Tag: M.W=200-300

Application of 337915-79-4, A common heterocyclic compound, 337915-79-4, name is 5-Bromo-N1-methylbenzene-1,2-diamine, molecular formula is C7H9BrN2, 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.

Intermediate XI6-Bromo-1,2-dimethyl-1H-benzoimidazole A solution of 4-bromo-2-methylamino-aniline (1.10 g) in acetic acid (15 mL) was stirred at 130 C. for 2 h. After cooling to ambient temperature, the solution was concentrated under reduced pressure and the residue was taken up in ethyl acetate. The resulting solution was washed with 10% aqueous K2CO3 solution and brine and dried (MgSO4). The solvent was removed and the remainder was purified by chromatography on silica gel (CH2Cl2/MeOH/NH4OH 99:1:0.1->9:1:0.1) to give the title compound as a solid.Yield: 0.58 g (47% of theory); Mass spectrum (ESI+): m/z=225/227 (Br) [M+H]+.

The synthetic route of 337915-79-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VITAE PHARMACEUTICALS, INC.; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2012/108578; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 4263-52-9, name is Sodium 2-bromoethanesulphonate, 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 4263-52-9, Safety of Sodium 2-bromoethanesulphonate

EXAMPLE 2 Production of Disodium 2,2′-dithiobis Ethane Sulfonate To a mixture of 50.1 g of water with 24.4 g of thioacetic acid, 50.7 g of 25% aqueous sodium hydroxide solution were added dropwise at 10-30 C. This solution was added dropwise to a solution of 63.3 g of sodium 2-bromoethane sulfonate and 70 g of water at 50-70 C. and allowed to react at 80-90 C. for 2 hours. Thereto 54.2 g of 25% aqueous sodium hydroxide solution were added and allowed to react at refluxing temperature (about 105 C.) until the end of the reaction was confirmed by HPLC. After addition of 3.25 g of acetic acid, the reaction mixture was refluxed for 6 hours and then cooled to about 30 C. The pH of the mixture was adjusted to 7.3 with 25% sodium hydroxide solution. Oxygen was allowed to react with 260 mL of aqueous sodium 2-mercapto ethane sulfonate solution obtained above at about 30 C. and 0.5-0.6 MPa of oxygen pressure. When the end of the reaction was confirmed by HPLC, the reaction was stopped and the mixture was neutralized with acetic acid. The mixture was heated to about 70 C. and it was observed that the mixture had been dissolved. After that, the mixture was filtered with a filtering assistant agent (radiolite) and the filtering assistant agent was washed with 10 g of water. The mixture was concentrated under reduced pressure (about 10 kPa) at 70 C. When the amount of the distilled out water became 60 g, the concentration was stopped and it was observed that the mixture remained dissolved at about 75 C. Cooling the mixture, crystallization began at 60+-5 C. After aging for about 30 minutes, the mixture was cooled to 25 C. and the crystals were aged for 2 hours at 25 C. The crystals were filtered out and washed with 24 g of water being cooled to 2 C. and then 48 mL of 70% aqueous ethanol solution. Drying the crystals at about 70 C. afforded 39.1 g of substantially pure disodium 2,2′-dithiobis ethane sulfonate crystals. The yield was 77.6% after crystallization. The purity of the product was 99.4%. According to the present invention, compounds of Formula II, such as disodium 2,2′-dithiobis ethane sulfonate, can be produced by an efficient procedure from available, relatively less expensive raw compounds in good yield with high purity. The above details are not limitative of the invention, which is defined by the scope of the following claims. It will be appreciated by those skilled in the art that changes could be made to the embodiments described above without departing from the broad inventive concept thereof. It is understood, therefore, that this invention is not limited to the particular embodiments disclosed, but it is intended to cover modifications within the spirit and scope of the present invention as defined by the appended claims.

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; BioNumerik Pharmaceuticals, Inc.; US2005/137419; (2005); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 3638-73-1, 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. 3638-73-1, name is 2,5-Dibromoaniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

3. Synthesis of 2,5-dibromophenol; Sodium nitrite (65.2 mmol) was added in several portions to a solution of 2,5-dibromobenzenamine (55.8 mmol) in trifluoroacetic acid (80 mL) at 0 C. The resulting solution was added to a boiling solution of sodium sulfate (10 g) in 50% sulfuric acid (120 mL) and the reaction mixture was maintained at reflux for 1 h. Then the product was steam-distilled and the distillate was extracted with dichloromethane (2¡Á200 mL). The combined organic layers were dried (sodium sulfate) and concentrated to provide 2,5-dibromophenol in 41% yield as a yellow 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, 2,5-Dibromoaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Memory Pharmaceuticals Corporation; US2010/16297; (2010); 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. 64695-79-0, name is 2-Bromo-4,5-difluoroaniline, This compound has unique chemical properties. The synthetic route is as follows., Formula: C6H4BrF2N

To a solution of 2-bromo-4,5- difluoroaniline (1.2 g, 4.3 mmol) in DMF (4 mL) was added tetrakis(triphenylphosphine)palladium(0) (400 mg, 0.34 mmol) and zinc cyanide (800 mg, 6.8 mmol). The solution was sparged with nitrogen and heated at 120 C for 30 minutes in a Biotage microwave reactor. The resulting suspension was filtered and concentrated in vacuo to afford the crude product. Purification by column chromatography (CI 8 reverse phase, water + 0.1% NH3 H20 -> MeCN + 0.1% NH3 H2O) afforded the desired 2-Amino-4,5-difluorobenzonitrile.

