Author: Jessica.F

Synthetic Route of 1073-39-8, 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. 1073-39-8, name is 3-Bromobicyclo[4.2.0]octa-1,3,5-triene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a mixture of 3-bromobicyclo[4.2.0]octa-1,3,5-triene (385 mg, 2.10 mmol, 1.20 equiv) in tetrahydrofuran (7 ml) was added n-BuLi (2.5M in hexane, 0.77 ml, 1.10 equiv) dropwise at -78C, and the reaction mixture was stirred for 30 min at -78C. 5-Bromo-2-(dimethylamino)benzaldehyde (400 mg, 1.75 mmol, 1.00 equiv) in tetrahydrofuran (3 ml) was then added to the solution. The reaction mixture was stirred at -78C for 2 h. NH4CI/H20 was added and the mixture was extracted with EtOAc thrice. The combined extracts were washed with brine and dried over Na2S04, then concentrated and purified by chromatography on silica gel (20% EA/PE) to yield bicyclo[4.2.0]octa-1 (6),2,4-trien-3-yl[5-bromo-2- (dimethylamino)phenyl]methanol as a light yellow oil. MS (ES) m/z: 332.0 [M+H]+

The synthetic route of 3-Bromobicyclo[4.2.0]octa-1,3,5-triene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; GAUL, Micheal; KUO, Gee-Hong; XU, Guozhang; LIANG, Yin; (218 pag.)WO2018/89449; (2018); A1;,
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. Application In Synthesis of 2,6-Dibromotoluene

Example 22 5′-[(te/f-butoxycarbonyl-ethyl-amino)-methyl]-4′-methyl-[2,3′]bipyridinyl-4-carboxylic acid methyl esterStep 1 : 2,6-Dibromotoluene (9.8 g, 39 mmol) in THF (300 ml.) was stirred under N2 and was then cooled to -100 0C (ether/liquid N2). n-BuLi (16.4 mL, 41 mmol, 2.5 M in hexane) was then added drop wise and after stirring for 5 minutes DMF (4.5 mL, 58.6 mmol) was added. The reaction was stirred for a further 20 minutes and then for an hour at -78 0C. The reaction was quenched with saturated aqueous NH4CI and allowed to warm up to room temperature. The reaction was diluted with water and the pH adjusted to pH 7-8 with sat. aqueous NaHCO3. The mixture was evaporated in vacuo to remove the THF, and the product was then extracted with Et2O (x3). The combined organic layers were washed with brine and dried (MgSO4). The product was filtered and evaporated on vacuo to give delta-bromo^-methyl-pyridine-S-carbaldehyde as a colourless solid which was used 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; NOVARTIS AG; ASTEX THERAPEUTICS LIMITED; HOWARD, Steven; MORTENSON, Paul Neil; HISCOCK, Steven Douglas; WOOLFORD, Alison Jo-Anne; WOODHEAD, Andrew James; CHESSARI, Gianni; O’REILLY, Marc; CONGREVE, Miles Stuart; DAGOSTIN, Claudio; CHO, Young Shin; YANG, Fan; CHEN, Christine Hiu-Tung; BRAIN, Christopher Thomas; LAGU, Bharat; WANG, Yaping; KIM, Sunkyu; GRIALDES, John; LUZZIO, Michael Joseph; PEREZ, Lawrence Blas; WO2010/125402; (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. 114078-88-5, name is 5-Bromo-1,2,3-triazine, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C3H2BrN3

Compound (M-21) (2.00 g, 12.5 mmol)Was dissolved in chloroform (25.0 mL)4 A molecular sieve (400 mg, powder)And the compound (M-22) (3.10 g, 18.8 mmol) was added at 0 C.,And the mixture was stirred at 0 C. for 5 minutes.After stirring at 45 C. for 40 minutes, it was allowed to cool to room temperature.The solvent was distilled off under reduced pressure,The residue was purified by silica gel column chromatography (n-hexane: ethyl acetate)Compound (M-23)(Yield 1.90 g, yield 67%).

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 114078-88-5.

Reference:
Patent; Kaken Pharmaceutical Co., Ltd.; Watanabe, Atsushi; Sato, Yuki; ogura, Keiji Tamada; Tatsumi, Yoshiyuki; (283 pag.)JP2018/145180; (2018); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 58534-95-5, name is 3-Bromo-2-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. Application In Synthesis of 3-Bromo-2-fluoroaniline

General procedure: GP3-1: A solution of 2-halo substituted aniline (1.0 eq), potassium ethyl xanthate (1.2 eq or 2.2 eq, typically 2.2 eq) In 10 volume of anhydrous DMF was heated at 100 C. or 120 C. for 4 hours under nitrogen. TLC monitored the progress of reaction. After completion, the reaction mixture was cooled to room temperature, diluted with water (10 volume) and neutralized by 1 M HCl solution to pH 5. The formed precipitate was collected by filtration, rinsed with water, firstly dried by rotavapor, and then dried by oil pump to afford 2-mercaptobenzothiazole.; 2-mercapto-7-fluorobenzothiazole The title compound was prepared according to GP3-1 using 2,3-difluoroaniline (3.0 g, 23.5 mmol), potassium ethyl xanthate (8.2 g, 51.0 mmol) and DMF (30 mL). Water was added to precipitate the product as off-white solid. (4.3 g, 100% yield) LC-MS (ESI): [M+1]+=185.77, tR=3.65 min. 1H NMR (400 MHz, d6-DMSO) delta 14.07 (s, 1H), 7.46 (td, J=8.2, 5.6 Hz, 1H), 7.23-7.16 (m, 2H). 13C NMR (101 MHz, d6-DMSO) delta 189.34, 154.34 (d, J=244.5 Hz), 143.52 (d, J=6.6 Hz), 129.13 (d, J=7.8 Hz), 115.67 (d, J=22.9 Hz), 110.14 (d, J=18.7 Hz), 108.94 (d, J=3.4 Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 58534-95-5, its application will become more common.

Reference:
Patent; Wu, Xiao Hua; Wu, Xiaohua; US10221168; (2019); B1;,
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. 937046-98-5, name is 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine, A new synthetic method of this compound is introduced below., Application In Synthesis of 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine

Step 1: 7-(3,6-Dihydro-2H-pyran-4-yl)pyrrolo[2,1-f][1,2,4]triazin-4-amine In a sealed flask a mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-2H-pyran (from Aldrich, 0.64 g, 3.01 mmol), 7-bromopyrrolo[2,1-f][1,2,4]triazin-4-amine (from J & W Pharm Lab, 0.500 g, 2.35 mmol) and N,N-diisopropylethylamine (1.2 mL, 7.0 mmol) in 1,4-dioxane (6 mL) and water (0.32 mL) was stirred together and flushed with N2 for 5 min before bis(tri-t-butylphosphine)palladium (100 mg, 0.24 mmol) was added. The reaction mixture was then sealed and heated at 120 C. for 4 h, filtered through a pad of celite and concentrated. The crude was purified by Biotage silica gel column chromatography (40 g column, 0 to 100% EtOAc in hexanes) to give the desired product as white powders (168.5 mg, 33%). LCMS calcd for C11H13N4O (M+H)+: m/z=217.1. Found: 217.1.

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; Incyte Corporation; Li, Yun-Long; Wang, Xiaozhao; Barbosa, Joseph; Burns, David M.; Feng, Hao; Glenn, Joseph; He, Chunhong; Huang, Taisheng; Mei, Song; Zhuo, Jincong; (169 pag.)US2017/275290; (2017); 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. 937046-98-5, name is 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine, A new synthetic method of this compound is introduced below., category: bromides-buliding-blocks

To a stirred suspension of 7-bromopyrrolo[2,1-f][1,2,4]triazin-4-amine (801 mg, 3.76 mmol), tert-butyl 4-[4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)phenyl]tetrahydro- 1 (2H)-pyrazinecarboxylate (2.19 g, 5.64 mmol), and [1 ,1′-bis(diphenylph?sphino)- ferrocene]dichloro palladium(ll)-complex with dichloromethane (275 mg, 0.38 mmol) in degassed DME (25 mL) was added aqueous Na2CO3 solution (2 M, 5.6 mL). The reaction was heated (80 0C) for 17 h and then cooled to rt. The mixture was filtered through a pad of Celite using ethyl acetate to rinse. The filtrate was washed with water (75 mL), dried (Na2SO4), and concentrated. The crude material was purified by ISCO chromatography using a gradient of 50 to 75% ethyl acetate in hexanes to afford 1.22 g (74%) of the desired product as an off-white solid, which contained trace impurities. 1H NMR (300 MHz, DMSO-de) delta 7.94-7.88 (m, 2 H), 7.86 (s, 1 H), 7.65 (br s, 2 H), 7.03-6.97 (m, 1 H), 6.94 (d, 1H), 6.89 (d, 1 H), 3.51-3.42 (m, 4 H), 3.19-3.11 (m, 4 H), 1.42 (s, 9 H); ES-MS m/z 395.1 [M+H]+, HPLC RT (min) 2.52.

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

Reference:
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2007/56170; (2007); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 2550-36-9, name is (Bromomethyl)cyclohexane, 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 2550-36-9, Recommanded Product: 2550-36-9

The compound prepared in Step 5 (35 mg, 0.08 mmol), (bromomethyl) cyclohexane (21 mg, 0.12 mmol), 2C03 (22 mg, 0.16 mmol), I (2 mg) in DMF (2 mL) was stirred at 90C for 16 hours under N2. The mixture was concentrated, diluted with DCM, washed with brine, dried over Na2S04, filtered and the solvent was evaporated. The residue was purified by prep-HPLC to give pure product (15 mg, yield: 35%).-NMR (400 MHz, CDC13) delta 7.97-7.93 (m, 2H), 7.73 (s, 1H), 7.58 (s, 1 H), 7.52-7.50 (m, 2H), 7.44-7.37 (m, 3H), 7.24-7.16 (m, 2H), 5.84 (s, 1H), 3.18-3.13 (m, 1 H), 2.99-2.97 (m, 4H), 2.95 (s, 3H), 1.74-1.58 (m, 1 H),1.54~1.51 (m, 2H), 1.43-1.41 (m, 2H), 1 .04-0.91 (m, 4H), 0.89-0.79 (m, 2H), 0.76-0.56 (m, 1H). MS (M+H)+: 535.

