Author: Jessica.F

73918-56-6, name is 2-(4-Bromophenyl)ethanamine, 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. Patent; INDIANA UNIVERSITY RESEARCH AND TECHNOLOGY CORPORATION; ASSEMBLY BIOSCIENCES, INC.; TURNER, William W.; ARNOLD, Lee Daniel; MAAG, Hans; ZLOTNICK, Adam; WO2015/138895; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 10269-01-9, The chemical industry reduces the impact on the environment during synthesis 10269-01-9, name is (3-Bromophenyl)methanamine, I believe this compound will play a more active role in future production and life.

(4?-(Trifluoromethyl)biphenyl-3-yl)methanamine. A 1 00-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with (3- bromophenyl)methanamine (570 mg, 3.0 mmol), 4-(trifluoromethyl)phenylboronic acid (558 mg, 3.0 mmol), Pd(PPh3)4 (173 mg, 0.15 mmol), K3P04 (1.91 g, 9.0 mmol), DME (30 mL) and H20 (6 mL). The system was subject to 3 cycles of vacuum/argon flush and heated at reflux for overnight. The mixture was cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica-gel column chromatography eluting with 1:20 MeOH/CH2C12 to afford the title compound (640 mg, 85%) as brown solid. MS-ESI: [M+H] 252.1.

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, (3-Bromophenyl)methanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BROTHERTON-PLEISS, Christine E.; CHEN, Huifen; CHEN, Shaoqing; CHEN, Zhi; ERICKSON, Shawn David; ESTRADA, Anthony; KIM, Kyungjin; LI, Hongju; LOVEY, Allen John; LYSSIKATOS, Joseph P.; QIAN, Yimin; SO, Sung-Sau; WOVKULICH, Peter Michael; YI, Lin; WO2014/49047; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 51437-00-4, 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 51437-00-4 as follows.

To a solution of diisopropylamine (1.77g, 17.5 mmol, 1.1 eq) in THF (20 mL) was added n-BuLi (7.3 mL, 2.4 M in THF, 17.5 mmol, 1.1 eq) at -78C under N2. The mixture was stirred at -78C for lh, then a solution of 4-bromo-l-fluoro-2 -methyl-benzene (3 g, 15.8 mmol, 1.0 eq ) in THF (20 mL) was added dropwise. The reaction was stirred a further 2h at -78C then C02 gas was bubbled into the mixture for 30 min. The reaction was quenched by addition of water and acidified to pH 3 by addition of 1M HCl. The aqueous layer was extracted with EtOAc and the combined organic extracts were washed with brine, dried (Na2S04), filtered and evaporated in vacuo. The residue obtained was purified by chromatography to give the title compound as a white solid (697 mg, 21 %).LC-MS : m/z 230.9, 232.9 [M-H]” HNMR (400 MHz, DMSO-d6) ? 7.94 – 7.59 (m, 2H), 2.26 (s, 3H)

According to the analysis of related databases, 51437-00-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; FOVEA PHARMACEUTICALS; FEUTRILL, John; LERICHE, Caroline; MIDDLEMISS, David; WO2013/37705; (2013); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 58534-95-5, 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. 58534-95-5 name is 3-Bromo-2-fluoroaniline, 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.

To an ice cold solution of (2S,4R)-l-(tert-butoxycarbonyl)-4-fluoropyrrolidine-2- carboxylic acid (1 mmol) in 5 mL of CH2CI2, l-chloro-N,N,2-trimethyl-l-propenylamine 1.1 mmol) was added drop-wise with stirring. The stirring was continued for 3 hours, at same temperature. Then solid 3-bromo-2-fluoroaniline (1.1 mmol was added, followed by 3 mmol of Hiinig’s base. The cooling bath was removed and the reaction mixture was stirred overnight at RT. The solvent was co-evaporated with MeOH (1 mL). The residue was then purified by ISCO (eluent: 0-.5 % MeOH in CH2CI2) to afford the title compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Bromo-2-fluoroaniline, and friends who are interested can also refer to it.

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; (447 pag.)WO2017/35408; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 21865-50-9, name is 6-Bromo-2,3,4,9-tetrahydro-1H-carbazole, A new synthetic method of this compound is introduced below., Safety of 6-Bromo-2,3,4,9-tetrahydro-1H-carbazole

To a suspension of 39 (0.75 g, 3.0 mmol) in acetic acid (3 ml) is added acetyl chloride (0.21 ml, 3.0 mmol). The mixture is heated to reflux, resulting in a clear solution. After 2 hours, the reaction solution is cooled to room temperature (rt). A solid is precipitated out. The solid 48 is filtered and washed with hexanes (2 x), 0.24 g, 27%

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; PTC THERAPEUTICS, INC.; WO2006/58088; (2006); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 4549-33-1, 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. 4549-33-1, name is 1,9-Dibromononane, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of SA (15 mg, 0.06 mmol) in DMF (1 mL, freshly distilled from CaH2), was added K2CO3 (25 mg, 0.18 mmol), followed by the addition of dibromoalkane (0.24 mmol). The obtained mixture was then stirred under N2 atmosphere at 50 C for 12 h. Afterwards, the reaction mixture was cooled to room temperature and quenched by brine (5 mL). The mixture was then extracted with DCM(5 mL x 3), washed successively with brine (10 mL x 3) and water (10 mL x 3), dried over Na2SO4,filtered, and concentrated in vacuo. The residue was purified by silica gel CC (EtOAc/PE ranged from 5:95 to 10:90 depending on the TLC analysis) to yield 15-20.

The chemical industry reduces the impact on the environment during synthesis 1,9-Dibromononane. I believe this compound will play a more active role in future production and life.

Reference:
Article; Zhang, Jun; Ling, Wei; Yang, Zhiqiang; Liang, Yan; Zhang, Linyan; Guo, Can; Wang, Kailing; Zhong, Balian; Xu, Shihai; Xu, Ying; Marine Drugs; vol. 17; 2; (2019);,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 67567-26-4,Some common heterocyclic compound, 67567-26-4, name is 4-Bromo-2,6-difluoroaniline, molecular formula is C6H4BrF2N, 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 1-tert-butoxycarbonyl-4-methyl-piperidine-4-carboxylic acid (240 mg, 0.99 mmol, 1.0 eq.) in CH2Cl2 (8.0 mL) was added pyridine (320 mg, 0.32 mL, 3.9 mmol, 4.0 eq.), (COCl)2 (130 mg, 0.088 mL, 0.99 mmol, 1.0 eq.) followed by 2 drops of DMF. After 1 h at room temperature, 4-bromo-2,6-difluoro-aniline (210 mg, 0.99 mmol, 1.0 eq.) was added and the mixture was stirred at room temperature overnight, after which CH2Cl2 was added and washed with water and brine. The organic layers were dried, evaporated and purified over silica gel with ethyl acetate in hexanes (5 to 50% gradient) to give tert-butyl 4-[(4-bromo-2,6-difluoro- phenyl)carbamoyl]-4-methyl-piperidine-1-carboxylate (350 mg, 82%). 1H NMR (CDCl3) d: 7.43 (s, 1H), 7.11 (d, J= 6.6 Hz, 2H), 3.65 – 3.81 (m, 2H), 3.14 – 3.22 (m, 2H), 2.09 (d, J= 13.9 Hz, 2H), 1.46 – 1.52 (m, 2H), 1.45 (s, 9H), 1.32 (s, 3H).

The synthetic route of 67567-26-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PTC THERAPEUTICS, INC.; ZHANG, Nanjing; BABU, Suresh; BARRAZA, Scott J.; BHATTACHARYYA, Anuradha; CHEN, Guangming; KARP, Gary Mitchell; KASSICK, Andrew J.; MAZZOTTI, Anthony R.; MOON, Young-Choon; NARASIMHAN, Jana; SYDORENKO, Nadiya; TURPOFF, Anthony; WOLL, Matthew, G.; YAN, Wuming; (0 pag.)WO2020/5877; (2020); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. category: bromides-buliding-blocks

The compound 4-amino-N-hydroxy-1,2,5-oxadiazol-3-carboxamidine Int-1a (20 g, 123.4 mmol, prepared by the method disclosed in the patent application “WO2010005958”) is dissolved in acetic acid Ethyl ester (100mL)And water (100mL),Add 3-bromo-4-fluoroaniline (23.2 g, 123.4 mmol),Sodium bicarbonate (15.5 g, 185.1 mmol),Heat to 60 C, react for 3 hours,The mixture was cooled and EtOAc (EtOAc m.The title compound Int-1b (38 g, 120.9 mmol) was obtained in a yield of 98%.

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

Reference:
Patent; Shanghai Huahuituo Pharmaceutical Technology Co., Ltd.; Zhejiang Huahai Pharmaceutical Co., Ltd.; Xu Xin; Zhang Tian; Li Yunfei; Wang Guan; Zhu Weibo; Li Dongsheng; Qin Chenggang; Liu Chuanduo; Liu Lei; Wu Qimei; Yang Xuqin; Jia Jie; Wang Ying; Chen Yuhao; Wang Yijin; Ge Jian; (143 pag.)CN109897011; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 149910-98-5, name is 7-Bromoisochroman, 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 149910-98-5, Formula: C9H9BrO

Into a 500-mL round-bottom flask, was placed 7-bromoisochroman (8.48 g, 40.0 mmol, 1.0 equiv) in dioxane (200 mL)/water (20 mL). Pd(dppf)Cl2 (5.8 g, 8.0 mmol, 0.2 equiv) and CS2CO3 (26.1 g, 80.0 mmol, 2.0 equiv) (BPin)2 (2.5 eq) were added to the solution. The resulting solution was stirred for 16 hr at 90 degrees C, after which it was concentrated and purified with SiCk-gel column chromatography. This resulted in 4.6 g (44.2%) of 2-(isochroman-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane as a white solid.

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

Reference:
Patent; NOVARTIS INFLAMMASOME RESEARCH, INC.; GLICK, Gary; ROUSH, William; VENKATRAMAN, Shankar; SHEN, Dong-Ming; GHOSH, Shomir; SEIDEL, Hans Martin; FRANCHI, Luigi; WINKLER, David Guenther; OPIPARI, Anthony William Jr.; KATZ, Jason; (468 pag.)WO2020/10140; (2020); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 656-64-4, name is 3-Bromo-4-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 3-Bromo-4-fluoroaniline

N-Hydroxy-4-[(2-methoxyethyl)amino]-1,2,5-oxadiazole-3-carboximidoyl chloride (46.0 g, 0.208 mol) was mixed with water (300 mL). The mixture was heated to 60 C. 3-Bromo-4-fluoroaniline [Oakwood products, product No.013091] (43.6 g, 0.229 mol) was added and stirred for 10 min. A warm sodium bicarbonate (26.3 g, 0.313 mol) solution (300 mL water) was added over 15 min. The reaction was stirred at 60 C. for 20 min. LCMS indicated reaction completion. The reaction solution was cooled to room temperature and extracted with ethyl acetate (2*300 mL). The combined ethyl acetate solution was dried over sodium sulfate and concentrated to give the desired product (76.7 g, 98%) as a crude brown solid. LCMS for C12H14BrFN5O3 (M+H)+: m/z=374.0, 376.0. 1H NMR (400 MHz, DMSO-d6): delta 11.55 (s, 1H), 8.85 (s, 1H), 7.16 (t, J=8.8 Hz, 1H), 7.08 (dd, J=6.1, 2.7 Hz, 1H), 6.75 (m, 1H), 6.14 (t, J=5.8 Hz, 1H), 3.48 (t, J=5.2 Hz, 2H), 3.35 (dd, J=10.8, 5.6 Hz, 2H), 3.22 (s, 3H).

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 656-64-4.

Reference:
Patent; Incyte Corporation; Incyte Holdings Corporation; Combs, Andrew P.; Yue, Eddy W.; Sparks, Richard B.; Zhu, Wenyu; (63 pag.)US9320732; (2016); B2;,
Bromide – Wikipedia,
bromide – Wiktionary