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 64695-79-0.

Reference:
Patent; INCEPTION 1, INC.; JACINTHO, Jason, Duarte; CLARK, Ryan, Christopher; SHENG, Tao; OBALLA, Renata, Marcella; STOCK, Nicholas, Simon; ROPPE, Jeffrey, Roger; (161 pag.)WO2017/192304; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 54962-75-3, 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 54962-75-3 as follows.

3-(4-MetIzyI-1H-imidazo1-1-y1)5-(trifluorornethy1)ani1ine: A suspension of 3-bromo-5-(trifluorornethyl)aniline (4.8 g, 20 mmol), 4-methylimidazole (1.97 g, 24 mmol), potassium carbonate (3.04 g, 22 mmol), Cu (0.57 g, 3 mmol), and 8-hydroxyquinoline (0.44 g, 3 mrnol,) in dry DMSO (20 mL) in a pressure tube was degassed by bubbling N2 into the suspension for 10minutes while stirring. The tube was sealed tightly. The mixture was heated at 120 C (oil bath temperature) for 15 h. The mixture was cooled down to 45- 50C and 14% aq. NH4OH (20 mL) was added. The mixture was maintained at this temperature for I h. After cooling to rt, water and ethyl acetate were added. The aqueous layer was extracted with ethyl acetate and the combined organic layers were passed through a short silica gel column to remove most of green/blue Cusalts. The filtrate was dried over sodium sulfate and concentrated on a rotavap. The crude product was recrystallized from EtOAc/hexanes, giving pure pale yellow needles. The motherliquor was concentrated and the residue was purified on silica gel column (5% methanol/methylene chloride), yielding a second crop as pale yellow needles.

According to the analysis of related databases, 54962-75-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARIAD PHARMACEUTICALS, INC.; GOZGIT, Joseph, M.; RIVERA, Victor, M.; SHAKESPEARE, William, C.; ZHU, Xiaotian; DALGARNO, David, C.; WO2013/162727; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 876-53-9, 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 876-53-9 as follows.

General procedure: A solution of 43 g (0.2 mol) of 1-bromoadamantane in 260 mL of methylene chloride was cooled to -10 C, and 61.9 g (0.23 mol) of aluminum bromide was added. The mixture was stirred for 0.5 h, 44 mL (40 g, 0.42 mol) of isopropenyl acetate was added over a period of 2 h, and the mixture was stirred for 0.5 h, poured onto 200 g of ice, and made weakly alkaline reaction by adding sodium carbonate (106 g, 1 mol) and sodium metabisulfite (38 g, 0.2 mol). The organic layer was separated, and the aqueous layer was extracted with methylene chloride (3 ¡Á 50 mL). The extracts were combined with the organic phase, the solvent was distilled off, and the residue was distilled under reduced pressure. Yield 31.9 g (83%), bp 110-112 C (4 mm). 1H NMR spectrum (DMSO-d6), delta, ppm: 1.50-1.80 m (12H, CH2), 1.94 s (3H, CH), 2.10 s (3H, CH3), 2.16 s (2H, CH2CO).

According to the analysis of related databases, 876-53-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Novakov; Orlinson; Savel?ev; Potaenkova; Vostrikova; Tarakanov; Nakhod; Russian Journal of General Chemistry; vol. 87; 12; (2017); p. 2762 – 2765; Zh. Obshch. Khim.; vol. 87; 12; (2017); p. 1942 – 1946,5;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 393-37-3, 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. 393-37-3, name is 5-Bromo-2-fluorobenzotrifluoride belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Reference Example 53 1-[4-fluoro-3-(trifluoromethyl)phenyl]pyrrolidin-3-ol; A solution of 4-bromo-1-fluoro-2-(trifluoromethyl)benzene (10 g), 3-hydroxypyrrolidine (3.56 g), palladium(II) acetate (462 mg), (+/-)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (2.57 g) and cesium carbonate (26.8 g) in toluene (220 mL) was stirred under an argon gas atmosphere at 90C for 16 hr. After cooling to room temperature, the reaction mixture was filtered through celite, and the celite was washed with ethyl acetate. The filtrate and washing were combined and the solution was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate 80:20 – 25:75) to give the title compound (5.91 g, yield 58%) as a pale-yellow oil. 1H-NMR (300 MHz, CDCl3) delta:1.72 (d, J = 3.4 Hz, 1 H), 2.00 – 2.29 (m, 2 H), 3.25 (d, J = 10.2 Hz, 1 H), 3.33 (td, J = 8.8, 3.6 Hz, 1 H), 3.40 – 3.59 (m, 2 H), 4.63 (br. s, 1 H), 6.54 – 6.70 (m, 2 H), 7.05 (t, J = 9.4 Hz, 1 H).

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

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2295406; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 327-51-5,Some common heterocyclic compound, 327-51-5, name is 1,4-Dibromo-2,5-difluorobenzene, molecular formula is C6H2Br2F2, 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.

(1019) (1020) intermediate 31-1 (1021) [00354] Into a 100-mL round-bottom flask that purged and maintained under an inert atmosphere of nitrogen was added 4-bromo-2-chloro-l-iodobenzene (1.20 g, 3.78 mmol), benzyl piperazine-l -carboxylate (0.924 g, 4, 19 mmol), NaOtBu (1.10 g, 1 1.4 mmol), XantPhos (0.695 g, 1.20 mmol), Pd2(dba)3 (0.393 g, 0.430 mmol), and toluene (10 mL). The reaction mixture was stirred for 4 h at 60 C and then concentrated in vacuo to provide a crude product that was purified by FCC eluting with ethyl acetate/petroleum ether (1 : 10) to afford benzyl 4-(4-bromo-2- chlorophenyl)piperazine-l -carboxylate as a colorless oil (713 mg, 46%). LCMS (ESI, m/z) 409, 41 1 [ M 1 [ j .

The synthetic route of 327-51-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FORMA THERAPEUTICS, INC.; GUERIN, David Joseph; BAIR, Kenneth W.; CARAVELLA, Justin A.; IOANNIDIS, Stephanos; LANCIA JR., David R.; LI, Hongbin; MISCHKE, Steven; NG, Pui Yee; RICHARD, David; SCHILLER, Shawn E. R.; SHELEKHIN, Tatiana; WANG, Zhongguo; (365 pag.)WO2017/139778; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 58971-11-2, These common heterocyclic compound, 58971-11-2, name is 3-Bromophenethylamine, 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.

Example 20A: 2-(trimethylsilyl)ethyl 3 -bromophenethylcarbamate 1003351 2-(3-Bromophenyl)ethanamine (1 g, 5.00 mmol) and 2-(trimethylsilyl)ethylp-nitrophenyl carbonate (1.416 g, 5.00 mmol) were dissolved in MeOH (40.0 mL). DIPEA (1.048 mL, 6.00 mmol) was added, and the reaction was allowed to stir overnight. The reaction was concentrated in vacuo. The crude material was purified by silica gel column chromatography (0 to 100% EtOAc in hexanes) to yield Example 20A (1.61 g, 94%) 1H NMR (400 MHz, CHLOROFORM-cl) oe ppm 7.30 – 7.35 (2 H, m), 7.14 (1 H, t,J=7.53 Hz), 7.06-7.11 (1 H, m), 4.60(1 H, br. s.), 4.07-4.15 (2 H, m), 3.38 (2 H, q, J=6.61 Hz), 2.75 (2 H, t, J=6.78 Hz), 0.89 – 0.99 (2 H, m), 0.00 (9 H, s).

The synthetic route of 58971-11-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; RICHTER, Jeremy; BATES, J. Alex; CHENEY, Daniel L.; WO2014/201073; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 2862-39-7, 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. 2862-39-7 name is 2-Bromo-N,N-dimethylethanamine 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.

General procedure: Example 54A 3-Ethyl-5-methyl-1-(2,2,2-trifluoroethyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione 1.0 g (4.76 mmol) of the compound from Ex. 42A and 2.32 g (7.13 mmol) of caesium carbonate were stirred in 12 ml of anhydrous DMF at RT for 10 min, before 700 mul (7.13 mmol) of 1,1,1-trifluoro-2-iodoethane were added. Then the reaction mixture was heated in a microwave oven (Biotage Initiator with dynamic control of irradiation power) to 120 C. for 4 h. After cooling to RT, the mixture was diluted with ethyl acetate and washed successively with water and saturated sodium chloride solution. After drying over anhydrous magnesium sulphate, the mixture was filtered and concentrated to dryness. The residue obtained was purified by MPLC (Biotage cartridge, 100 g of silica gel, cyclohexane/ethyl acetate 3:1). After combination of the product fractions, concentration and drying under high vacuum, 592 mg (42% of theory) of the title compound were obtained. 1H-NMR (400 MHz, DMSO-d6, delta/ppm): 10.09 (s, 1H), 4.00 (t, 2H), 3.91 (q, 2H), 2.79 (s, 3H), 2.58 (t, 2H), 2.20 (s, 6H), 1.13 (t, 3H). LC/MS (Method 1, ESIpos): Rt=0.39 min, m/z=310 [M+H]+.

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

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; HAeRTER, Michael; KOSEMUND, Dirk; DELBECK, Martina; KALTHOF, Bernd; WASNAIRE, Pierre; SUessMEIER, Frank; LUSTIG, Klemens; (369 pag.)US2018/65981; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary