Tag: M.W=200-300

937046-98-5, name is 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine, 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. Quality Control of 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine

To a dry, argon purged round bottom flask (100 mL) were added 7-bromo-pyrrolo[2,1-f][1,2,4]triazin-4-ylamine (234 mg, 1.10 mmol) (prepared according to WO2007056170) and anhydrous THF (1.5 mL). TMSCl (276:L, 2.2 mmol) was then added and the reaction mixture stirred for 2 hours. The flask was placed into a dry ice/acetone bath (-78 C.) and BuLi (2.5 mL, 4.0 mmol, 1.6M in hexanes) was added dropwise. After 1 hour, a solution of compound 406 (432.5 mg, 1.0 mmol) in THF was cooled to 0 C. and then added to the reaction flask dropwise. After 1 hour of stirring at -78 C., the flask was warmed to 0 C. and sat. NH4Cl (5 mL) was added to quench the reaction. The organics were extracted using EtOAc (3×10 mL) and the combined organic layers were dried using MgSO4. The solvent was removed under reduced pressure and the crude material was purified using flash chromatography (hexanes/EtOAc). 560 mg (90%) of compound 407 was isolated as a mixture of two anomers. LC/MS=567.2 (M+H+). 1H NMR (300 MHz, CDCl3): * 7.85 (m, 1H), 7.27 (m, 15H), 7.01 (m, 1H), 6.51 (m, 1H), 4.66 (m, 8H), 4.40 (m, 2H), 3.79 (m, 3H), 1.62 (s, 2?-CH3 from the one anomer), 1.18 (s, 2?-CH3 from the other anomer).

The synthetic route of 937046-98-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GILEAD SCIENCES, INC.; Delaney, William E.; Link, John O.; Mo, Hongmei; Oldach, David W.; Ray, Adrian S.; Watkins, William J.; Yang, Cheng Yong; Zhong, Weidong; US2013/273005; (2013); A1;,
Bromide – Wikipedia,
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16518-62-0, name is 3-Bromo-N,N-dimethylaniline, 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. HPLC of Formula: C8H10BrN

General procedure: Bromo-N,N-dimethylaniline (400 mg, 2.0 mmol), (trimethylsilyl)acetylene (236 mg, 2.4 mmol), Pd(PPh3)4 (116 mg, 0.1 mmol), CuI (19mg, 0.1 mmol), diisopropylamine (5 mL) and toluene (15 mL) wereadded to a flask and the mixture was stirred at 80 C overnight. Thenthe reaction mixture was poured into saturated NH4Cl (50 mL) andextracted with CH2Cl2 (3 x 20 mL), the organic layer was washed withsaturated brine (1 x 50 mL) and dried over MgSO4. After filtration,solvents were removed by rotary evaporation (40-45 C ). The crudeproduct was subjected to column chromatography (SiO2; eluent,hexane/ CH2Cl2, 3:1) to give the corresponding compounds. N,N-Dimethyl-3-[(trimethylsilyl)ethynyl]aniline (3b): Pale yellow oil; yield 84%.

The synthetic route of 16518-62-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Fang, Jing-Kun; Sun, Tengxiao; Fang, Yu; Xu, Zhimin; Zou, Hui; Liu, Yuan; Ge, Fangting; Journal of Chemical Research; vol. 39; 8; (2015); p. 487 – 491;,
Bromide – Wikipedia,
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Synthetic Route of 156682-52-9,Some common heterocyclic compound, 156682-52-9, name is 1,4-Dibromo-2,3-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.

-PrMgCl-LiCl (2 M, 2.03 mL) at -40C was added to a solution of Compound BD4-3 (0292) (1.00 g, 3.68 mmol) in THF (20.00 mL) at -40C. The mixture was stirred at -40C for 1 hour and again stirred at -7C for another 1 hour. The mixture was then cooled to -30C. DMF (349.66 mg, 4.78 mmol) at -23C was added in one portion. The mixture was stirred while keeping a temperature range of -25C to 15C for 3.5 hour. TLC indicated when the reaction was completed. The reaction mixture was poured into H2SO4 (100 mL, 1M) cooled to 0C by ice bath, and then the resulting mixture was extracted with EtOAc (20 mL * 3). The combined organic layers of the reaction mixture were washed with brine (30 mL * 3), dried over Na2SC>4, filtered and concentrated under reduced pressure to afford Compound BD4-4 (800.00 mg, crude) as a yellow solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,4-Dibromo-2,3-difluorobenzene, its application will become more common.

Reference:
Patent; THE BROAD INSTITUTE, INC.; VACCA, Joseph, P.; (103 pag.)WO2018/75871; (2018); A1;,
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Synthetic Route of 101417-40-7, 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. 101417-40-7 name is 4-(Bromomethyl)benzo[d][1,3]dioxole, 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.

5.8 g (0.025 mol) of Va, 3.3 g (0.027 mol) of p-hydroxybenzaldehyde,10.2 g (0.076 mol) of potassium carbonate and 1 g of potassium iodide were added to 40 ml of acetone and the reaction was refluxed overnight.Stop the reaction, filter, evaporate the solvent under reduced pressure, add ethyl acetate and water, and separate the liquid.The aqueous phase was extracted with ethyl acetate and the organic phases were combined, washed with saturated brine and dried over anhydrous sodium sulfate for 8 hours.The desiccant was filtered off, the solvent was evaporated under reduced pressure, and the residue was separated by silica gel column chromatography.Elution with petroleum ether:ethyl acetate (10:1) to collect the desired components,VIb white solid 5.1g, yield 78.2%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-(Bromomethyl)benzo[d][1,3]dioxole, and friends who are interested can also refer to it.

Reference:
Patent; The Chinese People’s Liberation Army Military Academy Of Medical Sciences Poison Pharmaceutical Institute; Zhong Bohua; Zhang Ping; He Xinhua; Shi Weiguo; Fan Shiyong; Yao Yishan; Jia Hongxin; (20 pag.)CN103804341; (2018); B;,
Bromide – Wikipedia,
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Reference of 75024-22-5, These common heterocyclic compound, 75024-22-5, name is 1,4-Dibromo-2,3-dimethylbenzene, 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.

Add 6.3 mmol to a 100 ml three-necked flask under N2 protection.1,4-Dibromo-2,3-dimethylbenzene, 13.5 mmol 3,5-dimethylphenylboronic acid25.6mmol potassium carbonate, 0.2mmol tetrakistriphenylphosphine palladium,30 ml of 1,4-dioxane, 6 ml of deionized water, and then replaced with nitrogen three times.Then, it was heated to 90 C with an oil bath under magnetic stirring for 6 h. After the reaction,After washing with water, extracting, drying, and removing the organic solvent under reduced pressure,The product was isolated by column chromatography (petroleum ether), yield 88%.1.9 mmol of the obtained product, 68 mmol of potassium permanganate, 10 ml of pyridine,12 ml of distilled water was added to a 100 ml three-necked flask, and then heated to 100 C with an oil bath under magnetic stirring, and the reaction was refluxed for 15 hours. After the reaction was completed, the organic solvent was depressurized under reduced pressure, and then water was added thereto. After ultrasonic etching, MnO 2 was filtered through celite.Adding hydrochloric acid to adjust the pH to 1 can precipitate a large amount of white powder, collect by centrifugation and dry.The polycarboxylic acid product was obtained in a yield of 94%.Finally, 1.8 mmol of hexacarboxylic acid product, 4 mmol of hydroxylamine hydrochloride,10 ml of pyridine was added to a 50 ml single-necked flask and heated to 90 C with an oil bath under magnetic stirring.Reaction for 6 h. After the reaction, the organic solvent was depressurized under reduced pressure, and then diluted with hydrochloric acid for a while, collected by centrifugation and dried to obtain an off-white product b with a yield of 97%.

Statistics shows that 1,4-Dibromo-2,3-dimethylbenzene is playing an increasingly important role. we look forward to future research findings about 75024-22-5.

Reference:
Patent; Tongji University; Li Liangchun; Liang Gan; Sun Chengmei; (12 pag.)CN109608381; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 1435-52-5, 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. 1435-52-5, name is 1,4-Dibromo-2-fluorobenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

150ml three-necked flask, Add 0.01 mol of 2,5-dibromofluorobenzene, 0.012 mol of M5, 0.02 mol of sodium carbonate and 10 ml of ethylene glycol dimethyl ether, It was purged with nitrogen, heated to 190 ° C, and stirred 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. Filtration, the filtrate is steamed, passed through a silica gel column, Obtaining a white intermediate 7a, The purity was 98.10percent, and the yield was 70.5percent.

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, 1,4-Dibromo-2-fluorobenzene, other downstream synthetic routes, hurry up and to see.

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

Electric Literature of 699-03-6,Some common heterocyclic compound, 699-03-6, name is 1-(4-Bromophenyl)-N-methylmethanamine, molecular formula is C8H10BrN, 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.

A mixture of l-(4-bromophenyl)-N-methylmethanamine (2 g, 10 mmol, 1.0 eq), TEA (3 g, 30 mmol, 3 eq) was cooled to 0 C. Then acetyl chloride (942 mg, 12 mmol, 1.2 eq) in DCM (20 mL) was added. The mixture was stirred at rt for 1 h. The mixture was washed with brine,dried over Na2SO i, filtered and concentrated. The residue was purified on silica gel column (PE/EtOAc = 5/1) to give N-(4-bromobenzyl)-N-methylacetamide as a yellow oil (1.6 g, 67%).

The synthetic route of 699-03-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LIFESCI PHARMACEUTICALS, INC.; MCDONALD, Andrew; WO2015/103317; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 1074-24-4, name is 1,4-Dibromo-2,5-dimethylbenzene, 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 1074-24-4, Computed Properties of C8H8Br2

1,4-dibromo-2,5-dimethylbenzene: 1H-1,2,4-triazole: potassium carbonate: cupric oxide molar ratio is 2:10:30:1In a 50 ml three-necked round-bottom flask equipped with magnetic stirrer, reflux condenser and thermometer, add CuO (0.0398 mg, 0 . 5mmol), potassium carbonate (2.0731g, 15mmol), 1H-1,2,4-triazole (0.345 mg, 5mmol), 1,4-dibromo-2,5-dimethylbenzene (0.3360g, 1mmol), 20mL DMF. Start stirring at 100 deg.C. React for 24 hours. After the reaction, the reaction liquid to room temperature, filtered, the filtrate by adding 100 ml water, precipitating a large amount of precipitation, filtration, collection filter cake, the yield is 60percent.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,4-Dibromo-2,5-dimethylbenzene, and friends who are interested can also refer to it.

Reference:
Patent; Tianjin Normal University; Wang, Ying; (12 pag.)CN105669719; (2016); A;,
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 69321-60-4 as follows. name: 2,6-Dibromotoluene

To the solution of 2,6-dibromotoluene (55.5 g, 222.1 mmol) and NBS (43.5 g, 244.3 mmol) in carbon tetrachloride (300 mL) was added benzoyl peroxide (5.37 g, 22.2 mmol). The reaction mixture was refluxed for 20 h, cooled to room temperature, washed with water (300 mL×3) and brine (300 mL) and dried over anhydrous sodium sulfate. The solution was filtered and evaporated to give 1,3-dibromo-2-bromomethylbenzene as a yellow power (71 g). This material was used for next step without further purification.

According to the analysis of related databases, 69321-60-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Billedeau, Roland Joseph; Kondru, Rama K.; Lopez-Tapia, Francisco Javier; Lou, Yan; Owens, Timothy D.; Qian, Yimin; So, Sung-Sau; Thakkar, Kshitij C.; Wanner, Jutta; US2012/295885; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 40161-54-4, name is 1-Bromo-2-fluoro-4-(trifluoromethyl)benzene, molecular formula is C7H3BrF4, 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. Application In Synthesis of 1-Bromo-2-fluoro-4-(trifluoromethyl)benzene

Reference Example 54 1-[2-fluoro-4-(trifluoromethyl)phenyl]pyrrolidin-3-ol; A solution of 1-bromo-2-fluoro-4-(trifluoromethyl)benzene (4.6 g), 3-hydroxypyrrolidine (1.5 g), palladium(II) acetate (137 mg), (+/-)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (1.07 g) and cesium carbonate (16.8 g) in toluene (90 mL) was stirred under an argon gas atmosphere at 85C for 16 hr. After cooling to room temperature, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with 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 90:10 – 65:35) to give the title compound (2.82 g, yield 66%) as a gray solid. 1H-NMR (300 MHz, CDCl3) delta:1.63 (d, J = 4.5 Hz, 1 H), 1.96 – 2.22 (m, 2 H), 3.40 – 3.57 (m, 2 H), 3.61 – 3.81 (m, 2 H), 4.51 – 4.66 (m, 1 H), 6.64 (t, J = 9.1 Hz, 1 H), 7.15 – 7.25 (m, 2 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 40161-54-4, its application will become more common.

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