Tag: M.W=100-200

Adding a certain compound to certain chemical reactions, such as: 38573-88-5, name is 1-Bromo-2,3-difluorobenzene, 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 38573-88-5, COA of Formula: C6H3BrF2

To a solution of (3R,4S,8R,9S,10S)-10-[(dimethylamino)methyl]-9-(4- ethynylphenyl)-3,4-dihydroxy-N-(4-methoxyphenyl)-l,6-diazabicyclo[6.2.0]decane-6- carboxamide (Intermediate 35a) (21.60 mg, 45.13 mupiiotaomicron) and l-bromo-2,3-difluorobenzene (8.71 mg, 45.13 muiotaetaomicron, 5.06 L) in CH3CN (500 L) was added Cs2C03 (29.41 mg, 90.26 mutauetaomicron) and XPhos Pd G3 (3.82 mg, 4.51 mutauetaomicron). After stirring with N2 atmosphere at 40C for 1 h, the residue was purified by prep-TLC (Si02, DCM: MeOH = 8: 1) to remove the catalyst and then purified by prep-HPLC(Column: Waters Xbridge Prep OBD C18 150*30 5u; A: water (0.225% formic acid) B: acetonitrile) to give (3S,4R,8R,9S,10S)-9-[4-[2-(2,3- difluorophenyl)ethynyl]phenyl]-10-[(dimethylamino)methyl]-3,4-dihydroxy-N-(4- methoxyphenyl)-l,6-diazabicyclo[6.2.0]decane-6-carboxamide (2.00 mg, 3.14 mupiiotaomicron, 6.96% yield, formic acid salt)) as a white solid. 1H MR (400MHz, CHLOROFORM-d) delta = 8.48 – 8.27 (m, 1H), 7.58 (d, J=7.9 Hz, 2H), 7.40 (d, J=7.9 Hz, 2H), 7.29 (d, J=8.4 Hz, 3H), 7.22 – 7.13 (m, 1H), 7.11 – 7.03 (m, 1H), 6.83 (d, J=8.8 Hz, 2H), 6.73 (br. s., 1H), 3.89 (br. s., 2H), 3.77 (s, 4H), 3.75 – 3.62 (m, 3H), 3.61 – 3.48 (m, 2H), 3.28 (dd, J=6.6, 14.1 Hz, 1H), 2.89 (d, J=12.8 Hz, 3H), 2.80 (d, J=14.6 Hz, 2H), 2.68 (d, J=7.5 Hz, 1H), 2.27 (s, 6H)

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; THE BROAD INSTITUTE, INC.; PRESIDENT AND FELLOWS OF HARVARD COLLEGE; COMER, Eamon; KATO, Nobutaka; MORNINGSTAR, Marshall; MELILLO, Bruno; (154 pag.)WO2018/175385; (2018); A1;,
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Electric Literature of 103-64-0, These common heterocyclic compound, 103-64-0, name is (2-Bromovinyl)benzene, 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.

General procedure: A sealable vial equipped with a magnetic stir bar was charged with Cs2CO3 (325 mg, 1.0 mmol), Cu2O (3.5mg, 0.025 mmol) under a nitrogen atmosphere. The aperture of the vial was then covered with a rubber septum. Under a nitrogen atmosphere, alkyne (1, 0.75 mmol), vinyl halide (6, 0.5 mmol) and DMF (0.5 mL) were added by syringe. The septum was then replaced by a screw cap containing a Teflon-coated septum,and the reaction vessel was placed at 135 C. After stirring at this temperature for 12-24 h, the heterogeneous mixture was cooled to room temperature and diluted with ethyl acetate (20 mL). Theresulting solution was filtered through a pad of silica gel then washed with ethyl acetate (20 mL) and concentrated to give the crude material which was then purified by column chromatography on silica gel to yield enynes 7.

Statistics shows that (2-Bromovinyl)benzene is playing an increasingly important role. we look forward to future research findings about 103-64-0.

Reference:
Article; Tsai, Wan-Ting; Lin, Yun-Yung; Chen, Yi-An; Lee, Chin-Fa; Synlett; vol. 25; 3; (2014); p. 443 – 447;,
Bromide – Wikipedia,
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Some common heterocyclic compound, 556-96-7, name is 1-Bromo-3,5-dimethylbenzene, molecular formula is C8H9Br, 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

General procedure: To an oven-dried test tube equipped with a stir bar were added 0.01 mmol of Pd2(dba)3 and 0.03 mmol of ligand ((R)-Tol-BINAP or BrettPhos). Glove box was used to add 1.5 mmol ofNaOt-Pent and the tube was sealed with a Teflon screw cap. 1 mmol of aromatic halide,1.6 mmol of cyclopropylamine, and 2 mL of toluene were then added to the reaction mixture and heated at 80 C for 18 h. After completion, the reaction mixture was cooled to room temperature, diluted with diethyl ether, filtered over a short pad of silica gel, and concentrated in vacuum. Purification by flash chromatography on silica gel afforded N-cyclopropylaniline.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 556-96-7, its application will become more common.

Reference:
Article; Nguyen, Theresa H.; Maity, Soumitra; Zheng, Nan; Beilstein Journal of Organic Chemistry; vol. 10; (2014); p. 975 – 980;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 59907-13-0, These common heterocyclic compound, 59907-13-0, name is 2-Bromo-1-fluoro-3-methylbenzene, 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.

General procedure: Method A ( Buchwald-Hartwia ) To a mixture of C-1 (1 eq), BB-8 (1.3 eq) and sodium tert-butoxide (2 eq) in toluene (3 to 10 mL/mmol) under N2, was added BINAP (0.2 eq) and Pd2(dba)3 (0.1 eq). The rxn mixture was flushed with N2, heated at a given temperature and stirred for a given time (see Table 25). It was partitioned between water and EtOAc and the org. phase was washed with brine, dried over MgSC>4 and concentrated in vacuo. The crude was purified by CC using Hept/EtOAc. When necessary an additional purification by prep. LC-MS was performed.

Statistics shows that 2-Bromo-1-fluoro-3-methylbenzene is playing an increasingly important role. we look forward to future research findings about 59907-13-0.

Reference:
Patent; IDORSIA PHARMACEUTICALS LTD; FROIDEVAUX, Sylvie; HUBLER, Francis; MURPHY, Mark; RENNEBERG, Dorte; STAMM, Simon; (188 pag.)WO2019/141803; (2019); 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. 556-96-7, name is 1-Bromo-3,5-dimethylbenzene, This compound has unique chemical properties. The synthetic route is as follows., Safety of 1-Bromo-3,5-dimethylbenzene

Preparation 9Preparation of (3,5-dimethyl-phenyl)-pyridin-2-yl-methanol.To a slurry of magnesium turnings (65.7 mg, 2.7 mmol) in THF (10 ml.) was added a crystal of iodine and a few drops of 1-bromo-3,5-dimethyl-benzene. The mixture was stirred at reflux temperature until the brown color started to disappear. The mixture was cooled to 0 0C, and the remaining 1-bromo-3,5-dimethyl-benzene (500 mg, 2.7 mmol) in THF was added dropwise. The reaction mixture was warmed to room temperature and was stirred until the magnesium was consumed. The reaction mixture was cooled to 0 0C, and pyridine-2-carboxaldehyde (289 mg, 2.7 mmol) in THF was added dropwise. The reaction mixture was stirred at room temperature for 30 min. The reaction was quenched with water, and the organic solution was extracted twice with ethyl acetate. The combined organic layers were washed sequentially with water and brine, and dried over MgSO4. The mixture was filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (0 – 50% ethyl acetate in heptane) to afford the title compound (440 mg, 76%). 1H NMR (400 MHz, CDCI3): delta 2.29 (s, 6 H), 5.21 (br s, 1 H), 5.68 (s, 1 H), 6.91 (s, 1 H), 6.98 (br. s, 2 H), 7.16-7.21 (m, 2 H), 7.60-7.63 (m, 1 H), 8.56-8.57 (m, 1 H); MS (ES+): 214.3 (M+1 ).

According to the analysis of related databases, 556-96-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER INC.; CAMERON, Kimberly O’Keefe; PERRY, David Austen; WO2010/67233; (2010); A1;,
Bromide – Wikipedia,
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Application of 17247-58-4, 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 17247-58-4 as follows.

A stirred solution of the ketimime 1a’ (50 g, 187.1 mmol, available from Aldrich Chemical Company, Milwaukee, Wis.) under N2 in dry THF (400 mL) was cooled to -78 C. and treated with 1 M solution of K-tBuO (220 mL, 1.15 equiv.) in THF. The reaction mixture was warmed to 0 C. and stirred for 1 h and treated with bromomethylcyclobutane (28 mL, 249 mmol). The reaction mixture was stirred at room temperature for 48 h and concentrated in vacuo. The residue was dissolved in Et2O (300 mL) and treated with aq. HCl (2 M, 300 mL) The resulting solution was stirred at room temperature for 5 h and extracted with Et2O (1 L). The aqueous layer was made basic to pH 12-14 with aq. NaOH (50%) and extracted with CH2Cl2 (3×300 mL). The combined organic layers were dried (MgSO4), filtered, and concentrated to give pure amine (1b’, 18 g) as a colorless oil.

According to the analysis of related databases, 17247-58-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Schering Corporation; US2006/275366; (2006); A1;,
Bromide – Wikipedia,
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Electric Literature of 111721-75-6, These common heterocyclic compound, 111721-75-6, name is 2-Bromo-3-fluoroaniline, 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.

General procedure: 4-Amino-7-X-8-bromo-N-(alkyl)-cinnoline-3-carboxamide (X = H or F).To a solution of 2-[(3-X-2-bromophenyl)-hydrazono]-N-(alkyl)-2-cyanoacetamide (1.0 equiv) in anhydrous toluene (0.1 M, 1 volume) was added aluminum chloride (3.0 equiv). The reaction was heated with vigorous stirring at 70-90 C for 1-3 h, cooled, and quenched with Rochelle’s salt (saturated aqueous potassium sodium tartrate, 0.5 volume). Afterward, the mixture was stirred at room temperature overnight. The aqueous layer was separated, and the organic layer was treated with fresh Rochelle’ salt (0.5 volume) while stirring at room temperature for 1 h. After separating the resulting layers, the organic suspension was washed with water and filtered to give give a tan solid. Additionally, the organic filtrate was concentrated, and triturated with ether to give a tan precipitate. The resulting solids were filtered to give a tan solid in 30-70% yield of crude product. The combined tan solid was dried at 50 C under high-vacuum to give the title compound, which was used without further purification.The intermediate compounds were prepared as follows:2-[(3-X-2-Bromophenyl)-hydrazono]-N-(alkyl)-2-cyanoacetamide (X = H or F).Solution A: To a mechanically stirred solution of 3-X-2-bromoaniline (1.0 equiv) in acetic acid (2 M, 1 volume) was added water (0.6 volume) at ambient temperature. The mixture was cooled to 0 C, and then concentrated aqueous HCl (0.5 volume) added. A precipitate was formed immediately and the suspension was stirred at 0 C for 20 min. To this suspension was added dropwise a solution of sodium nitrite (1.10 equiv) in water (0.6 volume), maintaining the internal temperature below 5 C. The resulting clear orange solution was stirred at 0 C for another 30 min.Solution B: To a mechanically stirred solution of N-(alkyl)-2-cyanoacetamide (1.25 equiv) in ethanol (4.5 volume) was added a solution of sodium acetate (1.60 equiv) in water (120 volume), and chilled to between 0 C and -5 C.Solution A was poured into solution B, maintaining the internal temperature below 0 C. An orange precipitate was formed gradually. The mixture was stirred below 0 C overnight, and then the orange precipitate was collected by filtration, washed with water (100 mL × 3), and dried at 50 C under high vacuum to remove water. An orange solid was obtained in greater than 95% yield, which was the ‘E’, and used for the next step without further purification.

Statistics shows that 2-Bromo-3-fluoroaniline is playing an increasingly important role. we look forward to future research findings about 111721-75-6.

Reference:
Article; Alhambra, Cristobal; Becker, Chris; Blake, Timothy; Chang, Amy; Damewood Jr., James R.; Daniels, Thalia; Dembofsky, Bruce T.; Gurley, David A.; Hall, James E.; Herzog, Keith J.; Horchler, Carey L.; Ohnmacht, Cyrus J.; Schmiesing, Richard Jon; Dudley, Adam; Ribadeneira, Maria D.; Knappenberger, Katherine S.; MacIag, Carla; Stein, Mark M.; Chopra, Maninder; Liu, Xiaodong F.; Christian, Edward P.; Arriza, Jeffrey L.; Chapdelaine, Marc J.; Bioorganic and Medicinal Chemistry; vol. 19; 9; (2011); p. 2927 – 2938;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 38573-88-5,Some common heterocyclic compound, 38573-88-5, name is 1-Bromo-2,3-difluorobenzene, molecular formula is C6H3BrF2, 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.

To a solution of 2,3-difluorobromobenzene (10.0 g, 51.8 mmol) in dry diethyl ether (120 ml), under nitrogen at -78°C, was added drop wise , n-hexyllithium (2.3 M in hexane, 22.5 ml, 51 .8 mmol). The mixture was stirred for 10 mm after which a solution of tert-butyl 3-formylazetidine-i- carboxylate (12.2 g, 49.2 mmol) in dry diethyl ether (30 ml) was added drop wise. The resultingmixture was stirred at -78°C for 0.5 h and then brought to ambient temperature and stirred for 1 h. Water (50 ml) was added and the mixture was extracted with ethyl acetate (2×50 ml). The combined organic phase was washed with brine, dried (Mg504), filtered and evaporated to dryness. The crude product was purified by flash column chromatography on silica gel (ethyl acetate/isooctane, 0:1 to i:i)to give the title compound (6.55 g). MS mlz (rel. intensity, 70 eV)299 (M+, 2), 244 (36), 225 (29), 153(99), 57 (bp).

The synthetic route of 38573-88-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; INTEGRATIVE RESEARCH LABORATORIES SWEDEN AB; PETTERSSON, Fredrik; SONESSON, Clas; (79 pag.)WO2016/185032; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 2550-36-9, name is (Bromomethyl)cyclohexane belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C7H13Br

Scheme V, step A: 2-Picoline (5 g, 54 mmol) is dissolved in THF (100 mL) and cooled to -78 C. N-Butyllithium (40 mL of a 1.6M solution in THF, 64.3 mmol) was added to the solution over 10 minutes. The reaction mixture was then warmed to room temperature for 5 minutes and then cooled back down to -78 C. Then cyclohexylmethyl bromide (10 g, 57 mmol) was added, the reaction was warmed to room temperature and allowed to stir overnight. The reaction was then heated at reflux for 6 hours and then cooled to room temperature. The solvent was removed under vacuum and water and ethyl acetate were then added to the residue. The layers were separated and the aqueous was extracted with ethyl acetate. The organic extracts were combined, dried over anhydrous magnesium sulfate, filtered and concentrated to provide a dark oil. The oil was purified by flash chromatography to provide 2-pyridyl-1-cyclohexylethane (9 g, 89%).

The synthetic route of 2550-36-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Eli Lilly and Company; US6828332; (2004); B1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 58534-95-5, name is 3-Bromo-2-fluoroaniline, 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 58534-95-5, SDS of cas: 58534-95-5

A mixture of 3-bromo-2-fluoroaniline (111, 10 g), (3-chloropyridin-2-yl)boronic acid (121, 20 g), K2CO3 (30 g) and Pd(dppf Cl2 (6.42 g) in solvent (dioxane 130 mL, H2O 33 mL) was purged with argon in a pressure vessel for 5 min and stirred for 15 h at 100 C. The solvent was removed under reduced pressure and the residue was purified by flash column chromatography over silica gel. The purified material was then dissolved in MeOH and treated with HCl/MeOH. The solvent was removed and the solid was washed with IPA-heptane (1/1) to afford 3-(3-chloropyridin-2-yl)-2-fluoroaniline hydrochloride (122).

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

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; (337 pag.)WO2017/35349; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary