Month: August 2021

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

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 1073-06-9, 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. 1073-06-9, name is 1-Bromo-3-fluorobenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example A-3 4-(3-Fluoro-phenyl)-1H-indole To a mixture of 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole (3, 2.43 g, 10 mmol), and 3-bromofluorobenzene (1.09 mL, 10 mmol) in THF (34 mL)) were added Palladium catalyst Pd(PPh3)4 (347 mg, 0.3 mmol) and the freshly prepared sodium hydroxide solution (1.20 g, 30 mmol in 14 mL water). The system was degassed and then charged with nitrogen. The degas procedure was repeated for three times. The mixture was stirred under nitrogen at 70 C. oil bath for 15 hours. TLC showed the completion of the coupling reaction. The mixture was cooled to room temperature, diluted with ethyl acetate, and separated from water layer. The ethyl acetate solution was washed by brine, dried over Na2SO4, and concentrated. The crude product was purified by a silica gel column eluding with hexanes-EtOAc (9:1) to provide 1.88 g (88%) of the product 4-(3-fluoro-phenyl)-1H-indole as a colorless syrup. 1H-NMR (400 MHz, DMSO-d6) delta 11.30 (br s, 1H, NH), 7.52 (m, 2H, aromatic), 7.45 (m, 3H, aromatic), 7.20 (m, 2H, aromatic), 7.12 (m, 1H, aromatic), 6.55 (m, 1H, aromatic). MS m/z 212 [M++1].

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-3-fluorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sugen, Inc.; US2003/69297; (2003); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 134168-97-1, name is 3-Bromo-5-fluoroaniline, molecular formula is C6H5BrFN, 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. category: bromides-buliding-blocks

1000mL 4 neckround bottom flask was charged with 3-bromo-5-fluoroaniline 30.5 g (0.16 mole) and Pd (PPh3) 47.4 g (0.006mole) of potassium carbonate and 88.1 g (0.64 mole) and 1naphthylboronic acid put 32.7 g (0.19 mole), toluene was putinto 210 mL, 160 mL ethanol, 90 mL of water was refluxed for 12 hours. To complete the reaction, and the organic layer wasseparated and the water layer was extracted twice with 100 mL toluene. Formed organic layer was concentrated underreduced pressure and recrystallized with methanol to intermediate a3(27.4 g, 72.1%) was obtained.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 134168-97-1, its application will become more common.

Reference:
Patent; SFC CO., LTD.; KIM, JEONG SOO; RYU, YEON KWON; KO, SANG WON; LEE, SU JIN; KIM, JI HWAN; PARK, JIN JOO; (44 pag.)KR2015/129486; (2015); A;,
Bromide – Wikipedia,
bromide – Wiktionary

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

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,
bromide – Wiktionary

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;,
Bromide – Wikipedia,
bromide – Wiktionary

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,
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 111721-75-6 as follows. Formula: C6H5BrFN

General procedure: Method I. Compounds 1a-1e and 3b were synthesized using a modified procedure.1 Substituted aniline (1.0 equiv.) was added to a round-bottom flask. The flask was fitted with a rubber septum and purged with nitrogen gas, and acetic anhydride (1M in CH2Cl2, 1.1 equiv.) was added at room temperature. The reaction was refluxed overnight and monitored by TLC. Upon completion the reaction mixture was quenched with H2O. The resulting mixture was extracted with CH2Cl2. The combined organic layers were washed with brine, dried over anh. Na2SO4, filtered, then concentrated in vacuo to give the product.

According to the analysis of related databases, 111721-75-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Lasing, Thitiya; Phumee, Atchara; Siriyasatien, Padet; Chitchak, Kantima; Vanalabhpatana, Parichatr; Mak, Kit-Kay; Hee Ng, Chew; Vilaivan, Tirayut; Khotavivattana, Tanatorn; Bioorganic and Medicinal Chemistry; vol. 28; 1; (2020);,
Bromide – Wikipedia,
bromide – Wiktionary

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,
bromide – Wiktionary