Month: August 2021

Reference of 43204-63-3, A common heterocyclic compound, 43204-63-3, name is Bis(2-Bromoethyl)amine hydrobromide, molecular formula is C4H10Br3N, 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.

Step 4: 5-Fluoro-2-(piperazin-1-yl)benzenesulfonamide A mixture of 2-amino-5-fluoro-benzenesulfonamide (950.00 mg, 4.99 mmol), 2-bromo-N-(2-bromoethyl) ethanamine hydrobromide (7.78 g, 24.95 mmol) and n-butyl alcohol (50.00 mL) was stirred at 120 C. for 24 h. The reaction mixture was allowed to cool to rt. Filtered and the filtrate was used for the next step directly. MS (EI+, m/z): 260.2 [M+H]+

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; Navitor Pharmaceuticals, Inc.; O’Neill, David John; Saiah, Eddine; Kang, Seong Woo Anthony; Brearley, Andrew; Bentley, Jonathan; (519 pag.)US2018/127370; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 202865-83-6, name is 1-Bromo-3-fluoro-5-methylbenzene, 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. SDS of cas: 202865-83-6

Example AAA00110 Synthesis of 4-(thiazol-2-yl)-1-(3-(3-fluoro-5-methylphenyl)-propiolyl)piperazine 4-(Thiazol-2-yl)-1-(3-(3-fluoro-5-methylphenyl)propiolyl)piperazine was obtained by the reaction of 4-(thiazol-2-yl)-1-propiolylpiperazine [Precursor BBB2] with 3-bromo-5-fluorotoluene under the conditions described in the case of Example AAA35.

The synthetic route of 1-Bromo-3-fluoro-5-methylbenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Gruenenthal GmbH; US2007/112011; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 937046-98-5, 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. 937046-98-5, name is 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine, This compound has unique chemical properties. The synthetic route is as follows.

To a suspension of N-methyltetrahydro-2H-pyran-4-amine (541 mg, 4.69 mmol) and (3-(bromomethyl)phenyl)boronic acid (756 mg, 3.52 mmol) in acetonitrile (8 mL) was added K2C03 (973 mg, 7.04 mmol) under anhydrous conditions. After stirring at room temperature for 10 h, the reaction mixture was concentrated, phosphoric acid,potassium salt (1.50 g, 2.35 mmol), 7-bromopyrrolo[2,1-f][1,2,4]triazin-4-amine (500 mg, 2.347 mmol), dioxane (8 mL) and water (4 mL) were added. The reaction vessel was evacuated, backfilled with N2 and then degassed by bubbling N2 with sonication. Tetrakis triphenylphosphine (271 mg, 0.235 mol) was added and the degassing process was repeated. The resulting reaction mixture was heated at 140 C in a microwave for 45mm. The reaction complex was cooled, filtered, and washed with water. The filtrate was extracted with ethyl acetate (10 mL x 3). The organic layers were combined, dried and concentrated. The crude mixture was dissolved in DMF, and purified by preparative LC Method C to obtain 7-(3 -((methyl(tetrahydro-2H-pyran-4-yl)amino)methyl)phenyl) pyrrolo[2,1-f][1,2,4]triazin-4-amine, TFA (636 mg, 60% yield). LC/MS (M+H) =338.30.

The chemical industry reduces the impact on the environment during synthesis 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BHIDE, Rajeev S.; BATT, Douglas G.; CHERNEY, Robert J.; CORNELIUS, Lyndon A.M.; LIU, Qingjie; MARCOUX, David; NEELS, James; POSS, Michael A.; QIN, Lan-ying; RUAN, Zheming; SHI, Qing; SRIVASTAVA, Anurag S.; TINO, Joseph A.; WATTERSON, Scott Hunter; (532 pag.)WO2016/64957; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 43204-63-3, 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. 43204-63-3 name is Bis(2-Bromoethyl)amine hydrobromide, 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.

Formula X A mixture of 0.1 mol of bis-bromoethylamine hydrobromide and 0.1 mol of 2,4-difluoroaniline in 50 ml of butan-1-ol is heated at the boil for 14 hours. The reaction mixture is then cooled and the precipitate obtained is filtered off. The crystals are taken up with water and the mixture is rendered basic in the cold with a 10% solution of sodium hydroxide. The aqueous phase is extracted with chloroform and the extract is washed with water, dried over sodium carbonate and filtered. The chloroform is evaporated off and the residue obtained is taken up with acetone. Hydrogen chloride gas is bubbled through this solution, with stirring, until the pH is acid, and the crystals formed are allowed to settle. The crystals obtained are filtered off and then washed with acetone and dried. 4-(2,4-Difluorophenyl)piperazine dihydrochloride is thus recovered in the form of crystals melting at 205 C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Bis(2-Bromoethyl)amine hydrobromide, and friends who are interested can also refer to it.

