Category: bromides-buliding-blocks

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. 141474-37-5, name is 2,4-Dibromo-6-fluoroaniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 2,4-Dibromo-6-fluoroaniline

General procedure: A mixture of 2-iodoaniline (0.20 mmol), phenyl isothiocyanate (0.22 mmol), DABCO (0.40 mmol, 2.0 equiv) and polystyrene-immobilized phenanthroline-Cu(I) catalyst 4 (20 mg, containing Cu 0.005 mmol) and toluene (1.0 mL) was stirred at 60 C for 8 h. After completion of the reaction as indicated by TLC, the mixture was cooled to room temperature and Et2O (5.0 mL) was added and the mixture stirred for 10 min to ensure product removal from catalyst. As supported catalyst 4 was precipitated to the bottom of the flask, the organic layer was decanted and the residue was washed with Et2O (2×5.0 mL). The combined organic layers were concentrated, and then the residue was purified by flash chromatography on silica gel to provide the corresponding pure product 7a in 95% yield.

The synthetic route of 141474-37-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yang, Jin; Li, Pinhua; Wang, Lei; Tetrahedron; vol. 67; 31; (2011); p. 5543 – 5549;,
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Synthetic Route of 337915-79-4, 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. 337915-79-4 name is 5-Bromo-N1-methylbenzene-1,2-diamine, 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 5 – bromo – N1- Methyl phenyl – 1, 2 – diamine (1.02 g, 5 . 07 mmol) and 2 – (4 – (trifluoromethyl) phenyl) acetic acid (2.01 mg, 9 . 85 mmol) is added to the toluene (25 ml) in, 120 C oil bath is heated under reflux reaction 42 h. The reaction cooling to room temperature, concentrated under reduced pressure, the residue added to in DCM (60 ml), HCl aqueous solution for sequentially (1.0 M, 20 ml), saturated NaHCO3Aqueous solution (20 ml) and saturated NaCl aqueous solution (20 ml) washing, anhydrous Na2SO4Drying, concentrated under reduced pressure, the crude product by silica gel column chromatography (eluent: PE/EtOAc (v/v)=2/1), to obtain the product as a yellow solid (500 mg, 27%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromo-N1-methylbenzene-1,2-diamine, and friends who are interested can also refer to it.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Zhong Xue; Wang Feng; Li Xuke; He Wei; Guan Mingyu; Liu Bing; Zhang Yingjun; Zheng Changchun; (105 pag.)CN108689942; (2018); A;,
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Adding a certain compound to certain chemical reactions, such as: 937046-98-5, name is 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-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 937046-98-5, SDS of cas: 937046-98-5

To a solution of compound 7-bromopyrrolo[2,1-fj[1,2,4]triazin-4-amine (1.5 g, 7.0 mmol) in DME (20 mL), the pinacol ester of 2-indeneboronic acid (1.5 eq.), 2M aq. Na2CO3 (4.0 eq.) were added and degassed with N2 for 15mm. Then Pd(dppf)C12.DCM (5 mol%) was added to the mixture and again degassed for 15 mm. The solution was heated in at 100 C for lh and then allowed to cool at RT. Then the mixture was diluted with 25 mL water and 25 mL EtOAc and extracted. Then the organic layer was washed with brine and dried over anhydrous sodium sulfate and concentrated. The crude gummy liquid was purified by column to afford 7- (1 H-inden-2-yl)pyrrolo [2,1 -fj [1,2,4] triazin-4-amine (970 mg, 57% yield).

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, 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MEDIVATION TECHNOLOGIES, INC.; RAI, Roopa; CHAKRAVARTY, Sarvajit; GREEN, Michael, John; PHAM, Son, Minh; PUJALA, Brahmam; AGARWAL, Anil, Kumar; NAYAK, Ajan, Kumar; KHARE, Sweta; GUGULOTH, Rambabu; RANDIVE, Nitin, Atmaram; WO2015/58084; (2015); A1;,
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These common heterocyclic compound, 399-94-0, name is 1-Bromo-2,5-difluorobenzene, 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. Safety of 1-Bromo-2,5-difluorobenzene

