Month: July 2021

Electric Literature of 30273-40-6, 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. 30273-40-6, name is 4-Bromo-2,5-dimethylaniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Into a 25-mL 3-necked round-bottom flask under N2 atmosphere, was placed 4-allyl- 1 – methyl- 1 H-pyrazole-5 -carboxylic acid (0.843 g, 5.07 mmol, 1 equiv), 4-bromo-2,5- dimethylaniline (1.0 g, 5.00 mmol, 0.99 equiv), HATU (2.9 g, 7.63 mmol, 1.50 equiv), DIEA (1.3 g, 10.15 mmol, 2 equiv) and DMF (10 mL). The resulting solution was stirred overnight at room temperature. The reaction was then quenched with water and the resulting solution was extracted with ethyl acetate. The combined organic layer was concentrated under reduced pressure. The residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1 : 10) to give 1.2 g (67.93%) oftitle compound as a white solid. LC-MS: (ES, m/z): [M+H]+ 348.

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

Reference:
Patent; IDEAYA BIOSCIENCES, INC.; ALAM, Muzaffar; ASWAD, Fred; BECK, Hilary Plake; DILLON, Michael Patrick; GONZALEZ-LOPEZ, Marcos; HATA, Yujiro; SUTTON, JR., James Clifford; (0 pag.)WO2019/236766; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 1753-75-9,Some common heterocyclic compound, 1753-75-9, name is 5-Bromobenzo[c][1,2,5]thiadiazole, molecular formula is C6H3BrN2S, 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.

Benzo[1 ,2,5]thiadiazol-5-yl-(8-chloro-[1 ,2,4]triazolo[1 ,5-a]pyrazin-2-yl)-amine (“BIO”)100 mg (0.6 mmol) of 8-pyridin-3-yl-[1 ,2,4]triazolo[1 ,5-a]pyrazin-2-ylamine, mg (0.9 mmol) 5-bromo-2,1 ,3-benzothiadiazole, 68 mg (0.1 mmol) 9,9- dimethyl-4,5-bis(diphenylphosphino)xanthene , 578 mg (1.8 mmol) cesium carbonate and 34 mg bis(dibenzylideneacetone)palladium are dissolved in 1 ml dioxane and stirred at 90 C for 14 h. HPLC and LC-MS analysis show formation of the product (LCMS (method C): mass found (M+H+, 303), HPLC (method D) Rt (min): 3.07.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromobenzo[c][1,2,5]thiadiazole, its application will become more common.

Reference:
Patent; MERCK PATENT GMBH; BURGDORF, Lars; SCHULTZ, Melanie; DEUTSCH, Carl; COMAS, Horacido; SWINNEN, Dominique; POMEL, Vincent; GAILLARD, Pascale; HODOUS, Brian; WO2012/25186; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 114078-88-5, name is 5-Bromo-1,2,3-triazine, 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 114078-88-5, Computed Properties of C3H2BrN3

To a solution of compound S3 (400 mg, 2.5 mmol) in CHCl3(10 mL) was added 1-(cyclopent-1-en-1-yl)pyrrolidine (516 mg, 3.8 mmol). The reaction was stirred at 45 C. for 16 hrs. The reaction mixture was diluted with DCM and washed water, brine, dried over anhydrous Na2SO4, filtered, and concentrated. The residue was purified by silica gel column (eluted with EtOAc/PE=1/10) to give the title compound (170 mg, 34.3% yield) as a gray solid.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; PHADKE, Avinash, S.; DESHPANDE, Milind; AGARWAK, Atul; CHEN, Dawei; GADHACHANDA, Venkat, Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; (905 pag.)WO2017/35353; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 4333-56-6, These common heterocyclic compound, 4333-56-6, name is Bromocyclopropane, 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.

To a stirred suspension of potassium fert-butoxide (8.00 g, 71.33 mmol) in DMSO (70 mL) under nitrogen was added 3-mercaptophenol (5 g, 39.63 mmol) at 0 C; the reaction was stirred at room temperature for 30 min. Then bromocyclopropane (5.72 mL, 71.33 mmol) was added into the reaction mixture. The reaction was heated at 90C overnight. After the reaction was completed, it was diluted with EtOAc. The organic layer was washed with water, saturated NH4CI aqueous solution (2x), and brine. The aqueous layer was back extracted with EtOAc (lx). The combined organic layers were dried over Na2S04, filtered and concentrated. The residue was purified by silica gel column chromatography to give the title compound (6.19 g, 85% yield). LCMS m/z = 167.2 [M+H]+; NMR (400 MHz, CDCI3) delta ppm 0.68-0.74 (m, 2H), 1.05-1.12 (m, 2H), 2.13-2.22 (m, 1H), 4.75 (s, 1H), 6.60 (dt, / = 8.08, 1.26 Hz, 1H), 6.89 (t, 7 = 2.27 Hz, 1H), 6.93 (ddd, 7 = 7.83, 1.64, 0.88 Hz, 1H), 7.15 (t, 7 = 7.96 Hz, 1H

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

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; TRAN, Thuy-Anh; DO, Quyen-Quyen; ULLMAN, Brett; (259 pag.)WO2017/214002; (2017); 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. 2051-99-2, name is 1-Bromo-4-isobutylbenzene, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 2051-99-2

Intermediate A6 2-(4-isobutylphenyl)-6-methoxy-3.4-dihvdroisoquinolin-l(2H)-one vial, 6-methoxy-3,4-dihydroisoquinolin-l(2H)-one (0.25 g, 1.411 mmol) was dissolved in N-dimethylformamide (2.82 ml). To this was added l-bromo-4-isobutylbenzene (0.451 g, 2.116 mmol) and potassium carbonate (0.390 g, 2.82 mmol). The reaction mixture was flushed with nitrogen, charged with copper(I) iodide (0.161 g, 0.847 mmol) and heated to 150 C for 24 h. The reaction mixture was cooled to room temperature, quenched with water and extracted three times with dichloromethane. The organic layers were combined, passed through a phase separator and concentrated. The crude material was purified via silica gel chromatography using 0-75% ethyl acetate in heptanes to afford the desired product (190 mg, 0.614 mmol, 43.5 % yield) as a light orange solid. NMR (400 MHz, Chloroform-d) delta 8.12 (d, J = 8.7 Hz, 1H), 7.32 – 7.27 (m, 2H), 7.24 – 7.15 (m, 2H), 6.89 (dd, J = 8.7, 2.6 Hz, 1H), 6.77 – 6.65 (m, 1H), 3.96 (dd, J = 7.0, 6.0 Hz, 2H), 3.86 (s, 3H), 3.09 (t, J = 6.4 Hz, 2H), 2.50 (d, J = 7.1 Hz, 2H), 1.90 (dh, J = 13.5, 6.8 Hz, 1H), 0.94 (d, J = 6.6 Hz, 6H). LC MS (m/z, MH+): 310.4.

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 2051-99-2.

Reference:
Patent; NOVARTIS AG; BURKS, Heather Elizabeth; KARKI, Rajeshri Ganesh; KIRBY, Christina Ann; NUNEZ, Jill; PEUKERT, Stefan; SPRINGER, Clayton; SUN, Yingchuan; THOMSEN, Noel Marie-france; WO2015/92634; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 129316-09-2,Some common heterocyclic compound, 129316-09-2, name is 1,3-Dibromo-5-(tert-butyl)benzene, molecular formula is C10H12Br2, 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.

Step 1: tert-Butyl 3-bromo-5-(tert-butyl)benzoate (11a) n-Butyl lithium (7.2 mL, 18.0 mmol, 2.5M in THF) was added to a 100 mL flask under nitrogen atmosphere containing 9 mL of toluene at -10C. n-Butylmagnesium chloride (4.5 mL, 9.0 mmol, 2M in THF) was then added at such a rate to keep the temperature below -5C. The resulting milky slurry was aged at -10C for 30 min. To this slurry was added 1,3-dibromo-5-(tert-butyl)benzene (6.2 g, 21.2 mmol) dissolved in 20 mL of toluene. The rate of addition was such that the temperature did not increase above -5C. After addition was complete, the mixture was kept at -10C until the metal-halogen reaction was complete. A solution of di-tert-butyl dicarbonate (5.89 g, 27 mmol) in 7.5 mL of toluene was then charged such at a rate to keep the temperature below -5C. After the addition was complete, the mixture was kept at -10C until the aryl-Mg intermediate was completely consumed. The mixture was quenched by the addition of 40 mL of a 10% (w/w) aqueous solution of citric acid, which resulted in an exothermic generation of carbon dioxide. The phases were separated and the organic layer was washed with another 40 mL of citric acid solution. The organic extracts were then dried with MgSO4 and the solvents were removed at reduced pressure. Compound 11c was obtained as a brown oil (4.0 g, 60%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,3-Dibromo-5-(tert-butyl)benzene, its application will become more common.

Reference:
Patent; Phenex Pharmaceuticals AG; EP2511263; (2012); 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. 630-17-1, name is 1-Bromo-2,2-dimethylpropane, A new synthetic method of this compound is introduced below., Quality Control of 1-Bromo-2,2-dimethylpropane

Lambda/-(1 -Methylcyclopropyl)-3-((3-methylisoxazol-5-yl)methyl)-2,4-dioxo-1 ,2,3,4- tetrahydroquinazoline-6-sulfonamide (100 mg, 0.260 mmol), cesium carbonate (100 mg, 0.3100 mmol), sodium iodide (8 mg, 0.05 mmol) and 1 -bromo-2,2-dimethylpropane (426 mg, 2.8 mmol) in DMF (2 mL) was heated by microwave irradiation to 130 C for 1 .5 h. The reaction mixture was diluted with water (10 mL) and extracted with EtOAc (2 x 20 mL). The organic phase was combined, washed with brine (10 mL), passed through a hydrophobic frit and evaporated to dryness. The crude product mixture was purified by prep HPLC (high pH) to give the desired product (14 mg, 0.03 mmol, 12%) as an off-white powder

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; CANCER RESEARCH TECHNOLOGY LIMITED; MCGONAGLE, Alison E.; JORDAN, Allan; WASZKOWYCZ, Bohdan; HUTTON, Colin; WADDELL, Ian; HITCHIN, James R.; SMITH, Kate Mary; HAMILTON, Niall M.; (497 pag.)WO2016/92326; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 69272-50-0, These common heterocyclic compound, 69272-50-0, name is 3,6-Dibromobenzene-1,2-diamine, 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.

3,6-Dibromobenzene-1,2-diamine with round flask equipped with a condenser (compound 2-a) (1g) and phenanthrene-9,10-dione (0.8 g) after the into the respective acetate, 30mL ethanol and 30 after the injection, each mL, was added the temperature to 80 C, and reacted for 24 hours. If after the completion of the reaction through the methanol, the resulting solid filter using methanol to afford a yellow solid 10,13-dibromodibenzo [a, c] phenazine (compound C). (Yield: 68%).

Statistics shows that 3,6-Dibromobenzene-1,2-diamine is playing an increasingly important role. we look forward to future research findings about 69272-50-0.

Reference:
Patent; Pusan National University Industry-Academic Cooperation Foundation; Hwang, Do Hun; Kim, Ji Hun; Kim, Hee Woon; Im, Jong Min; (52 pag.)KR101495152; (2015); B1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 6627-78-7,Some common heterocyclic compound, 6627-78-7, name is 1-Bromo-4-methylnaphthalene, molecular formula is C11H9Br, 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.

General procedure: To a flame dried, 3 times evacuated and argon purged 25mL Schlenk flask was added 4.6mmol of aryl bromide (2-bromo-9,9-dimethylfluorene, 9-bromoanthracene, and 1-bromo-4-methylnaphthalene) and a magnetic stir bar. The flask was then cooled to -78 C (dry ice/acetone bath) for 10min under argon (room temperature for phenylacetylide). Then 10mL of dry argon purged diethyl ether was added to the reaction and allowed to cool for another 10min. This was followed by 2.2mL (5.5 mmol) of n-butyllithium solution in diethyl ether. The reaction was allowed to stir for 30min to complete the halide-exchange reaction, at which time the reactions turned a yellow color and salt precipitates formed. Then 1 g (3.8mmol) of spirosiloxane I dissolved in 5mL of cooled dry argon purged diethyl ether was added by syringe to the reaction mixture and allowed to stir for an additional 2 h. The reaction was run till the yellow color subsided and was then quenched with excess Me3SiCl and allowed to stir cold for >30min before warming up. The reaction was then worked up by a quick water wash (2 times) to remove salts and then dried over MgSO4. The reaction was then filtered through Celite to remove salts and solvent removed in vacuo. Yellow-orange viscous oils were obtained. Characterization is given in tabular form in the text.

The synthetic route of 6627-78-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Furgal, Joseph C.; Laine, Richard M.; Bulletin of the Chemical Society of Japan; vol. 89; 6; (2016); p. 705 – 725;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 4549-33-1,Some common heterocyclic compound, 4549-33-1, name is 1,9-Dibromononane, molecular formula is C9H18Br2, 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.

1,9-Dibromononane (610 muL, 3 mmol) was added to a stirred solution of the product of Preparation 1 (377 mg, 1 mmol) and DIPEA (1.05 mL, 6 mmol) in DMF (5 mL) at 50 C. The reaction mixture was heated at 80 C. for 72 h and then the solvent was removed under reduced pressure. The crude residue was purified by flash chromatography (10% MeOH in DCM containing 0.5% NH4OH) to give the title compound (292 mg, 0.5 mmol, 50%).

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

Reference:
Patent; Mammen, Mathai; Hughes, Adam; US2004/242622; (2004); A1;,
Bromide – Wikipedia,
bromide – Wiktionary