Reference:
Patent; Centre D’Activite Et De Recherches Pharmaceutique Industrielle Biologique Medicale; US4886805; (1989); A;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 51376-06-8, name is 5-Bromobenzo[c][1,2,5]oxadiazole, 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. SDS of cas: 51376-06-8

General procedure: Methyl 5-boronofuran-2-carboxylate (8, 1.3mmol), the appropriate bromo derivatives (10, or 12, or 13, 1.0mmol) and bis(triphenylphosphine)palladium (II) dichloride (5% mol) were dissolved in dry 1,4-dioxane (10mL), under nitrogen atmosphere. A 2M sodium carbonate solution (2mmol) was then added and the resulting mixture was stirred in a microwave synthesizer (Biotage Initiator Classic) for 1hat 60C. After completion, the solution was cooled to room temperature and then filtered on a celite pad. The filtrate was diluted with water and extracted with ethyl acetate (3×4mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo.

The synthetic route of 5-Bromobenzo[c][1,2,5]oxadiazole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chiarelli, Laurent R.; Mori, Matteo; Barlocco, Daniela; Beretta, Giangiacomo; Gelain, Arianna; Pini, Elena; Porcino, Marianna; Mori, Giorgia; Stelitano, Giovanni; Costantino, Luca; Lapillo, Margherita; Bonanni, Davide; Poli, Giulio; Tuccinardi, Tiziano; Villa, Stefania; Meneghetti, Fiorella; European Journal of Medicinal Chemistry; vol. 155; (2018); p. 754 – 763;,
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. 1073-39-8, name is 3-Bromobicyclo[4.2.0]octa-1,3,5-triene, A new synthetic method of this compound is introduced below., name: 3-Bromobicyclo[4.2.0]octa-1,3,5-triene

4-bromobenzocyclobutene[4-bromobenzocyclobutene] (4.23 mL, 34 mmol) was dissolved in tetrahydrofuran[THF] (100 mL) and then charged into a dry ice / acetone bath [dry ice/acetone bath] to lower the furnace temperature.n-BuLi (13 mL, 32 mmol, 2.5 M in hexane) was slowly added and stirred for 1 hour.Then 9-fluorenone [9-fluorenone](3.6 g, 20 mmol) was added thereto, followed by stirring overnight.The reaction was stopped with water and extracted with ethyl acetate water.After the organic layer was collected, the organic layer was dried and filtered using MgSO4.The filtrate was dried with a vacuum rotary concentrator to remove the organic solvent,The residue was column purified to give 4.32 g (76% yield) of intermediate 1-1.

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; LG Chem, Ltd.; Seo Min-seop; Lee Jae-cheol; Kim Jin-seok; Bae Jae-sun; Kim Byeong-jae; (47 pag.)KR2019/60484; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 1435-52-5, These common heterocyclic compound, 1435-52-5, name is 1,4-Dibromo-2-fluorobenzene, 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.

150ml three-necked flask, Add 0.01 mol of 2,5-dibromofluorobenzene, 0.012 mol of M2 0.02mol sodium carbonate and 10ml ethylene glycol dimethyl ether, protected by nitrogen Heat to 190 ° C and stir the reaction for 48 hours. Then cooled to room temperature and poured into a beaker. Add 50 ml of toluene and 50 ml of water and stir for 20 minutes. Filtered, the filtrate is steamed, Pass the silica gel column, Obtaining white intermediate 3a with a purity of 98.10percent, The yield was 77.5percent.

The synthetic route of 1435-52-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangsu March Optoelectric Technology Co., Ltd.; Ye Zhonghua; Zhang Zhaochao; Li Chong; Zhang Xiaoqing; (57 pag.)CN109575057; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 1073-39-8, name is 3-Bromobicyclo[4.2.0]octa-1,3,5-triene, molecular formula is C8H7Br, 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. COA of Formula: C8H7Br

The synthesis of a tetracene brominated in the 2-position is shown by way of example in the following illustration: In a first step, alpha-chloro-o-xylene 1 was subjected to pyrolysis at approximately 800 C. and 0.5 mbar. Benzocyclobutene 2 was obtained in a 45% yield. The selective bromination thereof was carried out by treating benzocyclobutene, dissolved in acetic acid, with a mixture of bromine and iodine at room temperature, resulting in 4-bromobenzocyclobutene 3. Dissolving in toluene and heating with a slight molar excess of 1,4-dihydro-1,4-epoxynaphthalene 4 at 220 C. for 20 hours resulted in an 80% yield of a pure endo/exo mixture of the Diels-Alder addition product 5, a colorless crystalline material. This material was heated at reflux in acetic anhydride in the presence of concentrated hydrochloric acid, thus forming 9-bromo-6,11-dihydrotetracene 6. The Yamamoto coupling then resulted in 2-(5,12-dihydrotetracene-2-yl)-5,12-dihydrotetracene 7. The coupling reaction was carried out in an approximately 80% yield in a mixture of dimethylformamide and toluene at 80 C., using bis(cyclooctadienyl) nickel(0) in stoichiometric quantities. After recrystallization from o-dichlorobenzene, compound 7 was dehydrogenated by treatment with 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) in boiling o-xylene. After purification by repeated vacuum sublimation, orange-red crystals of 2-(tetracene-2-yl) tetracene 8 were obtained in a yield of 75%. All intermediate products were characterized by 1H and 13C NMR spectroscopy and mass spectroscopy. Compound 8 was characterized by UV-visible spectroscopy.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1073-39-8, its application will become more common.

Reference:
Patent; Rehahn, Matthias; Roth, Michael; Von Seggern, Heinz; Schmechel, Roland; Ahles, Marcus; US2008/214838; (2008); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 111721-75-6, A common heterocyclic compound, 111721-75-6, name is 2-Bromo-3-fluoroaniline, molecular formula is C6H5BrFN, 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.

In a 50 mL microwave tube, to a solution of 20 mL of 1 ,4-dioxane and 3 mL of water degassed with argon for 15 minutes, were successively added, 900 mg (4.73 mmol) of 2-bromo-3-fluoroaniline, 2.64 g (11.84 mmol) of 3-fluoro-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyridine, 1798 mg (11.84 mmol) of cesium fluoride, 216 mg (0.237 mmol) of tris(dibenzylideneacetone)pailadium(0) and 194 mg (0.474 mmol) of S-Phos. The reaction mixture was heated under microwave at 150 C for 1 hour. The cooled reaction mixture was diluted with ethyl acetate and filtered over a pad of Celite. The organic phase was washed by brine and dried over magnesium sulfate. The organic phase was concentrated under vacuo and purified by column chromatography on silica gel (40 g cartridge – gradient n-heptane/ethyl acetate) to yield 775 mg (72%) of 2-(3-fluoropyridin-4-yl)aniline. LogP = 2.38. Mass (M+H) = 207.

The synthetic route of 111721-75-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER AKTIENGESELLSCHAFT; CRISTAU, Pierre; DESBORDES, Philippe; DUFOUR, Jeremy; GOURGUES, Mathieu; LAMPRECHT, Sybille; LOQUE, Dominique; MEISSNER, Ruth; NAUD, Sebastien; THOMAS, Vincent; (90 pag.)WO2020/79173; (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. 454-79-5, name is 2-Bromo-5-(trifluoromethyl)aniline, A new synthetic method of this compound is introduced below., SDS of cas: 454-79-5

Step 7: Preparation of 2-Pyridin-2-yl-5-trifluoromethyl-phenylamine (24). A screw cap tube was charged with 2-tributyltinpyridine (1.4 eq), prepared from 2-bromopyridine and tributyltin hydride according to the procedure described in example 19-1, o-bromoaniline (200 mg, 1 eq), Pd(dba)2 (10-14 mg, 2 mol%), CuI (20-mg, 10 mol%), and PPh3 (40 mg, 15 mol%). The mixture was degassed and back-filled with argon. Dry diethyl ether (5 ml) was added, and the reaction mixture was heated at 1200C for 4h in a microwave oven. The reaction mixture was cooled to room temperature, stirred with saturated aqueous KF (3 ml) for 3h, and filtered. The solid was discarded after washing with ethyl acetate (three times). The liquid was poured into H2O and extracted with ethyl acetate. The combined organic layer was washed with H2O and brine, dried over MgSO4, and filtered and the solvent was removed in vacuo. The residue was purified by column chromatography on silica (ethyl acetate/petroleum ether as eluent) to afford the title compound as a white solid (60 mg, 38%). M+ 239.

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; TIBOTEC PHARMACEUTICALS LTD.; MEDIVIR AB; WO2008/96002; (2008); A1;,
Bromide – Wikipedia,
bromide – Wiktionary