Example 3 3 -((2.5 -difluorophenyl)ethynyl)-5 -( 1 -(piperidin-4-yl)- 1 H-pyrazol-4-yl)- 1 H- pyrrolor2,3-b1pyridine Step 1) tert-butyl 4-(4-(3-((2.5-difluorophenyl ethvnyl -lH-pyrrolor2.3-b1pyridin-5-yl -lH- pyrazol- 1 -yPpiperidine- 1 -carboxylate To a microwave vial was added tert-butyl 4-(4-(3-ethynyl-lH-pyrrolo[2,3-b] pyridin-5-yl)-lH- pyrazol-l-yl)piperidine-l -carboxylate (0.1 g, 0.26 mmol), 2-bromo-l,4-difluorobenzene (58 mg, 0.26 mmol), Pd(PPh3)2Cl2 (9.0 mg, 0.013 mmol), Cul (2.0 mg, 0.013 mmol), Et3N (1 mL), and DMF (4 mL). The mixture was degassed and charged with nitrogen for three times. The vial was capped and then stirred and heated under microwave conditions at 120 C for 30 minutes. Then the mixture was cooled to rt, diluted with DCM (100 mL), and washed with brine (100 mL x 3). The separated organic phase was dried over anhydrous Na2S04 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (v/v) = 1/2) to give the title compound as a light yellow solid (0.14 g, 81%). MS (ESI, pos. ion) m/z: 504.2 (M+l); ‘HNMR: (400 Hz, DMSO-i): delta 1.43 (s, 9H), 1.84 (m, 2H), 2.05 (m, 2H), 2.95 (s, 2H), 4.06 (m, 2H), 4.38 (m, IH), 7.31 (m, IH), 7.38 (m, IH), 7.62 (m, IH), 7.98 (d, J=2.8 Hz, IH), 8.02 (s, IH), 8.19 (d, J=1.8 Hz, IH), 8.41 (s, IH), 8.62 (d, J=1.8 Hz, IH), 12.26 (s, IH).

The synthetic route of 1-Bromo-2,5-difluorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CALITOR SCIENCES, LLC; SUNSHINE LAKE PHARMA CO., LTD.; XI, Ning; LI, Xiaobo; ZHOU, Shiqing; WO2014/89280; (2014); A1;,
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Reference of 626-88-0, 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 626-88-0 as follows.

General procedure: 4-Bromomethylbiphenyl (402 mg, 1.63 mmol) and K2CO3(247 mg, 1.79 mmol) were added to a stirred solution of 237)(500 mg, 1.63 mmol) in DMF (5 mL), followed by stirring atroom temperature for 15 h. After the addition of water, themixture was extracted with AcOEt, washed with water andsaturated brine, and then dried over Na2SO4. The solventwas removed under reduced pressure. The residue obtainedwas purified by silica gel column chromatography to give 3j(790 mg, quant.) as a white solid.

According to the analysis of related databases, 626-88-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Morishita, Ko; Shoji, Yoshimichi; Fukui, Masaki; Ito, Yuma; Kitao, Tatsuya; Ozawa, Shin-ichiro; Hirono, Shuichi; Shirahase, Hiroaki; Chemical and Pharmaceutical Bulletin; vol. 66; 12; (2018); p. 1131 – 1152;,
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Related Products of 69321-60-4,Some common heterocyclic compound, 69321-60-4, name is 2,6-Dibromotoluene, molecular formula is C7H6Br2, 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.

3-Bromo-2-methylbenzonitrile. This compound was prepared in a manner similar to that described for 3-bromo-5-fluorobenzonitrile from commercially available 2,6-dibromotoluene (1.80 g, 7.20 mmol), DMF (11 mL), pyridine (1.1 mL), and copper (I) cyanide (0.52 g, 5.76 mmol). The crude product was purified by flash column chromatography (100 mL silica, hexane) to afford 50 mg (35%) of 3-bromo-2-methylbenzonitrile.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,6-Dibromotoluene, its application will become more common.

Reference:
Patent; Ligand Pharmaceuticals Incorporated; US5696130; (1997); A;,
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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. 418762-26-2, name is 4-Bromo-2-fluoro-5-methylaniline, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 4-Bromo-2-fluoro-5-methylaniline

a) N-(4-bromo-2-fluoro-5-methylphenyl)-2-{[(35)-l-(cyclopropylcarbonyl)-3- pyrrolidinyl]acetyl}hydrazinecarboxamideTo a round bottom flask was added triphosgene (2.57 mmol) and dichloromethane (20 mL) under nitrogen, and the solution was cooled to -78 C. In a separate vial, 4- bromo-2-fluoro-5-methylaniline (7.35 mmol) was dissolved in dichloromethane (20 mL) and Hunig’s base (18.4 mmol) was added. This solution was slowly added to the cooled solution and then the reaction was allowed to warm to room temperature. After 10 min, analysis by LCMS indicated desired intermediate formation. The reaction was cooled again to -78 C and 2-[(35)-l-(cyclopropylcarbonyl)-3-pyrrolidinyl]acetohydrazide (4.41 mmol) in dichloromethane (5 mL) was added slowly. The reaction was allowed to warm to room temperature and stirred for 20 min. Analysis by LCMS indicated desired product formation. The reaction was poured into a separatory funnel and partitioned with saturated aq sodium bicarbonate. The aqueous layer was extracted with dichloromethane (3x) and the combined organic layers were dried over Na2S04, filtered, and concentrated to an oil. The residue was purified by silica gel chromatography (0-15%isopropanol/ethyl acetate). The desired fractions were combined and concentrated to afford the title product as an oil (1.9 g, 59%). MS(ES)+ m/e 441.0, 442.9 [M+H]+.

According to the analysis of related databases, 418762-26-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE LLC; ADAMS, Nicholas, D.; AQUINO, Christopher, Joseph; CHAUDHARI, Amita, M.; GHERGUROVICH, Jonathan, M.; KIESOW, Terence, John; PARRISH, Cynthia, A.; REIF, Alexander, Joseph; WIGGALL, Kenneth; WO2011/103546; (2011); A1;,
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Some common heterocyclic compound, 1074-24-4, name is 1,4-Dibromo-2,5-dimethylbenzene, molecular formula is C8H8Br2, 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. SDS of cas: 1074-24-4

1, 4-dibromo-2,5-dimethylbenzene: 1H-1,2,4-triazole: potassium carbonate: copper oxide molar ratio of 2: 10: 30: 1A solution of CuO (0.0398 mg, 0.5 mmol), potassium carbonate (2.0731 g, 15 mmol), 1H-1,2,4-triazole (0.345 g, 0.5 mmol), and triethylamine Mg, 5 mmol), 1,4-dibromo-2,5-dimethylbenzene (0.3360 g, 1 mmol), 20 mL of DMF. Stirring was started at 100oC for 24 hours. After the completion of the reaction, the reaction solution was cooled to room temperature, filtered, and the filtrate was added with 100 mL of water. A large amount of precipitate was precipitated, and the filter cake was collected by suction filtration at a yield of 60percent. Elemental analysis (C12N6H12) Calcd. (percent): C, 59.99; H, 5.03; N, 34.98. Found: C, 60.02; H, 5.05; N, 35.05;1,4-dibromo-2,5-dimethylbenzene 1H-1,2,4-triazole.In the present invention, the molar ratio of 1,4-dibromo-2,5-dimethylbenzene: 1H-1,2,4-triazole: potassium carbonate:2: 10: 30: 1; reaction temperature 80-200 , reaction time 12-120 hours. The organic compound was prepared by heating 1,4-dibromo-2,5-dimethylbenzene and 1H-1,2,4-triazole in a one-pot process. 1- (2,5- Dimethyl-4- (1H-1,2,4-Triazol-1-yl) phenyl) -1H-1,2,4-triazole (L).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1074-24-4, its application will become more common.

Reference:
Patent; Tianjin Normal University; Wang, Ying; (12 pag.)CN105418659; (2016); A;,
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656-64-4, name is 3-Bromo-4-fluoroaniline, 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. Formula: C6H5BrFN

The compound N-hydroxy-4-((3-methoxypropyl)amino)-1,2,5-oxadiazol-3-carbamimidinyl chloride (2.5 g, 10.64 mmol) was added to water. (14 ml) was heated to 60 C, 3-bromo-4-fluoroaniline (2.06 g, 11 mmol) was added, stirred for 10 minutes, then sodium bicarbonate (1.26 g, 15 mmol) was added at 60 C for 30 minutes until the reaction was complete. Extract with ethyl acetate, wash the organic phase with water, and wash with saturated brine.Drying the organic phase with anhydrous sodium sulfate,Concentrated under vacuumN-(3-Bromo-4-fluorophenyl)-N’-hydroxy-4-3-methoxypropyl)amino)-1,2,5-oxadiazole-3-carboximidamide 6e (3.9 g, 94.0%)

The synthetic route of 656-64-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangsu Hansoh Pharmaceutical Group Co., LTD (CN); Shanghai Hansoh Biomedical Co.,Ltd (CN); WU, SHENG HUA; GUO, FENG YING; LI, KAI LONG; HUANG, ZHI QIANG; BAO, RUDI; (94 pag.)TW2018/23219; (2018); A;,
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Electric Literature of 28342-75-8, 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. 28342-75-8, name is 1,5-Dibromo-2,4-difluorobenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

1,5-dibromo-2,4-difluorobenzene (6.4 mmol) was dissolved in ACN (12 mL), and wasadded TEA (2.6 mL), TMS-acetylene (1.6 equiv), CuT (0.16 equiv), and Pd(PPh3)2Cp2 (0.1 equiv) sequentially. The mixture was stirred at 65°C for 6 hours. The mixture was filtered, evaporated and purified on a flash column. The collected fractions were dried and treated with 1 M TBAF in THF for two hours. The solvent was removed on a rotovap. The residue was added EtOAc and water. The organic layer was dried, evaporated and purified on a column.

The synthetic route of 1,5-Dibromo-2,4-difluorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CELLCEUTIX CORPORATION; FAN, Xiaodong; XU, Yongjiang; LIU, Dahui; COSTANZO, Michael J.; WO2014/93225; (2014); A2;,
Bromide – Wikipedia,
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