Month: May 2021

Adding a certain compound to certain chemical reactions, such as: 5910-12-3, name is 3-Bromopyrazolo[1,5-a]pyridine, 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 5910-12-3, SDS of cas: 5910-12-3

Part B begins with commercially available bromo-pyrazolopyrimidine 47 (755 mg, 3.83 mmol) and 4,4,5,5-tetramethyl-2-(propan-2-yloxy)-l,3)2-dioxaborolane (2.3 mL, 11.50 mmol) in THF (1.5 mL) at -78 0C. To this solution was added n-butyllithium (4.8 mL, 7.66 mmol) dropwise over 10 minutes. The reaction was slowly warmed to room temperature and was poured into water (10 mL) and partitioned with dichloromethane (10 mL). The organic was dried over sodium sulfate and concentrated before purification by column chromatography (0- 20% ethyl acetate in hexanes) to yield the boronic ester 48 (18% yield, 170 mg). 1H NMR (500 MHz, cdcl3) delta 8.54 – 8.44 (m, OH), 8.03 (s, 1 H), 7.65 (s, 1 H), 7.62 (d, J – 8.8, 1 H), 6.89 (d, J – 7.2, 1 H), 6.72 (x, J ‘ 54.4, 1 H), 6.20 (d, J = 9.3, 1 H), 4.37 – 4.06 (m, 1 H), 2.80 (t, J = 9.7, 1 H), 2.31 – 2.20 (m, IH), 2.10 (d, J = 13.7, IH), 1.92 – 1.73 (m, J = 26.0, 13.5, 2H), 1.44 – 1.16 (m, 2H).; Scheme 10.Stop A.Molecules of type 50 were prepared according to scheme 10 with the synthesis of compounds 46 and 48. Compound 46 (step A) was synthesized from commercially available dibromide 44. Regioselective metal-exchange followed by DMF quench provided aldehyde 46. Aldehyde 46 was reacted with excess deoxofluor to furnish compound 46. Preparation of boronic ester 48 (step B) was accomplished from commercial starting material (compound 47) via lithium-halogen exchange in the presence of 4,4,5>5-tetramethyl-2-(propan-2-yloxy)-l,3»2- dioxaborolane. Palladium-mediated coupling of 46 and 48 was followed by saponifcation to yield carboxylic acid 49. Amide formation with intermediate Il and subsequent deprotection provided compound 50.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Bromopyrazolo[1,5-a]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; MERCK & CO., INC.; KATZ, Jason; KNOWLES, Sandra, L.; JEWELL, James, P.; SLOMAN, David, L.; STANTON, Matthew, G.; NOUCTI, Njamkou; WO2010/17046; (2010); 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. 5279-32-3, name is 5,6-Dibromobenzo[d][1,3]dioxole, A new synthetic method of this compound is introduced below., name: 5,6-Dibromobenzo[d][1,3]dioxole

Step 1 Preparation of 5-bromo-6-(4-fluorophenyl)-1,3-benzodioxole Under nitrogen, 1.1 g of Pd(PPh3)4 was added to a stirred solution of 10.4 g (37.2 mmol) of 5,6-dibromo-1,3-benzodioxole and 2.6 g (18.6 mmol) of 4-fluorophenylboronic acid in 100 mL of toluene, 60 mL of ethanol, and 40 mL of M Na2 CO3. After vigorous stirring at reflux overnight, the solvent was removed in vacuo. The residue was dissolved in ethyl acetate, washed with water, and dried over Na2 SO4. Purification by silica gel chromatography (Waters Prep-500A) with hexane as the eluent gave 3.9 g (71%) of 5-bromo-6 (4-fluorophenyl)-1,3-benzodioxole as a colorless solid: mp 86.0-87.5 C.; NMR (CDCl3) delta 6.02 (s, H), 6.77 (s, 1H), 7.04-7.13 (m, 3H), 7.28-7.35 (m, 2H).

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; G.D. Searle & Co.; US5739166; (1998); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 1268954-77-3, 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. 1268954-77-3, name is 1-(4′-Bromo-[1,1′-biphenyl]-3-yl)naphthalene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Into a 200-mL four-necked flask were introduced the compound 8 (5.0 g; 615.0 mmol), the compound 7 (4.8 g; 13.5 mmol), NaOtBu (4.88 g; 50 mmol), and 100 mL of toluene. Nitrogen bubbling was conducted for 30 minutes (solution A). On the other hand, tri-t-butylphosphine (121 mg) was added to a toluene solution (6 mL) of a tris(dibenzylideneacetone)dipalladium chloroform complex (77 mg), and the mixture was heated to 65C (solution B). In a nitrogen stream, solution B was added to solution A, and this mixture was reacted with heating and refluxing for 4 hours. The organic layer was washed with purified water and dried with magnesium sulfate. Thereafter, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain compound 9 (6.4 g).

The synthetic route of 1-(4′-Bromo-[1,1′-biphenyl]-3-yl)naphthalene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Mitsubishi Chemical Corporation; EP2471772; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 1435-54-7, A common heterocyclic compound, 1435-54-7, name is 1,3-Dibromo-2-fluorobenzene, molecular formula is C6H3Br2F, 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.

Scheme 4-1: In Step 1 the appropriately substituted dibromo species is coupled with an appropriate boronic acid as known in the art to form a mixture of biaryl and triaryl products fromwhich the desired biaryl compound is isolated. In Step 2 the appropriately substituted biaryl species is converted to the Grignard reagent with activated magnesium. In Step 3 the appropriately substituted aldehyde is treated with the previously prepared Grignard reagent to form an alcohol. In Step 4 the appropriately substituted alcohol is converted to a bromide as known in the art with carbon tetrabromide and triphenyl phosphine. In Step 5 the appropriately substituted bromide isconverted to the Grignard reagent with activated magnesium.

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; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; PHADKE, Avinash, S.; DESHPANDE, Milind; AGARWAL, Atul; CHEN, Dawei; GADHACHANDA, Venkat, Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; BARRISH, Joel, Charles; GREENLEE, William; EASTMAN, Kyle, J.; (0 pag.)WO2018/160889; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 261723-28-8, name is (3-Bromo-2-fluorophenyl)methanamine, 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 261723-28-8, category: bromides-buliding-blocks

Example 58 1,1-Dimethylethyl[(3-bromo-2-fluorophenyl)methyl]carbamate To a suspension of [(3-bromo-2-fluorophenyl)methyl]amine (5.0 g, 20.3 mmol) and Na2CO3 (5.5 g, 51.9 mmol) in CH2Cl2 (100 mL), was added dropwise a solution of Boc2O (4.5 g, 20.6 mmol) in CH2Cl2 (10 ml). Then the reaction mixture was stirred overnight at room temperature. After filtration, the solid was washed with CH2Cl2 (50 mL*2), and then the filtrate was washed with water (70 mL*2), brine (70 mL*2) and dried over Na2SO4. After removing the solvent, 5.6 g of 1,1-dimethylethyl[(3-bromo-2-fluorophenyl)methyl]carbamate was obtained (yield: 94%).

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, (3-Bromo-2-fluorophenyl)methanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Glaxo Group Limited; US2009/203657; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 1786-36-3, 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 1786-36-3 as follows.

To a 4 mL vial, N-phenyl-N-(4-piperidyl)propanamide (25.6 mg, 0.11 mmol), K2CO3 (30 mg, 0.22 mmol), KI (9.4 mg, 0.06 mmol) were added with a magnetic stir bar. Acetonitrile (5 ml) was charged to the flask and then (2-bromo-l-fluoroethyl) benzene (37.1 mg, 0.18 mmol) was added. The reaction was allowed to stir at 115 C for 2 days. A sample aliquot was taken from the reaction, diluted with DCM in a microtube, and washed with half-saturated aq. Na2CCb. The organic layer was separated and analyzed by LCMS to confirm reaction completion. The reaction was concentrated under reduced pressure, and the crude material was dissolved in a minimal amount of DCM and dry loaded on celite. The celite/crude material was loaded onto a 10 g column which was connected to a l2 g Cl8 column and purified by reverse phase chromatography (12 g C18; 0-95% MeOH/water) to give S13 as a clear yellow oil (10 mg, 25%). 0.68; LC/MS tR = 1.42 min (Characterization Method A); m/z = 354.85 (M + H); NMR (300 MHz, CD2CI3) d = 7.46 – 7.27 (m, 8 H), 7.12 – 7.04 (m, 2 H), 5.69 – 5.44 (m, 1 H), 4.69 (tt, J = 4.0, 12.2 Hz, 1 H), 3.12 – 2.97 (m, 2 H), 2.87 (ddd, J = 9.3, 14.4, 17.2 Hz, 1 H), 2.64 – 2.43 (m, 1 H), 2.39 – 2.20 (m, 2 H), 1.93 (q, J = 7.4 Hz, 2 H), 1.86 – 1.74 (m, 2 H), 1.58 – 1.37 (m, 2 H), 1.02 (t, J = 7.5 Hz, 3 H).

According to the analysis of related databases, 1786-36-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MARQUETTE UNIVERSITY; DOCKENDORFF, Christopher; ROSAS, Ricardo, Jr.; (0 pag.)WO2020/6563; (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. 1123172-38-2, name is 1-Bromo-3-(tert-butyl)-5-fluorobenzene, A new synthetic method of this compound is introduced below., HPLC of Formula: C10H12BrF

Bromo-3-tert-butyl-5-fluorobenzene (323.2 g, 1.4 moles) was dissolved in THF (3.3 L) and cooled -10 C. iPrMgCl (2M solution in THF, 0.5 eq, 350 mL) was added over 20 min, followed by nBuLi (2.5M solution in hexanes, 1.0 eq, 560 mL) over two hours. DMF (4 eq, 450 mL) was added over one hour then stirred for 45 minutes and quenched with 3M HCl (1000 mL). The layers were separated and the aqueous fraction was diluted with water (1 L) and extracted with ethyl acetate (1 L). The organic fractions were combined and washed with water (2*2 L). The organic fraction was concentrated to provide an orange oil (252 g, quant), used directly in the next reaction.

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; Berthel, Steven; Firooznia, Fariborz; Fishlock, Daniel; Hong, Jun-Bae; Lou, Yan; Lucas, Matthew; Owens, Timothy D.; Sarma, Keshab; Sweeney, Zachary Kevin; Taygerly, Joshua Paul Gergely; US2010/222325; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 268733-18-2, 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. 268733-18-2, name is 4-Bromo-3,5-bis(trifluoromethyl)aniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Disodium phosphate 18.2 g (123 mmol) and tetrabutylammonium hydrogen sulfate 2.1 g (6.20 mmol) were dissolved in a 500 mL solution of acetone and dichloromethane, followed by the addition of 4-bromo-3,5-bis-trifluoromethyl aniline 10.0 g (32.5 mmol) dropwise with a oxone and the reaction solution was stirred for 1 hour at 0 C. Potassium hydroxide was added to maintain the acidity of the reaction solution between 7.5 and 8.5. After completion of the reaction, the solution was diluted with dichloromethane and washed with distilled water several times to remove salts. Magnesium sulfate was then added to the dichloromethane solution and the solvent was filtered then evaporated and the resulting reactant was passed through a silica column pale to give a light yellow compound, 1-bromo-4-nitro-2,6-bis(trifluoromethyl)benzene (8.05 g, 23.8 mmol 73.3% yield). [0103] Melting point: 56-57 C. [0104] 1H NMR (CDCl3, 400 MHz, ppm): 8.71 (s, 2H). [0105] 13C NMR (DMSO-d6, 100 MHz, ppm): 146.62, 132.48 (q, J=31.9 Hz), 126.71 (q, J=5.7 Hz), 125.63, 121.68 (q, J=272.9 Hz).

The synthetic route of 4-Bromo-3,5-bis(trifluoromethyl)aniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kim, Sang Youl; Kim, Sun Dal; Chung, Im Sik; US2015/45481; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 1786-36-3, 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. 1786-36-3, name is (2-Bromo-1-fluoroethyl)benzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Under a nitrogen atmosphere, nickel bromide (4.4 mg, 0.02 mmol),4,4′-dimethyl-2,2′-bipyridine (3.68 mg, 0.02 mmol),Tetrabutylammonium iodide (14.77 mg, 0.04 mmol) manganese powder (43.95 mg, 0.8 mmol),Add solvent NMP (0.5 mL) and stir well. Weigh 4-bromoacetophenone (39.81mg, 0.2mmol) in NMP (0.5mL),After dissolution, add (2-bromo-1-fluoroethyl) benzene (60.92 mg, 0.3 mmol) and mix well.The solution was transferred to a sealed tube. After sealing, the reaction was stirred in an oil bath at 80 C for 24 hours.Cool the reaction to room temperature, ether (5mL)Add an equal volume of saturated ammonium chloride solution to the diluted reaction solution.Filter through a diatomaceous sand core funnel, rinse with a small amount of ether, and collect the filtrate.The filtrate was extracted three times with diethyl ether, and the organic phases were combined (add internal standard dodecane,GC-MS determined crude yield). Dried over anhydrous sodium sulfate,Filtration, distillation to remove the solvent under reduced pressure,After the residue was separated by silica gel column chromatography, the product was weighed.The calculated yield was 39%.

The synthetic route of (2-Bromo-1-fluoroethyl)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sichuan Qing Chemical University; Yang Yi; Luo Gen; Li Youlin; Tong Xia; He Mengmeng; Jiang Yan; Liu Yingle; Shu Yumei; Zheng Yubin; Lu Wenjie; Zhao Yanchuan; (22 pag.)CN110803977; (2020); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 113899-55-1, These common heterocyclic compound, 113899-55-1, name is 1-(2-Bromophenyl)ethylamine, 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 diisopropylethylamine (1.5 g, 12 mmol) to a solution of l-(2-bromo-4- fluoro-phenyl)-ethylamine (4 g, 20 mmol) and di-tert-butyldicarbonate (6.5 g, 30 mmol) in 20 mL of DCM. Stir the mixture overnight at RT. Dilute the mixture with chloroform/IPA (3/1), wash with aqueous saturated sodium chloride and water, dry it over sodium sulfate and concentrate in vacuo. Purify the crude product by column chromatography (10 % methanol in DCM) to give the title compound (2.0 g, 33 %). MS (ES) m/z 244/246 [M-tert-butyl]+.

Statistics shows that 1-(2-Bromophenyl)ethylamine is playing an increasingly important role. we look forward to future research findings about 113899-55-1.

Reference:
Patent; ELI LILLY AND COMPANY; WO2008/144223; (2008); A2;,
Bromide – Wikipedia,
bromide – Wiktionary