Tag: M.W=100-200

Synthetic Route of 58534-95-5,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.

Step 4ATo a solution of 3-bromo-2-fluoroaniline 4a (228 mg) in DCM (5 ml) were added 2,6-difluorobenzene-1-sulfonyl chloride (280 mg), pyridine (120 mg) and DMAP (3 mg). The reaction mixture was stirred overnight at room temperature. iN HC1 was added toquench the reaction, and then the organic phase was washed with brine, dried over Na2504, filtered and concentrated. The residue was purified by chromatography to give desired product 4b (200 mg 47% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Bromo-2-fluoroaniline, its application will become more common.

Reference:
Patent; ETERNITY BIOSCIENCE INC.; LIU, Dong; ZHANG, Minsheng; WO2014/182873; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 1003-99-2,Some common heterocyclic compound, 1003-99-2, name is 2-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.

Example la. 3-Fluorophenanthridin-6-ol1 aA mixture of 2-(ethoxycarbonyl)phenylboronic acid (7.0 g, 39 mmol), 2-bromo-5- fluoroaniline (7.4 g, 39 mmol), dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (S- Phos, 0.32 g, 0.78 mmol), sodium acetate (4.1 g, 39 mmol), and palladium acetate (0.087 g, 0.39 mmol) in 18 ml. of ethanol was heated with stirring at 80° C for 18 h. Additional 2- (ethoxycarbonyl)phenylboronic acid (2.0 g), S-Phos (0.095 g), palladium acetate (0.020 g), and sodium carbonate (1.2 g) was added and the mixture was stirred for 18 h. The solvent was removed by evaporation under reduced pressure, and the resulting solid was isolated by vacuum filtration, washing the remaining solid with water and then hexane. The remaining solid and dried in vacuo @ 50° C to provide the title compound (4.39 g, 53percent yield) which was used without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-5-fluoroaniline, its application will become more common.

Reference:
Patent; ENANTA PHARMACEUTICALS, INC.; ABBOTT LABORATORIES; MCDANIEL, Keith, F.; CHEN, Hui-ju; SHANLEY, Jason, P.; GRAMPOVNIK, David, J.; GREEN, Brian; MIDDLETON, Timothy; HOPKINS, Todd; OR, Yat, Sun; WO2012/92411; (2012); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 1647-26-3, A common heterocyclic compound, 1647-26-3, name is 1-Bromo-2-cyclohexylethane, molecular formula is C8H15Br, 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: The compounds were prepared according to the procedure previouslydescribed.19,30 To a refluxing solution of thiazolidine-2,4-dione (43 mmol) in ethanol (25 mL) was added a hot solutionof potassium hydroxide (45 mmol) in ethanol (25 mL). After additionalrefluxing for 30 min, the mixture was cooled to room temperatureand the precipitate was filtered and washed with coldethanol. The obtained potassium 2,4-dioxothiazolidin-3-ide (2)(5 mmol) was refluxed with alkyl halides (5.5 mmol) in DMF(15 mL) for 3-4 h. After cooling to room temperature and additionof water (50 mL), the crude product was extracted 3 times withethyl acetate, washed with brine, and purified by flash chromatography(cyclohexane/ethyl acetate).

The synthetic route of 1647-26-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bastos Lima, Allan; Behnam, Mira A.M.; El Sherif, Yasmin; Nitsche, Christoph; Vechi, Sergio M.; Klein, Christian D.; Bioorganic and Medicinal Chemistry; vol. 23; 17; (2015); p. 5748 – 5755;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 10269-01-9, name is (3-Bromophenyl)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 10269-01-9, Safety of (3-Bromophenyl)methanamine

General procedure: N,N’-di(2-fluorophenyl)-4-methoxyl-isophthalamide(1a): Equipped a stirrer in a three-necked flask (100 ml), to a mixture of 2-fluoroaniline (1.11 g, 10.0 mmol),anhydrous tetrahydrofuran (15 ml) and dry pyridine (1 ml), dropwise added 4-methoxyl-isophthaloyl dichloride (1.17 g, 5.0 mmol) which had been dissolved in dry tetrahydrofuran (10 ml). After the mixture reaction at room temperature for 8 h under continuous stirring, the excess tetrahydrofuran was distilled off in vacuum. The residue was recrystallized by acetone. Its melting point is 204-206 C, and yield is 67%. The other compounds 1b-1j, 2a-2k, 3a-3l and 4a-4h were prepared in the same manner.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (3-Bromophenyl)methanamine, and friends who are interested can also refer to it.

Reference:
Article; Liu, Xiu Jie; Shi, Xin Xin; Zhong, Yong Liang; Liu, Ning; Liu, Kai; Bioorganic and medicinal chemistry letters; vol. 22; 21; (2012); p. 6591 – 6595,5;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 2695-47-8, name is 6-Bromo-1-hexene, 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. HPLC of Formula: C6H11Br

General procedure: A 70 ml oven dried autoclave containing a stirrer bar wascharged the AgI (0.5 mg, 0.002 mmol) and Cs2CO3 (978 mg, 3.0mmol). The autoclave was purged three time with CO2 and theterminal alkynes 1 (2.0 mmol), bromides 2 (3.0 mmol), and dryDMF (20 ml) were then added sequentially via a syringe. Theautoclave was then sealed and pressurized to the appropriatepressure with CO2. The reaction mixture was then stirred at 60C for 24 h and the autoclave was cooled to room temperatureand the remaining CO2 slowly vented from the system. Thereaction mixture was diluted with water (30 ml) and extractedwith ethyl acetate (30 ml × 3). The combined organic layerswere washed with water and brine, dried over Na2SO4, andfiltered. The solvent was removed under vacuum. The productwas isolated by column chromatography on silica gel.

The synthetic route of 6-Bromo-1-hexene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Linlin; Zhang, Wenzhen; Shi, Linglong; Ren, Xiang; Lue, Xiaobing; Cuihua Xuebao/Chinese Journal of Catalysis; vol. 34; 6; (2013); p. 1179 – 1186;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 3814-30-0, The chemical industry reduces the impact on the environment during synthesis 3814-30-0, name is (Bromomethyl)cyclopentane, I believe this compound will play a more active role in future production and life.

Example 4 7-(Cyclopentylmethyl)-3-propyl-[1,2,4]triazolo[4,3-a]pyrazin-8(7H)-one: To a solution of 3-propyl-[1 ,2,4]thazolo[4,3-a]pyrazin-8(7H)-one (200 mg, 1 .1 mmol) and (bromomethyl)cyclopentane (283 mg, 1 .35 mmol) in DMF (2 ml_) was added K2CO3 (310 mg, 2.2 mmol). The reaction was stirred at 60 C for 4 hours and then cooled to RT. The mixture was diluted with DCM (20 ml_) and washed with water (2×5 ml_). The organic layer was dried over Na2SO4 and evaporated. The crude product was washed with MeOH (2 ml_) to give 7-(cyclopentylmethyl)-3-propyl- [1 ,2,4]triazolo[4,3-a]pyrazin-8(7H)-one 120 mg (41 %) . 1H NMR (CDCI3, 400 MHz TMS): delta 6.91 (d, J=5.6 Hz, 1 H), 6.66 (d, J=5.6 Hz, 1 H), 3.89 (d, J=8.0 Hz, 2H), 2.94 (t, J=7.6 Hz, 2H), 2.37-2.31 (m, 1 H), 1 .92-1 .86 (m, 2H), 1 .73-1 .68 (m, 4H), 1 .63-1 .56 (m, 2H), 1 .32-1 .27 (m, 2H), 1 .04 (t, J=7.4 Hz, 3H). LCMS (MH+): m/z = 261 .1 , tR (minutes, Method 3) = 2.41

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, (Bromomethyl)cyclopentane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; H. LUNDBECK A/S; KEHLER, Jan; RASMUSSEN, Lars, Kyhn; JESSING, Mikkel; (126 pag.)WO2016/55618; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 2550-36-9, 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. 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.

To a solution of 3-(tetrahydro-2H-pyran-4-yl)imidazo[1 ,5-a]pyrazin-8(7H)-one (300 mg, 1 .37 mmol) in anhydrous DMF (5 mL) was added K2003 (379 mg, 2.74mmol) and (bromomethyl)cyclohexane (364 mg, 2.06 mmol). The reaction mixture was stirred at 60C for 16 hours. The mixture was filtered and the filtrate was purified by preparative LC-MS to yield 7-(cyclohexylmethyl)-3-(tetrahydro-2H-pyran-4-yl )imidazo[1 ,5-a]pyrazin-8(7H)-one 240 mg (55%).1H NMR (DMSO-d6, 400 Mhz): 7.62 (s, 1H), 7.47 (d, J= 6.0 Hz, 1H), 6.84 (d, J= 6.2 Hz,1H), 3.91-3.88 (m, 2H), 3.60 (d, J= 7.2 Hz, 2H), 3.48-3.42 (m, 2H), 3.30-3.29 (m, 1H), 1.78-1.52 (m, 1OH), 1.10-1.06 (m, 3H), 0.93-0.91 (m, 2H).LC-MS: (mlz) 316.2 (MH) tR (minutes, method 3) = 2.44 minutes.

The synthetic route of (Bromomethyl)cyclohexane has been constantly updated, and we look forward to future research findings.

Reference:
Patent; H. LUNDBECK A/S; KEHLER, Jan; RASMUSSEN, Lars, Kyhn; LANGGARD, Morten; JESSING, Mikkel; VITAL, Paulo, Jorge, Vieira; JUHL, Karsten; (159 pag.)WO2016/174188; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 656-64-4,Some common heterocyclic compound, 656-64-4, name is 3-Bromo-4-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.

A solution of 3-bromo-4-fluoroaniline (1.9 g, 10.00 mmol) and 5- (methoxymethylene)-2,2-dimethyl- 1,3 -dioxane-4,6-dione (2.234 g, 12.00 mmol) in dioxane (5 mL) was heated to 120 C for 20 minutes. The reaction mixture is then cooled to room temperature and diluted with 50 ml of dietheyl ether. The solid was filtered and dried to give 5 -(((3 -bromo-4-fluorophenyl)amino)methylene)-2,2-dimethyl- 1,3 -dioxane4,6-dione (2.77 g, 8.0 mmol, 80%). ?HNMR(400 MHz, DMSO-d6) oe 11.23 (br d, J=14.4 Hz, 1H), 8.53 (d, J=14.5 Hz, 1H), 8.06 (dd, J=6.0, 2.8 Hz, 1H), 7.69 – 7.61 (m, 1H), 7.44 (t, J=8.7 Hz, 1H), 1.73 – 1.63 (m, 6H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Bromo-4-fluoroaniline, its application will become more common.

Reference:
Patent; INNATE TUMOR IMMUNITY, INC.; O’MALLEY, Daniel; GAVAI, Ashvinikumar V.; GILL, Patrice; TARBY, Christine M.; WATTERSON, Scott Hunter; GONG, Hua; WILLIAMS, David K.; GHOSH, Shomir; ROUSH, William R.; (307 pag.)WO2019/14402; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 766-81-4,Some common heterocyclic compound, 766-81-4, name is 3-Bromophenylacetylene, molecular formula is C8H5Br, 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.

Under nitrogen protection, the product of step 1 and 2.5 equivalents of m-bromophenylacetylene and 0.05 equivalent of cuprous iodide in a solution of diisopropylamine and dichloromethane (volume ratio 1:10) was reacted under nitrogen atmosphere at room temperature for 24 h . The product was isolated on a silica gel column and the yield was 75-80%.

The synthetic route of 766-81-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dalian University of Technology; Ni, Jun; Gai, Xuqiao; Kang, Jiajia; Xu, Liang; (7 pag.)CN105732721; (2016); A;,
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. 399-94-0, name is 1-Bromo-2,5-difluorobenzene, A new synthetic method of this compound is introduced below., COA of Formula: C6H3BrF2

Under N2 protection, 2,5-difluorobromobenzene (15.05 g, 78 mmol) was dissolved in dry toluene (50 ml), cooledto -10C or lower in an ice salt bath, and a solution of isopropyl magnesium chloride/lithium chloride in tetrahydrofuran(66 ml, 1.3 mol/l) was added dropwise, followed by stirring at about -10C for 1 hour. 1D (10 g, 39 mmol) was dissolvedin dry tetrahydrofuran (100 ml), and added dropwise to the reaction solution while the temperature was maintained at-10C. When the addition was complete, the reaction was allowed to proceed at room temperature for 4 hours. Thetemperature was lowered to about -10C, and a saturated ammonium chloride solution (40 ml) was added dropwise,followed by stirring for 10 min. The pH was adjusted to 5 to 6 with a 3 mol/l hydrochloric acid solution, to allow settlingand partitioning. The aqueous phase was extracted with methyl t-butyl ether (50 ml32). The organic phases werecombined, washed with a saturated sodium chloride solution (30 ml32), dried by addition of anhydrous sodium sulfatethereto, filtered, concentrated, and separated by column chromatography (petroleum ether/ethyl acetate (v/v) = 50:1 to8:1), to obtain a light yellow solid 1E (10.1 g, yield 83.5%).MS m/z (ESI): 210.1 [M-99].

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; Sichuan Haisco Pharmaceutical Co., Ltd.; ZHANG, Chen; WANG, Jianmin; LI, Caihu; WEI, Yonggang; (64 pag.)EP3159344; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary