more common.

Reference:
Patent; LYSOSOMAL THERAPEUTICS INC.; SKERLJ, Renato, T.; BOURQUE, Elyse Marie Josee; LANSBURY, Peter, T.; GOOD, Andrew, C.; (391 pag.)WO2017/176960; (2017); A1;,
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Reference of 112734-22-2, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 112734-22-2, name is (4-Bromo-2-fluorophenyl)methanamine belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 1 : (4-Bromo-2-fluorophenyl)methanamine (924 mg, 4.53 mmol) was dissolved in pyridine and ethane sulfonyl chloride (0.82 mL, 8.60 mmol) was added to the solution at 0 C. The mixture was stirred for 1 h at 0 C. Then, the mixture was quenched with 1 N HCI and extracted with ethyl acetate. Drying over magnesium sulfate and evaporation of the ethyl acetate and purified by column chromatography gave N-(4-bromo-2-fluorobenzyl)- ethanesulfonamide in pure form (1 .06 g, 79 %).

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, (4-Bromo-2-fluorophenyl)methanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GRUeNENTHAL GMBH; FRANK, Robert; BAHRENBERG, Gregor; CHRISTOPH, Thomas; LESCH, Bernhard; LEE, Jeewoo; WO2013/45447; (2013); A1;,
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Application of 608-30-0, A common heterocyclic compound, 608-30-0, name is 2,6-Dibromoaniline, molecular formula is C6H5Br2N, 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.

(1) Adding 1 mole of 2,6-dibromoaniline to a four-necked flask,Adding 50% sulfuric acid to the flask, stirring was started, and a 15% aqueous solution of sodium nitrite was added dropwise at a temperature of 0-5 C, and the dropping time was 2 hours.After the dropwise addition is kept for 1 hour, 2,6-dibromoaniline is subjected to diazotization reaction at 0 to 5 C under acidic conditions, and the reaction is completed to obtain a dibromoaniline diazonium salt aqueous solution;The molar ratio of 2,6-dibromoaniline to sodium nitrite is 1:1.05, and the molar ratio of sodium nitrite to sulfuric acid is 1:4;(2) adding hypophosphorous acid to the flask in the dibromoaniline diazonium salt aqueous solution prepared in the step (1), then raising the temperature to 70-80 C, and maintaining the reaction for 3 hours to obtain a mixed solution containing m-dibromobenzene. ; the molar ratio of hypophosphorous acid to 2,6-dibromoaniline is 1.3:1;(3) The mixture obtained in the step (2) is allowed to stand for 30 minutes to be layered, and then the inorganic phase and the organic phase are separated, the organic phase is washed with water, and the inorganic phase and the organic phase are separated by standing. The organic phase can be distilled under reduced pressure to obtain m-dibromobenzene; the calculated yield is over 81%, and the detection purity is over 98%.

The synthetic route of 608-30-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shandong Tianyi Chemical Co., Ltd.; Tang Xingsan; Xing Xiaohua; Zhang Ming; (6 pag.)CN110078587; (2019); A;,
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Related Products of 502496-36-8,Some common heterocyclic compound, 502496-36-8, name is 3-Bromo-5-fluoro-2-methylaniline, molecular formula is C7H7BrFN, 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.

[00404] 3-Bromo-5-fluoro-2-methyl-aniline (725 mg, 3.55 mmol), bis(pinacolato)diboron(1 .08 g, 4.26 mmol) and potassium acetate (1 .05 mg, 10.7 mmol) were mixed in 1 ,4-dioxane (35 mL) and nitrogen gas was blown through for 5 minutes. 1,1-Bis(diphenyl-phosphino)ferrocene- palladium(1,1)dichloride DCM adduct (174 mg, 0.21 mmol) was added and the mixture was heated under ref lux conditions for 4 hours. The reaction was allowed to cool – excess dioxanewas removed and the residue was diluted with EtOAc and filtered through celite. The organic solution was concentrated. The crude material was purified by column chromatography (24g silica) with a gradient 0 – 50% EtOAc in hexanes to give 5-fluoro-2-methyl-3-(4,4,5,5- tetramethyl-1 ,3,2-dioxaborolan-2-yl)aniline (0.761 g, 2.79 mmol, 78.5%).[00405] 1H NMR (DMSO-d6): O 6.91 (dd, J= 2.7 and 9.0 Hz, 1H), 6.50 (dd, J= 2.6 and10.0 Hz, 1H), 3.88 (bs, 2H), 2.34 (5, 3H), 1.36 (5, 12H).

The synthetic route of 502496-36-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; GOLDBERG, Kristin; HAMILTON, Niall; JONES, Stuart; JORDAN, Allan; LYONS, Amanda; NEWTON, Rebecca; OGILVIE, Donald; WASZKOWYCZ, Bohdan; WO2015/79251; (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 1435-52-5 as follows. Recommanded Product: 1,4-Dibromo-2-fluorobenzene

To a stirred solution of 1,4-dibromo-2-fluorobenzene (100 g, 395.2 mmol) in ethylene glycol(510 mL), NMP (50 mL) was added at rt under N2 atmosphere. Then tBuOK (155.2 g,1383.0 mmol) was added slowly over 10 mm at 10 C. The reaction mixture was heated at100 C for 12 h. The completion of the reaction was monitored by TLC. The reaction mixture was cooled to rt and diluted with water (200 mL) and stirred for 15 mm at rt. The resulting solid was filtered and washed with ethylene glycol (2 x 30 mL). Water (2200 mL) was added to the filtrate, the solution was cooled to 15 C and stirred for I h. The resulting precipitate was filtered and washed with water (2 x 100 mL), pet ether (2 x 100 mL) and dried. It was further dried with the addition of toluene and its evalportaion (3 x 200 mL). It was then use in the next step without further purification. Yield: 77.5% (90 g, pale brown solid). 1H NMR (400 MHz, CDCI3): 6 7.41 (d, J = 8.4 Hz, I H), 7.06 (d, J = 2.0 Hz, I H), 7.02 (dd, J = 8.4, 2.4 Hz, IH), 4.14 (t, J = 4.4 Hz, 2H), 4.03-4.00 (m, 2H), 2.36 (t, J = 6.4 Hz,IH).

According to the analysis of related databases, 1435-52-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASCENEURON S. A.; QUATTROPANI, Anna; KULKARNI, Santosh, S.; GIRI, Awadut, Gajendra; (280 pag.)WO2017/144633; (2017); A1;,
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Reference of 179737-33-8, 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 179737-33-8 as follows.

In an Ar atmosphere, 20.00 g (73.56 mmol) of 2,3-dibromo-1,4-difluorobenzene, 12.30 g (1.1 equiv, 80.9 mmol) of 2-methoxyphenylboronic acid, 80.92 g (3 equiv, 220.7 mmol) of K2CO3, 4.25 g (0.05 equiv, 3.7 mmol) of Pd(PPh3)4, and 515 mL of a mixed solution of toluene/EtOH/H2O (4/2/1) were sequentially added to a 1,000-mL three-neck flask, and heated and stirred at a temperature of 80 C. for 5 hours. After cooling to room temperature, the reaction solution was extracted therefrom by using toluene. A water layer was removed therefrom, and an organic layer was cleaned by using saturated saline and dried by using MgSO4. MgSO4 was filtered and separated and the organic layer was concentrated. A crude product obtained therefrom was purified by silica gel column chromatography (mixed solvent of hexane and toluene was used in a development layer) to obtain Intermediate IM-1 (16.94 g, yield of 77%). (0394) Intermediate IM-1 was identified by observing the mass number m/z=299 as the molecular ion peak through FAB-MS.

According to the analysis of related databases, 179737-33-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Samsung Display Co., Ltd.; Uno, Takuya; (153 pag.)US2019/389877; (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. 142808-15-9, name is 4-Bromo-2-fluorobenzotrifluoride, A new synthetic method of this compound is introduced below., name: 4-Bromo-2-fluorobenzotrifluoride

Into a 10000-mL 4-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed tetrahydrofuran (5000 mL), NH(i-Pr)2 (249 g, 1.20 equiv). This was followed by the addition of n-BuLi (905 mL, 1.10 equiv) dropwise with stirring in 30 min at -70C. The resulting solution was stirred for 0.5 hr at -30C. To this was added 4-bromo-2-fluoro- l-(trifluoromethyl)benzene (500 g, 2.06 mol, 1.00 equiv) dropwise with stirring at -78C in 2 hr. The resulting solution was stirred for 2 hr at -78C. The reaction was then poured into 1000 g of C02(s) at -70C. The pH value of the solution was adjusted to 3 with hydrogen chloride (2N) (1.5 mol/L). The resulting solution was extracted with 3×2000 mL of ethyl acetate and the organic layers combined and dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 301 g (50%) of 6-bromo-2-fluoro-3-(trifluoromethyl)benzoic acid as a white solid.

The synthetic route of 142808-15-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MANDAL, Mihir; TANG, Haifeng; XIAO, Li; SU, Jing; LI, Guoqing; YANG, Shu-Wei; PAN, Weidong; TANG, Haiqun; DEJESUS, Reynalda; HICKS, Jacqueline; LOMBARDO, Matthew; CHU, Hong; HAGMANN, William; PASTERNAK, Alex; GU, Xin; JIANG, Jinlong; DONG, Shuzhi; DING, Fa-Xiang; LONDON, Clare; BISWAS, Dipshikha; YOUNG, Katherine; HUNTER, David, N.; ZHAO, Zhiqiang; YANG, Dexi; WO2015/112441; (2015); A1;,
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