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; MERCK SHARP & DOHME CORP.; MCCOMAS, Casey, Cameron; LIVERTON, Nigel, J.; SOLL, Richard; LI, Peng; PENG, Xuanjia; WU, Hao; NARJES, Frank; HABERMANN, Joerg; KOCH, Uwe; LIU, Shilan; ISTITUTO DI RICERCHE DI BIOLOGIA MOLECOLARE P. ANGELETTI, SRL; WO2011/106992; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 5433-01-2, These common heterocyclic compound, 5433-01-2, name is 1-Bromo-3-isopropylbenzene, 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 50 Preparation of Ethyl beta-Amino-m-Isopropylcinnamate. To the Grignard reagent prepared from 39.5 g (0.198 mol) of m-bromocumene and 4.9 g (0.20 mol) of magnesium in 150 ml of ether was added 11.2 g (0.099 mol) of ethyl cyanoacetate dropwise with stirring at 10. The mixture was stirred at reflux for 22 hours and was allowed to stand at 23 for four days. Then, 10.6 g (0.20 mol) of NH4 Cl in 60 ml of water was added with stirring at 10-15, followed by 0.20 mol of 2 N, HCl at 0. The layers were separated, and the water layer was extracted with 100 ml of ether. The ether layers were combined, extracted with dilute NaHCO3 solution, dried (CaSO4), and distilled to give 4.95 g of 80% pure product, boiling point 139-142 (0.15 torr) and 0.87 g of about 97% pure product, boiling point 142-143 (0.15 torr). [Infrared analysis of the lower-boiling impurity indicated it to be bi(m-cumenyl)]. Anal. Calc’d. for 97% C14 H19 NO2 -3% C18 H22: C, 72.60; H, 8.24; N, 5.82. Found: C, 72.60; H, 8.46; N, 5.84.

Statistics shows that 1-Bromo-3-isopropylbenzene is playing an increasingly important role. we look forward to future research findings about 5433-01-2.

Reference:
Patent; Monsanto Company; US4187099; (1980); A;,
Bromide – Wikipedia,
bromide – Wiktionary

399-94-0, name is 1-Bromo-2,5-difluorobenzene, 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. category: bromides-buliding-blocks

Referential Example 34: 6-(t-Butyl-diphenylsilyloxy)-1-(2,5-difluorophenyl)-1-hexanol A tetrahydrofuran (30 ml) solution of 1-bromo-2,5-difluorobenzene (0.956 ml, 8.46 mmol) was stirred at -78C. To the reaction mixture was added a hexane solution (6.46 ml, 10.2 mmol) of n-butyl lithium.. The reaction mixture was added to a tetrahydrofuran (20 ml) solution of 6-(t-butyldiphenylsilyloxy)hexanal (2.50 g, 7.05 mmol) at -78C and the mixture was stirred at the same temperature for 30 minutes.. After the temperature of the reaction mixture was elevated to room temperature, diethyl ether was added thereto.. The mixture was washed with a saturated aqueous solution of ammonium chloride and the organic layer was dried over anhydrous sodium sulfate.. After filtration, the filtrate was concentrated under reduced pressure.. The residue was subjected to flash silica gel chromatography, and the fraction obtained from the hexane:ethyl acetate=9:1 elude was concentrated under reduced pressure, whereby the title compound (2.92 g, 4.65 mmol, 88%) was obtained as a colorless oil.1H-NMR (400MHz, CDCl3) delta: 1.04(9H,m), 1.21-1.90(8H,m), 3.64(2H,t,J=6.3Hz), 4.96(1H,t,J=6.5Hz), 6.86-7.01(2H,m), 7.13-7.20(1H,m), 7.32-7.45(6H,m), 7.62-7.70(4H,m).

The synthetic route of 399-94-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP1466898; (2004); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

24358-62-1, name is 1-(4-Bromophenyl)ethylamine, 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. Product Details of 24358-62-1

Propionic anhydride (1.86g) was added to the solution of 1 -(4-bromophenyl)ethylamine (2.38g) and triethylamine (1.45g) in tetrahydrofuran (50ml), and the mixture was stirred at room temperature for 6 hours. The reaction mixture concentrated under reduced pressure, and the residue was purified by silica gel column chromatography to obtain N-[l-(4-bromophenyl)ethyl]propanamide (2.81g).1H-NMR (CDC13) delta: 1.15 (3H, t), 1.46 (3H, d), 2.21 (2H, q), 5.04-5.13 ( 1 H, m), 5.63 (1H, br s), 7.19-7.24 (2H, m), 7.44-7.47 (2H, m).

The synthetic route of 24358-62-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER CROPSCIENCE AG; MURATA, Tetsuya; HATAZAWA, Mamoru; BRUeCHNER, Peter; SHIMOJO, Eiichi; ICHIHARA, Teruyuki; ATAKA, Masashi; SHIBUYA, Katsuhiko; GOeRGENS, Ulrich; WO2011/51455; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary