Tag: M.W=200-300

Application of 38762-41-3, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 38762-41-3 name is 4-Bromo-2-chloroaniline, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Synthesis of methyl 4?-amino-3 ?-chlorobiphenyl-4-carboxylate (65): A mixture of 4-bromo-2-chloroaniline (10 g, 48.5 mmol), 4-(methoxycarbonyl)phenylboronic acid (9.6 g,53.4 mmol), Pd(dppf)C12 (3.6 g, 4.85 mmol) and K2C03 (13.4 g, 97 mmol) in dioxane (100 mL) and water (10 mL) was degassed and heated at 100C for 2 h. After cooling down to room temperature, the reaction mixture was poured into water, extracted with EtOAc (100 mL X 3). The combined organic solvents were dried over anhydrous Na2504, concentrated under reduced pressure and purified by silica gel chromatography (10-50% EtOAc/petroleum ether) to give 11 g of methyl 4?-amino-3?-chlorobiphenyl-4-carboxylate 65 as black solid (86% yield). LCMS: m/z 262.1 [M+H], , tR= 1.98 min

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-2-chloroaniline, and friends who are interested can also refer to it.

Reference:
Patent; KARYOPHARM THERAPEUTICS INC.; BALOGLU, Erkan; SHACHAM, Sharon; SENAPEDIS, William; (153 pag.)WO2017/31213; (2017); A1;,
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These common heterocyclic compound, 110407-59-5, name is 2-Chloro-4-fluorobromobenzene, 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. Quality Control of 2-Chloro-4-fluorobromobenzene

Step 1 Ethyl 2′-chloro-4′-fluorobiphenyl-2-carboxylate To a reaction vessel were added 1-bromo-2-chloro-4-fluorobenzene (25 g), ethyl 2-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)benzoate (46 g), toluene (125 ml), water (125 ml) and tripotassium phosphate (50.5 g), and the reaction vessel was substituted with argon. To this mixture was added dichlorobis(triphenylphosphine)palladium(II) (1.67 g) and the mixture was stirred at an oil bath temperature 110 C. for 3 hr. The reaction vessel was removed from the oil bath, and water (125 ml) was added to the reaction mixture. The mixture was stirred at room temperature for 1 hr and filtered through celite. The filtrate was partitioned by pouring into a separating funnel. The aqueous layer was extracted with toluene, and combined with the organic layer. The organic layer was washed twice with water (125 ml), dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to give the title compound (41.8 g). The obtained solid was used for the next reaction without further purification. 1H-NMR (400 MHz, CDCl3) delta: 8.06-8.02 (1H, m), 7.60-7.54 (1H, m), 7.52-7.45 (1H, m), 7.27-7.16 (3H, m), 7.06-7.00 (1H, m), 4.18-4.09 (2H, m), 1.11-1.06 (3H, m).

The synthetic route of 2-Chloro-4-fluorobromobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JAPAN TOBACCO INC.; Motomura, Takahisa; US2014/296316; (2014); A1;,
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Adding a certain compound to certain chemical reactions, such as: 883499-24-9, name is 1-Bromo-2-chloro-3-fluorobenzene, belongs to chlorides-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 883499-24-9, Application In Synthesis of 1-Bromo-2-chloro-3-fluorobenzene

Under nitrogen environment,And at reflux temperature, 7-(diphenylamino)-9,9′-dimethyl-9H-fluoren-3-ol (100 g),1-bromo-2-chloro-3-fluorobenzene (58.3 g),The flask of potassium carbonate (91.5 g) and NMP (500 ml) was heated and stirred for 4 hours.After the reaction stopped, the reaction solution was cooled to room temperature, and water was added,The precipitate deposited was extracted by suction filtration. Use water in turn,After washing the obtained precipitate with methanol,Refined with silicone tubing (dissolved solution: toluene),Thus, 6-(3-bromo-2-chlorophenoxy)-9,9-dimethyl-N,N-diphenyl-9H-fluoren-2-amine (150 g) was obtained.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-2-chloro-3-fluorobenzene, and friends who are interested can also refer to it.

Reference:
Patent; KWANSEI GAKUIN EDUCATIONAL FOUNDATION; JNC CORPORATION; HATAKEYAMA, TAKUJI; MASUDA, KATSUYA; YAMAGA, YUKO; YANAI, MOTOKI; (214 pag.)TW2019/4977; (2019); A;,
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Application of 831-81-2, A common heterocyclic compound, 831-81-2, name is 4-Chlorodiphenylmethane, molecular formula is C13H11Cl, 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: In around-bottom flask, diarylmethanes (1.0 mmol), NBS (889.9 mg, 5.0 mmol) andwater (0 or 5.0 mmol) were dissolved in CHCl3 (4.0 mL). After refluxingfor 3 h in the air, the reaction mixture was quenched withNa2S2O3·5H2O, cooled to roomtemperature, washed with 5mL CH2Cl2, dried with MgSO4,and filtered to get clear organic solution. The solvent was removed reducedpressure by a rotary evaporator, and the resulting residue was subjected tocolumn chromatography on silica gel using co-solvent(ethyl acetate / petroleum ether, v/v) as eluent to give the correspondingdiaryllketones.

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:
Article; He, Chao; Zhang, Xiaohui; Huang, Ruofeng; Pan, Jing; Li, Jiaqiang; Ling, Xuege; Xiong, Yan; Zhu, Xiangming; Tetrahedron Letters; vol. 55; 32; (2014); p. 4458 – 4462;,
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Reference of 96558-78-0, The chemical industry reduces the impact on the environment during synthesis 96558-78-0, name is 3-Bromo-5-chlorophenylamine, I believe this compound will play a more active role in future production and life.

Preparation of starting material 3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (SM-17) This material was prepared from 3-bromo-5-chloroaniline following a similar procedure used for SM-9, step 3. The crude product was purified by flash chromatography (RediSep Cyano, Teledyne ISCO, 0-50% EtOAc in hexanes) to afford 3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (48%) as a pale orange solid: LCMS(m/z) 172.1 (MH+), tR=0.33 minute.

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-5-chlorophenylamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Costales, Abran Q.; Huang, Shenlin; Jin, Jeff (Xianming); Liu, Zuosheng; Pecchi, Sabina; Poon, Daniel; Tellew, John; US2011/52578; (2011); A1;,
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Related Products of 16793-91-2, 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. 16793-91-2, name is 2-Chlorophenethyl Bromide, This compound has unique chemical properties. The synthetic route is as follows.

Compound 28. 1 -(2-chlorophenethyl)-4-(2-methoxyphenethyl)piperidine A 250 mL round bottom flask was equipped with a magnetic stir bar, and then charged with 5 grams (0.0537 mol) of 4-picoline, 8.77 grams (0.0644 mol) of 2- methoxybenzaldehyde, and 50 ml of acetic anhydride. The reaction mass was heated to reflux and maintained at that temperature for 72 hours. The reaction mixture was then cooled to room temperature, and subjected to silica chromatography. Yield of (E)-4-(2- methoxystyryl)pyridine was 7.15 grams (63%). The 7.15 grams of (E)-4-(2- methoxystyryl)pyridine was then charged into a 500 mL hydrogenation flask, to which was added 100 mL of acetic acid as well as 50 mg of Pt02. The reaction mass was subjected to 45 psi of hydrogen gas, and allowed to react at room temperature for 16 hours. The reaction mixture was then filtered through a pad of celite, evaporated, basified with aqueous Na2C03 solution, and extracted with dichloromethane. The combined extraction solvents were removed under reduced pressure via rotovap. The residue was then subjected to silica chromatography, yielding 6.1 grams (82.1 % yield) of 4-(2-methoxyphenethyl)piperidine. A 100 mL round bottom flask equipped with a magnetic stir bar was then charged with 1.0 grams of 4-(2-methoxyphenethyl)piperidine (0.0046 mol), 1 .41 grams of 2- chlorophenethyllbromide (0.0064 mol), 1.87 grams of K2C03 (0.0135 mol), and 20 mL of DMF as solvent. The reaction mass was then heated to 70 C for 24 hours. The excess DMF was removed via reduced pressure, partitioned with water and dichloromethane, the organic layer separated; excess solvent removed under reduced pressure and the residue was subjected to silica chromatography. Yield of l-(2-chlorophenethyl)-4-(2- methoxyphenethyl)piperidine was 1.12 grams (68.0% yield). 1H NMR (300 MHz, CDC13) delta 1.40-1.62 (m, 7H), 2.41-2.75 (m, 10H), 3.84 (s, 3H), 6.92-7.73 (m, 8H) ppm.

The chemical industry reduces the impact on the environment during synthesis 2-Chlorophenethyl Bromide. I believe this compound will play a more active role in future production and life.

Reference:
Patent; UNIVERSITY OF KENTUCKY RESEARCH FOUNDATION; CROOKS, Peter, A.; DWOSKIN, Linda, P.; CULVER, John; NICKELL, Justin, R.; ZHENG, Guangrong; WO2014/144064; (2014); A2;,
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Application of 1298031-94-3, A common heterocyclic compound, 1298031-94-3, name is 8-Bromo-6-chloro-2-methylimidazo[1,2-b]pyridazine, molecular formula is C7H5BrClN3, 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.

8-Bromo-6-chloro-2-methylimidazo[l,2-b]pyridazine (1.0 g, 4.0 mmol) was combined with K2C03 (1.1 g, 8 mmol) and phenol (0.6 g, 6.0 mmol) in NMP (10 mL). The mixture was stirred at 60 C for 16 h. The mixture was partitioned between EtOAc and H20. The organic layer was washed with brine, dried over Na2S04, filtered and concentrated. The residue was chromatographed on silica gel, eluting with 0-30% EtOAc in petroleum ether to yield 6-chloro-2- methyl-8-phenoxyimidazo[l,2-b]pyridazine (560 mg, 53%). MS m/z 260.0, 262.0 [M+H]+.

The synthetic route of 1298031-94-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PTC THERAPEUTICS, INC.; WOLL, Matthew, G.; AMEDZO, Lukiana; BABU, Suresh; BARRAZA, Scott, J.; BHATTACHARYYA, Anuradha; KARP, Gary, Mitchell; MAZZOTTI, Anthony, R.; NARASIMHAN, Jana; PATEL, Jigar; TURPOFF, Anthony; XU, Zhenrong; (251 pag.)WO2018/226622; (2018); A1;,
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Application of 13526-66-4, These common heterocyclic compound, 13526-66-4, name is 3-Bromo-6-chloroimidazo[1,2-b]pyridazine, 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.

13.9 g (59.8 mmol) 3-bromo-6-chloro-imidazo[1 ,2-6]pyridazine were suspended in 508 mL 1 ,4-dioxane. 10, 1 g (62.8 mmol) 2-benzofuranylboronic acid, 2.76 g (2.29 mmol) tetrakis(triphenylphosphino)palladium-(0) and 19.0 g (179 mmol) sodium carbonate were added. The obtained mixture was heated to 100 C for 24 h.400 mL of a saturated aqueous ammonium chloride solution were added. The obtained mixture was extracted with ethyl acetate. The combined organic layers were washed with brine and dried over magnesium sulfate. After evaporation of the solvent, the obtained solid material was digested in 40 mL of a mixture of dichioromethane and methanol (8:2), filtered off and dried in vacuo to yield 5.42 g (44%) of the title compound as solid material. 1H-NMR (300 MHz, DM50-d6): delta [ppm]= 7.23 – 7.40 (m, 2H), 7.51 (d, 1 H), 7.59 – 7.67 (m, 2H), 7.77 (d, 1 H), 8.33 – 8.40 (m, 2H).LCM5 (Method 1 ): Rt = 1 .35 min; MS (ESIpos) m/z = 270 [M+H]

Statistics shows that 3-Bromo-6-chloroimidazo[1,2-b]pyridazine is playing an increasingly important role. we look forward to future research findings about 13526-66-4.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; KNUT, Eis; PUeHLER, Florian; ZORN, Ludwig; SCHOLZ, Arne; LIENAU, Philip; GNOTH, Mark; BOeMER, Ulf; GUeNTHER, Judith; FANGHAeNEL, Joerg; KORR, Daniel; WO2012/163942; (2012); A1;,
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Application of 50594-82-6,Some common heterocyclic compound, 50594-82-6, name is 3,4,5-Trichlorobenzotrifluoride, molecular formula is C7H2Cl3F3, 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.

PRODUCTION EXAMPLE 3 (Production of Compound No. (3)) After 44 mg (1.1 mmol) of 60% sodium hydride was added to a solution of 0.14 g (1 mmol) of 5-(1-methylcyclopropyl)-1,3,4-oxadiazolin-2-one in 5 ml of N,N-dimethylformamide at room temperature, the mixture was stirred at the same temperature for 15 minutes. To the mixture was added 0.25 g (1 mmol) of 3,4,5-trichlorobenzotrifluoride followed by heating a 80 C. for 6 hours. After cooling, the mixture was poured into water and extracted with ethyl acetate. After drying over magnesium sulfate, the extract was concentrated under reduced pressure to give the crude product. The crude product was subjected to silica gel column chromatography to give 35 mg of 5-(1-methylcyclopropyl)-3-(2,6-dichloro-4-trifluoromethylphenyl)-1,3,4-oxadiazoline-2-one. m.p. 107.1 C.

The synthetic route of 50594-82-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sumitomo Chemical Company, Limited; US5124341; (1992); A;,
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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. 766545-20-4, name is 2-Chloro-5,6,7,8-tetrahydro-1,6-naphthyridine hydrochloride, A new synthetic method of this compound is introduced below., Product Details of 766545-20-4

Preparation 26 2-Amino-1-(7w8-dihydro-5H-r1, 61naphthvridin-6-yl)-ethanone; Step A A solution of 90 mg of 2-chloro-5, 6,7, 8-tetrahydro- [1, 6] naphthyridine hydrochloride (U. S. Pat. No. 6,169, 093), 0.134 g of N-carbobenzyloxyglycine, 0.130 g of triethylamine, and 0.087 g of 1-hydroxy-7-azabenzotriazole in DMF (2.7 mL) at 0 C was stirred as 0.123 g (0.640 mmol) of EDC was added. After two h, the reaction mixture was poured into 4% magnesium sulfate solution, and the resulting solution was extracted with EtOAc and then methylene chloride. The organic extracts were dried over sodium sulfate, filtered, and concentrated to give an oil that solidified upon standing. Trituration with MeOH and collection of the solids provided the desired amide intermediate.

The synthetic route of 766545-20-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2005/35532; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics