Month: June 2021

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, Recommanded Product: 7-Bromoisochroman

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

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. 4333-56-6, name is Bromocyclopropane, A new synthetic method of this compound is introduced below., HPLC of Formula: C3H5Br

[000459j A mixture of Compound 19A (2.0 g, 10 mmol), bromocyclopropane (2.4 g, 20 mmol), Cs2CO3 (9.8 g, 30 mmol) in DMSO (40 mL) was stirred at 170 C for 2 days under high pressure. The mixture was cooled to room temperature and filtered through celite. The filtrate was diluted with ethyl acetate (100 mL), washed with brine (100 mL x 2), dried over sodium sulfate, and concentrated. The crude was purified with column chromatography on silica gel (petroleum ether, 100% v/v) to render Compound 19B. LC-MS (mlz): 247 [M+1] ?H-NMR (CDC13, 400 MHz) major characteristic peaks: 5 (ppm) 0.78-0.82 (m, 4H), 3.7 1-3.73 (m, 1H), 6.95-6.95 (m, 1H), 7.13-7.18 (m, 1H), 7.34-7.36 (m, 1H).

The synthetic route of 4333-56-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOMARIN PHARMACEUTICAL INC.; WANG, Bing; WO2015/65937; (2015); 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., name: 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

Related Products 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

Synthetic Route 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

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

Some common heterocyclic compound, 185122-74-1, name is 5-Bromo-2,3-dihydro-1H-inden-1-amine, molecular formula is C9H10BrN, 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. name: 5-Bromo-2,3-dihydro-1H-inden-1-amine

To a suspension of 5-bromo-2,3 -dihydro- lH-inden-1 -amine (2.2 g, 10.4 mmol) and NaHC03 (2.6 g, 31.2 mmol) in MeCN (100 mL) was added Boc20 (3.4 mL, 15.6 mmol) at 0 C. The reaction was stirred at rt overnight, then concentrated in vacuo. The residue was dissolved in EtOAc (100 mL). The resulted solution was washed with H20 (50 mL x 2), dried over anhydrous a2S04, filtered and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (v/v) =20/1) to give the title compound as a white solid (3.3 g, 100%). MS (ESI, pos. ion) m/z: 257 [M + H – 56]+; NMR (400 MHz, i/6-DMSO) delta (ppm): 1.48 (s, 9H), 1.72-1.85 (m, 1H), 2.49-2.62 (m, 1H), 2.77-2.88 (m, 1H), 2.89-2.98 (m, 1H), 4.67-4.77 (br, 1H), 5.07-5.17 (m, 1H), 7.18 (d, J= 8.0 Hz, 1H), 7.32 (d, J= 8.0 Hz, 1H), 7.36 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 185122-74-1, its application will become more common.

Reference:
Patent; CALITOR SCIENCES, LLC; SUNSHINE LAKE PHARMA CO., LTD; XI, Ning; WANG, Ruyong; WANG, Liang; WO2014/89324; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 5279-32-3, name is 5,6-Dibromobenzo[d][1,3]dioxole, molecular formula is C7H4Br2O2, 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 5,6-Dibromobenzo[d][1,3]dioxole

Under nitrogen atmosphere, 5,6-Dibromo-1,3-benzodioxole (13a, 1.58 g, 5.64 mmol), zinc(II)cyanide (670 mg, 5.71 mmol) and [1,1?-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (208 mg, 284 mumol) were dissolved in anhydrous dimethylacetamide (12 mL) andstirred for 3 h at 150 C. Subsequently, the mixture was diluted with ethyl acetate (50 mL),washed with water (2 × 50 mL), the organic layer dried over magnesium sulfate and the solventremoved in vacuo. The crude product was purified by column chromatography using silica anddichloromethane as eluent (Rf = 0.50) to obtain a colourless solid (829 mg, 4.82 mmol, 85%).1H NMR (500MHz, CDCl3, 300 K): delta = 7.14 (s, 2H), 6.21 (s, 2H) ppm;13C NMR (125 MHz, CDCl3, 300 K): delta = 151.7 (2C), 115.5 (2C), 112.8 (2C), 111.0 (2C), 104.0 ppm;MS (EI, 70 eV): m/z (%) = 172 (100) [M]+;HR-MS (EI, 70 eV): m/z = calcd. for C9H4N2O2 [M]+ 172.0267, found 172.0273.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5279-32-3, its application will become more common.

Reference:
Article; Hamer, Sebastian; Roehricht, Fynn; Jakoby, Marius; Howard, Ian A.; Zhang, Xianghui; Naether, Christian; Herges, Rainer; Beilstein Journal of Organic Chemistry; vol. 15; (2019); p. 1331 – 1338;,
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. 112734-22-2, name is (4-Bromo-2-fluorophenyl)methanamine, A new synthetic method of this compound is introduced below., HPLC of Formula: C7H7BrFN

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 1N HCl 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%).

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; Gruenenthal GmbH; FRANK, Robert; Bahrenberg, Gregor; Christoph, Thomas; Lesch, Bernhard; Lee, Jeewoo; US2013/79320; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 586-61-8, The chemical industry reduces the impact on the environment during synthesis 586-61-8, name is 1-Bromo-4-isopropylbenzene, I believe this compound will play a more active role in future production and life.

[0001248] A mixture of l-bromo-4-isopropylbenzene (30 mg, 0.15 mmol), Compound 356A (75 mg, 0.15 mmol), [l, -bis(diphenylphosphino)ferrocene]dichloropalladium(II) (7 mg, 8.2 muiotaetaomicron), sodium carbonate (32 mg, 0.30 mmol), water (0.5 mL), and 1,4-dioxane (5 mL) was stirred under nitrogen atmosphere at 80 C for 2 h. After cooling, the reaction mixture was treated with water (5 mL), extracted with ethyl acetate (10 mL x 3), washed with brine (5 mL), dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified with prep-HPLC to furnish Compound 357. LC-MS (ESI) m/z: 547 [M+H]+; 1H- NMR ((CD3)2CO, 400 MHz): delta (ppm) 1.64 (m, 6H), 2.08-2.11 (m, 3H), 2.17-2.23 (m, 1H), 2.96-3.043 (m, 4H), 3.17-3.82 (m, 4H), 4.21-4.33 (m, 3H), 4.37 (d, 1H), 4.69-5.75 (m, 2H), 6.85-7.07 (m, 2H), 7.35-7.43 (m, 2H), 7.46-7.79 (m, 3H), 7.81-7.87 (m, 1H), 7.89-7.98 (m, 1H), 8.02-8.14 (m, 1H).

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, 1-Bromo-4-isopropylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BIOMARIN PHARMACEUTICAL INC.; WANG, Bing; CHU, Daniel; BRIDGES, Alexander, James; WO2015/42397; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary