Tag: M.W=200-300

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. 24358-62-1, name is 1-(4-Bromophenyl)ethylamine, A new synthetic method of this compound is introduced below., name: 1-(4-Bromophenyl)ethylamine

1-(4-bromophenyl)ethanamine 3-a (5g, 25mmol) in DCM (100ml) was added TEA (5.07g, 50mmol) and the mixture was cooled to 0C. Boc20 (8.13g, 37mmol) was added at this temperature. Then the resulting mixture was stirred at room temperature overnight. The mixture was concentrated under vacuum and the residue was washed with hexane to provide 3-b (6.17g, 82%). (M+H)+=300, 302.

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; MERCK SHARP & DOHME CORP.; ZHOU, Changyou; ZOU, Wuxin; HUA, Yuxia; DANG, Qun; WO2013/40790; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 112734-22-2, name is (4-Bromo-2-fluorophenyl)methanamine, 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. Recommanded Product: (4-Bromo-2-fluorophenyl)methanamine

To a solution of (E)-3-(4-(trifluoromethyl)phenyl)acrylic acid (67) (500 mg, 2.31 mmol) (4-bromo-2-fluorophenyl)methanamine (66) (519 mg, 2.54 mmol) in DMF (5 ml) was added HATU (924 mg, 2.43 mmol) and DIEA (0.81 ml, 4.63 mmol) at 0 C. under nitrogen. After being stirred overnight at room temperature, the reaction mixture was quenched with 10% citric acid and diluted with ethyl acetate. The resulting organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated in vacuo. The crude product was chromatographed on silica gel eluting with a gradient of hexane/ethyl acetate (20-40%) to afford 460 mg of the desired product (68) in 91% yield as a white solid. 1H-NMR (DMSO-d6) delta: 8.74 (1H, t, J=5.05 Hz), 7.79 (4H, s), 7.56-7.52 (2H, m), 7.42 (1H, d, J=8.34 Hz), 7.33 (1H, d, J=8.34 Hz), 6.81 (1H, d, J=15.66 Hz), 4.41 (2H, d, J=5.05 Hz). LC/MS (M+1): 404.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 112734-22-2, its application will become more common.

Reference:
Patent; SHIONOGI & CO., LTD.; Kurose, Noriyuki; Iso, Yasuyoshi; Yamaguchi, Naoko; Shao, Bin; Tafesse, Laykea; Zhou, Xiaoming; Yu, Jianming; US9156830; (2015); B2;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 454-79-5, 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. 454-79-5 name is 2-Bromo-5-(trifluoromethyl)aniline, 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.

Add 2-bromo-5-trifluoromethyl-aniline (10 mmol) to a reaction vessel containing 25 ml of glacial acetic acid.3-methylfuryl-2,5-dione (11 mmol) was added,The mixture was refluxed overnight and then cooled to <50 C.The solvent was transferred in vacuo, the residue was dissolved in dichloromethane (50 ml), and the resulting solution was washed with water (50 ml x 2), saturated aqueous NaHCO3 (50 ml x 2) and saturated brine (50 ml x 2), and anhydrous Dry over sodium sulfate. Evaporate the solvent in vacuumThe residue was dissolved in 15 ml of acetone, and then crystallized by dropwise addition of 30 ml of ethanol, filtered, and vacuum dried at 50C to obtain 2.9 g of white 1-(2-bromo-5-trifluoromethyl-phenyl)-3-methyl- 1H-pyrrole-2,5-dione solid, yield 87%. At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-5-(trifluoromethyl)aniline, and friends who are interested can also refer to it. Reference:
Patent; Tian Yuanqiang; (10 pag.)CN107954992; (2018); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 69321-60-4, 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. 69321-60-4, name is 2,6-Dibromotoluene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

2.362 g 2,6-dibromo-toluene (9.45 mmol) was dissolved in 10 mL dry THF under N2 atmosphere and the mixture was cooled to -78 C. Then 5.2 mL nBuLi (2.OM in pentane,10.4 mmol) was added dropwise and the mixture was stirred for 15 minutes. Then 2.31 mL2-isopropoxy-4,4,5 ,5-tetramethyl- 1,3 ,2-dioxaborolane (11.3 mmo 1) was added dropwise and the mixture was allowed to warm up to r.t.. It was stirred until no further conversion was observed. Then the mixture was quenched with aqueous NH4C1 solution, then extracted with EtOAc. The combined organic layer was dried over Na2SO4, filtered and thefiltrate was concentrated under reduced pressure. The crude product was purified via flash chromatography using heptane and EtOAc as eluents to obtain Preparation B7. 1H NMR(400 MHz, CDC13) oe: 7.67 (d, 1H), 7.62 (d, 1H), 7.10 (t, 1H), 2.53 (s, 3H), 1.29 (s, 12H)

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

Reference:
Patent; LES LABORATOIRES SERVIER; VERNALIS (R&D) LIMITED; SZLAVIK, Zoltan; SZABO, Zoltan; CSEKEI, Marton; PACZAL, Attila; KOTSCHY, Andras; BRUNO, Alain; GENESTE, Olivier; CHEN, I-Jen; DAVIDSON, James Edward Paul; MURRAY, James Brooke; ONDI, Levente; RADICS, Gabor; SIPOS, Szabolcs; PROSZENYAK, Agnes; PERRON-SIERRA, Francoise; BALINT, Balazs; (188 pag.)WO2016/207226; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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 112342-72-0 as follows. Product Details of 112342-72-0

Reference Example 444 6-bromo-2-(2,5-dimethyl-1H-pyrrol-1-yl)[1,3]thiazolo[4,5-b]pyrazine A mixture of 2-amino-6-bromo[1,3]thiazolo[4,5-b]pyrazine (8.00 g) synthesized by the method described in , n-hexane-2,5-dione (8.10 mL) and p-toluenesulfonic acid monohydrate (658 mg) in toluene (86.0 mL) was heated under reflux overnight. Under ice-cooling, saturated aqueous sodium hydrogen carbonate solution was added and the mixture was extracted twice with chloroform. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated, and the obtained residue was purified by silica gel column chromatography (solvent; hexane/ethyl acetate=100/0 – 80/20) to give the title compound (8.33 g). MS(ESI)m/z; 309,311[M+H]+

According to the analysis of related databases, 112342-72-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Mitsubishi Tanabe Pharma Corporation; OKUYAMA, Masahiro; FUKUNAGA, Kenji; USUI, Kenji; HAYASHI, Norimitsu; IIJIMA, Daisuke; HORIUCHI, Hideki; FUJIMOTO, Nobuaki; (218 pag.)EP3372601; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 141474-37-5, name is 2,4-Dibromo-6-fluoroaniline, 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 141474-37-5, Recommanded Product: 2,4-Dibromo-6-fluoroaniline

compound 2,4-dibromo-6-fluroaniline (2,4-dibromo-6-fluoroaniline) 40 g (149 mmol),phenylboronic Acid (Phenylboronic acid) 39.9 g (327 mmol),Tetrakis (triphenylphosphine) palladium (0), 8.59 g (7.44 mmol),K2CO3 82 g (595 mmol), Toluene (Toluene) 600 mL, H2O 150 mL Put the nitrogen was replaced. 24 hours of reaction at 100 degree and Distilled water and dichloromethane (MC), and extracted using NaCl. With a rotary evaporator after the organic layer was dried over anhydrous MgSO4After removal of the solvent hexane (Hexane): dichloromethane (MC) = 20: 1 using a column chromatography (columnPurification by chromatography) to obtain 32.9 g of the desired compound 2-3 (85%).

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, 2,4-Dibromo-6-fluoroaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hee Sung Material Co., Ltd; Kim, Ji Hee; Jang, So Hyun; Kim, Yeong Woo; Kim, Hyun Dong; Uhm, Song Jin; Lee, Ju Dong; (50 pag.)KR2016/1508; (2016); A;,
Bromide – Wikipedia,
bromide – Wiktionary

4549-33-1, name is 1,9-Dibromononane, 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. Application In Synthesis of 1,9-Dibromononane

General procedure: A solution of 2 0.5 g (2 mmol) and anhydrous CH3CN (10 ml) was treated with dihalogenid (1 mmol) and heated on a bath at 70-75 C for different time from 10 to 30 h depending on dihalogenide structure. The solvent was removed at reduced pressure. The resulting precipitate was chromatographed over silica gel ((CHCl3+NH4OH)/MeOH eluent, (100:0?0:100)).

The synthetic route of 4549-33-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sokolova, Anastasiya S.; Yarovaya, Olga I.; Shernyukov, Andrey V.; Pokrovsky, Michail A.; Pokrovsky, Andrey G.; Lavrinenko, Valentina A.; Zarubaev, Vladimir V.; Tretiak, Tatiana S.; Anfimov, Pavel M.; Kiselev, Oleg I.; Beklemishev, Anatoly B.; Salakhutdinov, Nariman F.; Bioorganic and Medicinal Chemistry; vol. 21; 21; (2013); p. 6690 – 6698;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 454-79-5, name is 2-Bromo-5-(trifluoromethyl)aniline, 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 454-79-5, name: 2-Bromo-5-(trifluoromethyl)aniline

2-Bromo-5-(trifluoromethyl)aniline (2.0 g, 8.3 mmol),4-(pinacol ester-2-yl)-5,6-dihydropyridine-1(2H)-carboxylic acid tert-butyl ester (3.1 g, 10 mmol),Potassium acetate (1.23 g, 12.5 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]palladium dichloride (343 mg, 0.42 mmol) were added to N,N-dimethylformamide ( Mix of 30mL) and water (2mL)In the solvent, the reaction was heated to 90 C for 16 hours under a nitrogen atmosphere. The reaction was quenched and cooled to room temperature. The mixture was poured into water (100 mL), dichloromethane (30 mL¡Á3) (Dichloromethane: methanol (V: V) = 50: 1) isolated and purified to give the title compound(Yellow solid, 2.42 g, 85%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-5-(trifluoromethyl)aniline, and friends who are interested can also refer to it.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jin Chuanfei; Zhang Yingjun; Xue Yaping; Guo Zhengjiang; (39 pag.)CN109912514; (2019); A;,
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. 502496-36-8, name is 3-Bromo-5-fluoro-2-methylaniline, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C7H7BrFN

To a solution of 3-bromo-5-fluoro-2-methyl-phenylamine (470mg) in dioxane (6 mL) was added triethylamine (1.28 mL), palladium acetate (25 mg), 2-dicyclohexylphosphino biphenyl (161mg) and pinacol borane (1.001ml) and the mixture was heated to 8O0C for 4 h. The reaction mixture was cooled, diluted with chloroform, washed with brine, dried (MgSO4) and the solvent removed in vacuo. The residue was purified using flash chromatography to yield 45 (466 mg).

According to the analysis of related databases, 502496-36-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GENENTECH, INC.; F. HOFFMANN – LA ROCHE AG; WO2009/42607; (2009); 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. 3875-78-3, name is 6-Bromochroman, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 3875-78-3

To a mixture of 6-bromochromane (2.0 g, 9.43 mmol, 1.00 equiv) in THF (20 ml_) was added n-BuLi (2.5 M in hexane, 3.76 ml_, 1.00 equiv) dropwise at – 78C. The reaction mixture was stirred at -78C for 30 min. To the mixture was then added a solution of 4-(benzyloxy)-5-bromo-2-methoxybenzaldehyde (2.74 g, 8.56 mmol, 0.91 equiv) in THF (2 ml_) dropwise at -78C. The reaction mixture was stirred for 2 h at -78C. NH4CI/H2O was added and the mixture was extracted with EtOAc thrice. The combined extracts were washed with brine and dried over Na2SC>4. The mixture was concentrated and the resulting residue purified by chromatography on silica gel (3: 1 PE/EA) to yield (4-(benzyloxy)-5-bromo-2-methoxyphenyl)(chroman-6-yl)methanol as a colorless oil.

According to the analysis of related databases, 3875-78-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; GUOZHANG, Xu; KUO, Gee-Hong; GAUL, Micheal; (163 pag.)WO2019/215633; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary