Tag: M.W=100-200

Application of 656-64-4, 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. 656-64-4, name is 3-Bromo-4-fluoroaniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

4-Amino-N-hydroxy-1,2,5-oxadiazole-3-carboximidoyl chloride 3(3.24 g, 20 mmol) was mixed with water (70 mL) and 3-bromo-4-fluoroaniline (4.18 g, 22 mol, 1.1 equiv). At 60 C, a solution of sodiumbicarbonate (3.36 g, 40 mmol, 2 equiv) in water (15 mL) was added tothe mixture by drops then resulting mixture was heated to reflux. Afterpurification, compound 4 was obtained as a white solid (5.75 g, 91%).1H NMR (300 MHz, DMSO-d6): delta=11.46 (s, 1H), 8.89 (s, 1H), 6.99 (t,J=8.8 Hz, 1H), 6.81 (dd, J1=6.0 Hz, J2=2.7 Hz, 1H), 6.56-6.51 (m,1H), 6.28 (s, 2H) ppm.

The synthetic route of 3-Bromo-4-fluoroaniline has been constantly updated, and we look forward to future research findings.

Reference:
Article; Feng, Xi; Shen, Pei; Wang; Li; Bian, Jinlei; Biochemical Pharmacology; vol. 168; (2019); p. 214 – 223;,
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Related Products of 766-46-1, The chemical industry reduces the impact on the environment during synthesis 766-46-1, name is 2′-Bromophenylacetylene, I believe this compound will play a more active role in future production and life.

General procedure: A THF solution (5.0 mL) of 1 (1.0 mmol) was treated with Bu3SnOMe (1.0 mmol) and t-BuOK (0.5 mmol). The mixture was stirred for 4.5 h under nitrogen at reflux. The reaction mixture was then treated with 3 (207.1 mg, 0.98 mmol), P(t-Bu)3 (0.035 mmol) and Pd2(dba)3 (0.018 mmol) at room temperature, and the mixture was stirred under nitrogen at room temperature for 8 h. After workup with diethylether (3 × 10.0 mL)/NH4Faq (10%, 10.0 mL), the organic layer was dried over MgSO4. After filtration, the solvents were evaporated. The crude product was subjected to column chromatography on silica gel to afford 4a-i. 4a,13 4b,10 4c,14 4d,14 4e,14 4f,14 4g,15 4h14 and 4i14 are known compounds and were identified by their previously reported spectroscopic data.

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, 2′-Bromophenylacetylene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Peng, Li-Fen; Wang, Bing-Hao; Wang, Ming; Tang, Zi-Long; Jiang, Yan-Zi; Jiao, Yin-Chun; Xu, Xin-Hua; Journal of Chemical Research; vol. 42; 5; (2018); p. 235 – 238;,
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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. 21120-91-2, name is 7-Bromobicyclo[4.2.0]octa-1,3,5-triene, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C8H7Br

Step 1. Synthesis of ethyl (acetylamino)(bicyclo[4.2.0]octa-1,3,5-trien-7-yl)cyanoacetate (#99). Sodium (464 mg, 20.2 mmol, 1.2 eq.) was allowed to react with absolute ethanol (40 mL, 0.42 M); to the resulting mixture was added ethyl 2-(acetylamino)-2-cyanoacetate (3.44 g, 20.2 mmol, 1.2 eq.). After 20 minutes at 60 C., 7-bromobicyclo[4.2.0]octa-1,3,5-triene (3.092 g, 16.89 mmol, 1 eq.) was added and the reaction mixture was heated at reflux overnight, then filtered and concentrated in vacuo. The residue was diluted with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo to give a dark oil, which was purified by silica gel chromatography (Gradient: 0% to 50% ethyl acetate in heptane) to give #99 (4.38 g) as a yellow gum. LC-MS: m/z 273.2 [M+H+], retention time=2.36 minutes.

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 21120-91-2.

Reference:
Patent; PFIZER INC.; DOROSKI, Matthew David; MADERNA, Andreas; O’DONNELL, Christopher John; SUBRAMANYAM, Chakrapani; VETELINO, Beth; DUSHIN, Russell George; STROP, Pavel; GRAZIANI, Edmund Idris; US2013/129753; (2013); A1;,
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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. 1003-99-2, name is 2-Bromo-5-fluoroaniline, A new synthetic method of this compound is introduced below., Recommanded Product: 2-Bromo-5-fluoroaniline

Example 29 : 6- (2-Bromo-5-fluoro-phenylamino)-4-cyclopropyl-N- (tetrahydro-pyran-4- ylmethyl)-nicotinamide; A mixture of 6-chloro-4-cyclopropyl-N- (tetrahydro-pyran-4-ylmethyl)-nicotinamide (Description 3) (100 mg), 2-bromo-5-fluoroaniline (65 mg), cesium carbonate (155 mg), tris (dibenzylidene- acetone) palladium (0) (3. 3 mg), 4,5-bis (diphenylphosphino) -9,9-dimethyl xanthene (Xantphos) (2.2 mg) and 1,4-dioxan (1 ml) was stirred under reflux under nitrogen for 18 hours. The mixture was allowed to cool, the insoluble material filtered off, and washed with ethyl acetate. The filtrate was evaporated under reduced pressure and the residue purified by MDAP to afford the title compound as a pale cream solid (14 mg). NMR (DMSO-d6) 8 0.73 (2H, m), 1.02 (2H, m), 1.12-1. 27 (2H, m) 1.62 (2H, d), 1.77 (1H, m), 2.34 (1H, m), 3.13 (2H, t), 3.27 (2H, t), 3.85 (2H, d of d), 6.69 (1H, s), 6.81 (1H, t of d), 7.63 (1H, t), 8.09 (1H, m), 8.11 (1H, s), 8.31 (1H, s), 8.38 (1H, t). LC/MS t = 3.1 min, [MH+] 448 consistent with the molecular formula C2lH237 BrFN302.

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; GLAXO GROUP LIMITED; WO2005/75464; (2005); A1;,
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Application of 74586-53-1, A common heterocyclic compound, 74586-53-1, name is 3-Bromo-5-methylaniline, molecular formula is C7H8BrN, 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: 3-(trifluoromethyl) benzoic acid (511mg, 2.69mmol) was stirred in a solvent of 58 dimethyl formamide (10mL).The reaction solution was added with 59 HATU (1.12g, 2.96mmol), 72 DIPEA (890mul, 5.37mmol) and the appropriate substituted aromatic amine (500mg, 2.69mmol), followed by stirring for about 8h at room temperature. The reaction mixture was diluted with ethyl acetate and washed with a saturated aqueous sodium bicarbonate solution and saline. The organic layer thus obtained was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The resulting mixture was concentrated to give the crude product, which was purified by silica gel column chromatography (eluting with 0-5% EtOAc in 82 petroleum ether) to afford the 110 product as a white solid (815mg, 84%).

The synthetic route of 74586-53-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Qi; Dai, Yang; Ji, Yinchun; Shi, Huanyu; Guo, Zuhao; Chen, Danqi; Chen, Yuelei; Peng, Xia; Gao, Yinglei; Wang, Xin; Chen, Lin; Jiang, Yuchen; Geng, Meiyu; Shen, Jingkang; Ai, Jing; Xiong, Bing; European Journal of Medicinal Chemistry; vol. 163; (2019); p. 671 – 689;,
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1073-39-8, name is 3-Bromobicyclo[4.2.0]octa-1,3,5-triene, 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. Safety of 3-Bromobicyclo[4.2.0]octa-1,3,5-triene

To a mixture of 3-bromobicyclo[4.2.0]octa-1,3,5-triene (309.3 mg, 1.69 mmol, 1.20 equiv) in tetrahydrofuran (12 mL) was added n-BuLi (0.68 mL, 1.20 equiv, 2.5 M in hexane) dropwise at -78C. The solution was stirred for 30 min at -78C. To the resulting mixture was then added a solution of 5-bromo-2- ethylbenzaldehyde (300 mg, 1.41 mmol, 1.00 equiv) in tetrahydrofuran (3 mL) dropwise at -78C. The reaction mixture was stirred for 2 h at -78C. NH4CI/H20 was added and the mixture was extracted with ethyl acetate three times. The combined extracts were washed with brine and dried over Na2S04, then concentrated and purified by chromatography on silica gel (1 :5 EA/PE) to yield bicyclo[4.2.0]octa-1 (6),2,4-trien-3-yl(5-bromo-2-ethylphenyl)methanol as a yellow oil. MS (ES) m/z: 299.0, 301.0[M-OH]+.

The synthetic route of 1073-39-8 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;,
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Electric Literature of 4333-56-6, The chemical industry reduces the impact on the environment during synthesis 4333-56-6, name is Bromocyclopropane, I believe this compound will play a more active role in future production and life.

[000225j To a solution of Compound El (20 g, 96 mmol) in 1 -methyl-2-pyrrolidinone(300 mL) was added cesium carbonate (62.8 g, 193 mmol) and bromocyclopropane (24 mL,289 mmol). The mixture was stirred for 24 h while keeping the inner temperature between145 C and 155 C. After the reaction was cooled to ambient temperature, the dark solutionwas diluted with water (400 mL) and extracted with a mixture of ethyl acetate in petroleumether (15% v/v) (300 mL x 3). The combined organic phases were washed with brine (150mL x 4), dried over anhydrous sodium sulfate, filtered, and concentrated to afford the crude product. The crude product was purified with flash column chromatography on silica gel (petroleum ether) to furnish Compound E2. HPLC: Rt: 1.96 minute. ?H-NMR (CDC13, 400 MHz): 5 (ppm) 0.80-0.88 (m, 4H), 3.67-3.82 (m, 1H), 7.15 (d, J 8.8 Hz, 1H), 7.32 (dd, J 8.8, 2.4 Hz, 1H), 7.47 (d, J 2.4 Hz, 1H).

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, Bromocyclopropane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BIOMARIN PHARMACEUTICAL INC.; WANG, Bing; WO2015/65937; (2015); A1;,
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Synthetic Route of 7745-91-7, These common heterocyclic compound, 7745-91-7, name is 3-Bromo-4-methylaniline, 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: To a well stirred solution of compound 6a or 6b (0.2 g, 1 Eq.) in absolute ethanol (10 mL), the appropriately substituted anilines(1.1 Eq) was added and the reaction mixture was refluxed for 2-3 h until TLC showed full consumption of starting materials. The excess of solvent was evaporated under reduced pressure to yield the crude solids, which were further purified by recrystallization with methanol to afford the desired title compounds (7-43).

The synthetic route of 7745-91-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Cherukupalli, Srinivasulu; Chandrasekaran, Balakumar; Kry?tof, Vladimir; Aleti, Rajeshwar Reddy; Sayyad, Nisar; Merugu, Srinivas Reddy; Kushwaha, Narva Deshwar; Karpoormath, Rajshekhar; Bioorganic Chemistry; vol. 79; (2018); p. 46 – 59;,
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74586-53-1, name is 3-Bromo-5-methylaniline, 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. Application In Synthesis of 3-Bromo-5-methylaniline

Intermediate 5 N-(3-Bromophenyl)cyclohexanecarboxamide [00398] Cyclohexanecarbonyl chloride (61.4 g, 419 mmol) was added to a solution of 3- bromoaniline (60 g, 349 mmol), DMAP (4.26 g, 34.9 mmol), TEA (70.6 g, 698 mmol) in DCM (400 mL) at 0 C. The mixture was slowly warmed to 15 C and stirred for 14 h. Water (200 mL) was added, and the mixture was extracted with DCM (3 x300 mL). The combined organic phases were washed with brine (2×300 mL), dried over anhydrous Na2S04, filtered and concentrated. The residue was purified by recrystallization from MTBE (200 mL) to give N-(3- bromophenyl)cyclohexanecarboxamide (90 g, 85%) as a red brown solid. MS: 282.1 [M+H]+. The Intermediates below were synthesized from the appropriate amines following the procedure described for Intermediate 5. Note: DMAP was not used for the above Intermediates; reaction time: 2-16 h. *Acetonitrile was used as a solvent instead of DCM.

The synthetic route of 74586-53-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; METACRINE, INC.; SMITH, Nicholas D.; GOVEK, Steven P.; NAGASAWA, Johnny Y.; (228 pag.)WO2017/49172; (2017); A1;,
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Application of 583-70-0,Some common heterocyclic compound, 583-70-0, name is 2,4-Dimethylbromobenzene, 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.

Add 2,4-dimethylbromobenzene to a 500 mL three-necked flask equipped with magnetic stirring at room temperature.2,4-Dimethylaniline, Pd2(dba)3, tri-tert-butylphosphine, sodium t-butoxide, toluene.After the addition, the nitrogen gas was replaced 3 times, the stirring was started, and the oil bath was heated and heated to reflux for 5 hours.The TLC tracking reaction showed that the two starting materials were completely reacted (PE/EA = 20:1, product Rf = 0.8) and the reaction was stopped. The reaction solution was cooled to room temperature, stirred for 10 minutes with pure water, separated, and the aqueous phase was extracted with toluene, and the toluene phase was combined and saturated.Washed with brine, dried over anhydrous sodium sulfate, filtered and evaporatedDilute the crude product with as little petroleum ether as possible: dichloromethane = 10:1, and place the liquid on a silica gel column.Keep the polarity of the eluent unchanged with petroleum ether: dichloromethane = 10:1 until the product is rinsed.Dry under reduced pressure to give an off-white solid.Recrystallization from n-hexane gave 13 g of a white crystalline solid.HPLC 99.18%, yield 57%.

The synthetic route of 583-70-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Beijing Dingcai Technology Co., Ltd.; Gu’an Dingcai Technology Co., Ltd.; Gao Wenzheng; Ren Xueyan; (34 pag.)CN109665935; (2019); A;,
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