Tag: M.W=200-300

Reference of 873-38-1, 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. 873-38-1, name is 2-Bromo-4-chloroaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

In a 20 mL microwave vial was added 2-bromo-4-chloroaniline (3 g, 14.53 mmol), 4,4,5, 5-tetramethyl-2-(tetramethyl-l,3,2-dioxaborolan-2-yl)-l,3,2-dioxaborolane (5.53 g, 21.80 mmol), KOAc (3.66 g, 37.3 mmol), Pd(dppf)Cl2-CH2Cl2adduct (0.32 g, 0.44 mmol) and DMSO (9 mL). The resulting suspension was purged with N2, capped and heated at 80 C for 22 h. The reaction was cooled to rt. Water was added to dissolve the salts, then the reaction was filtered. The remaining solid was suspended in DCM and the insoluble solid was filtered. The filtrate was concentrated and then purified by normal phasechromatography to give 4-chloro-2-(tetramethyl-l ,3,2-dioxaborolan- 2-yl)aniline (3.15 g, 86 % yield) as a white solid. MS (ESI) m/z: 172.3 (M-CeHio+H)+. NMR (400MHz, CDCh) delta 7.54 (d, J=2.6 Hz, IH), 7.13 (dd, J=8.8, 2.6 Hz, IH), 6.52 (d, J=8.6 Hz, IH), 4.72 (br. s., 2H), 1.34 (s, 12H).

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-Bromo-4-chloroaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; ZHU, Yeheng; DILGER, Andrew K.; EWING, William R.; ORWAT, Michael J.; PINTO, Donald J.P.; (156 pag.)WO2017/19821; (2017); A1;,
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Related Products of 50594-82-6, 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. 50594-82-6, name is 3,4,5-Trichlorobenzotrifluoride belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 3; Preparation method of 3,4,5-trifluorobenzotrifluoride; 860 g of dry sulpholane and 524 g of dry KF were initially charged with exclusion of moisture in an autoclave, and 500 g of 3,4,5-trichlorobenzotrifluoride, 5 g of nitrobenzene and 25 g of CNC catalyst were added. The vessel was sealed and the mixture subsequently heated to 200 C. for 5 h and then to 220 C. for a further 12 h. During the reaction, a maximum total pressure of 9 bar arose. The mixture was then cooled to 20 C. and decompressed into a cooled receiver. The product was distilled off at standard pressure. After redistillation of the crude product, 300 g of 3,4,5-trifluorobenzotrifluoride (75% of theory) were obtained as a colourless liquid.

The synthetic route of 3,4,5-Trichlorobenzotrifluoride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pleschke, Axel; Marhold, Albrecht; US2006/9643; (2006); A1;,
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Synthetic Route of 468075-00-5, The chemical industry reduces the impact on the environment during synthesis 468075-00-5, name is 2-Bromo-1-chloro-4-(trifluoromethoxy)benzene, I believe this compound will play a more active role in future production and life.

(Description 25; [L.] [OG,] 3.6mmol) and tri-n-butylvinyl tin (1.21g, 3. [8MMOL)] were dissolved in toluene (20mL) and the solution was degassed for 45 minutes with nitrogen. Tetrakis (triphenylphosphine) palladium [(0)] (lOOmg) was then added and the solution heated at reflux for 2 hours. Once cooled, the solution was concentrated and the residue was purified by silica chromatography to give the title compound [(274MG,] [1.] [2MMOL).] [ON] (360 MHz, [CDCL3)] : 7.40-7. 36 (2H, m), 7.09-7. 01 (2H, m), 5.75 [(1H,] d, J 17.5Hz), 5.47 [(1H,] d, J [10.] 9Hz).

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-Bromo-1-chloro-4-(trifluoromethoxy)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME LIMITED; WO2004/31190; (2004); A1;,
Chloride – Wikipedia,
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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 933190-51-3 as follows. Recommanded Product: 8-Bromo-6-chloroimidazo[1,2-b]pyridazine

Step 3a. Preparation of (6-Chloro-imidazo[1,2-b]pyridazin-8-yl)-[5-(4-methyl-piperazin-1-ylmethyl)-pyridin-2-yl]-amine A mixture of 8-bromo-6-chloroimidazo[1,2-b]pyridazine (214 mg, 921 mumol, Eq: 0.95) and 5-((4-methylpiperazin-1-yl)methyl)pyridin-2-amine (200 mg, 970 mumol, Eq: 1.00) in DMF (10.0 ml) was cooled to 0 C. To this was added sodium hydride (60% in mineral oil, 124 mg, 3.1 mmol, Eq: 3.2). The reaction was allowed to stir at 0 C. for 10 min and then allowed to warm to room temperature and stirred for 72 h. The reaction was quenched with saturated NaHCO3 (aq) and then diluted with water and EtOAc. The organic layer was separated and the aqueous phase was washed with EtOAc. The organic layers were combined, dried over MgSO4 and concentrated in vacuo. The residue was dissolved in Et2O. The organic layer was washed with water and dried over MgSO4. The drying agent was removed by filtration. The resulting solution was concentrated in vacuo to give (6-chloro-imidazo[1,2-b]pyridazin-8-yl)-[5-(4-methyl-piperazin-1-ylmethyl)-pyridin-2-yl]-amine (170 mg, 49%) as a solid. LC/MS-ESI observed [M+H]+ 358.

According to the analysis of related databases, 933190-51-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hoffmann-La Roche Inc.; Brotherton-Pleiss, Christine E.; Lopez-Tapia, Francisco Javier; Lou, Yan; US2013/150360; (2013); A1;,
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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. 1996-29-8, name is 1-Bromo-4-chloro-2-fluorobenzene, This compound has unique chemical properties. The synthetic route is as follows., name: 1-Bromo-4-chloro-2-fluorobenzene

To a stirred and cooled (-78 C) solution of 1-bromo-4-chloro-2-fluorobenzene (1.0 mL, 8.012 mmol) in diethyl ether (10 mL) was added n-BuLi (1.6 M in ether, 5 mL) and stirred for 30 mm. A solution of 1,3-dichloroacetone (1.01 g, 8.012 mmol) in diethyl ether (10 mL) was added to the reaction mixture at -78 C and stirred at -78C to 0 C for lh. To that mixture was added a solution of ferric chloride (26 mg,0.163 mmol) in diethyl ether (5 mL) followed by ethyl magnesium bromide (13.3 mL,40.059 mmol) at 0 C and gradually warmed to RT. The reaction mixture was stirredat RT for 18 h. The reaction mixture was quenched with saturated ammoniumchloride solution (50 mL). The aqueous mixture was extracted with ethyl acetate (2 x100 mL). The combined organic layers were washed with water (100 mL) and driedover anhydrous sodium sulfate. The solution was filtered, concentrated under reduced pressure and the residue thus obtained was purified by silica gel column chromatography to yield 425 mg of the product as a semi-solid. ?H NMR (300 MHz, DMSO-d6) oe 0.96 (d, J = 10.2 Hz, 4H), 6.02 (s, 1H), 7.24 (d, J = 8.7 Hz, 1H), 7.33 (dJ = 9.3 Hz, 1H), 7.51 (t, J = 8.7 Hz, 1H).

According to the analysis of related databases, 1996-29-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLENMARK PHARMACEUTICALS S.A.; CHAUDHARI, Sachin Sundarlal; THOMAS, Abraham; KADAM, Ashok Bhausaheb; DHONE, Sachin Vasantrao; ADIK, Bharat Gangadhar; KHAIRATKAR-JOSHI, Neelima; SHAH, Daisy Manish; BAJPAI, Malini; WO2015/159233; (2015); A1;,
Chloride – Wikipedia,
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Reference of 2770-11-8, 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. 2770-11-8 name is 2-(4-Chlorophenoxy)aniline, 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.

4-[2-(4-Chlorophenoxy)phenylcarbamoyI]piperidine-l-carboxylic acid fer/-butyl ester (AMR01031) C23H27ClN2O4, MW 430,92A solution of piperidine-l,4-dicarboxylic acid mono-tert-butyl ester (AMRO 1030, 417 mg, 1.82 mmol) in dry DCM (8 mL) was stirred under nitrogen, and 4- dimethylaminopyridine (DMPA, 40 mg, 0.327 mmol), (l-(3-dimemylaminopropyl)-3- ethylcarbodiimide hydrochloride (EDC, 1.05 g, 5.46 mmol) and triethylamine (0.25 mL) were added. The resulting mixture was stirred for 30 min under nitrogen and 2-(4-chloro- phenoxy)-phenylamine (AMR01029, 400 mg, 1.82 mmol) in dry DCM (4 mL) was added. After stirring at room temperature for 24 h, the mixture was diluted with DCM, washed EPO with HCl IM (3 x 25 mL), water, saturated NaHCO3 (2 x 25 mL) and brine. The organic layer was dried (MgSO4), filtered and evaporated. Flash chromatography on silica gel of the crude product using hexane/EtOAc 8:2 as eluent gave starting material (104 mg). Further elution using hexane/EtOAc 7:3 gave 4-[2-(4-chlorophenoxy)- phenylcarbamoyl]piperidine-l-carboxylic acid tert-butyl ester (430 mg, 55%) as a white solid, mp 97-99 0C. Rf: 0.22 (hexane/EtOAc 7:3) LC/MS (APCI) tr = 3.83 min, m/z 431.23 (33), 429.21 (M’-H,100). 1H NMR (270 MHz, CDCl3) ¡ê 1.44 (9H5 s, 3CH3), 1.68 (2H, m, CH2), 1.83 (2H, m, CH2), 2.36 (IH, tt, J= 11.4, 3.7 Hz), 2.75 (4 H, br t, 2CH2), 4.11 (4H, m, 2CH2), 6.81 (IH, dd, J= 8.2, 1.5 Hz, ArH), 6.93 (2H, AA’BB’, ArH), 7.01 (IH, td, ArH), 7.12 (IH, td, ArH), 7.31 (2H, AA’BB’, ArH), 7.68 (IH, br s, NH) and 8.40 (IH, dd, J= 6.9, 1.5 Hz, ArH).

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

Reference:
Patent; STERIX LIMITED; WO2007/3934; (2007); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 13918-92-8, 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 13918-92-8 as follows.

General procedure: To a solution of 5-bromo-2-methoxypyridin-3-amine (1) (2.01 g,10 mmol) in pyridine (50 ml) at 0 C, 4-fluorophenylsulfonylchloride (2.14 g, 11 mmol) was added. Then the mixture was stirredat room temperature for 24 h. Pyridine was removed underreduced pressure and adding water (100 ml), extracted with ethylacetate (3 100 ml), the organic layer was washed with water(50 ml), dried with Na2SO4 and evaporated to give compound 2a asa white solid (3.22 g, 89.4% yield).

According to the analysis of related databases, 13918-92-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Fan, Yan-Hua; Li, Wei; Liu, Dan-Dan; Bai, Meng-Xuan; Song, Hong-Rui; Xu, Yong-Nan; Lee, SangKook; Zhou, Zhi-Peng; Wang, Jian; Ding, Huai-Wei; European Journal of Medicinal Chemistry; vol. 139; (2017); p. 95 – 106;,
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Application of 174913-12-3, A common heterocyclic compound, 174913-12-3, name is 1-Bromo-3-chloro-5-methoxybenzene, molecular formula is C7H6BrClO, 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.

Bromo-3-chloro-5-methoxybenzene (10 mmol, 2.2 g)Diphenylamine (20 mmol, 3.34 g) was added to a 100 mL three-necked flask,A cuprous iodide (2 mmol, 0.4 g) was added under nitrogen,Potassium carbonate (20 mmol, 1.4 g),O-phenanthroline (2 mmol, 0.4 g),50 mL of DMF,Reaction was carried out at 155 C for 3 days;The resulting reaction product is subjected to extraction,The extracted organic phase was evaporated to dryness with ethanol,Then recrystallized from ethyl acetate and petroleum ether,To obtain 1.83 g of intermediate A-1,

The synthetic route of 174913-12-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jilin Aolai De Optoelectronic Materials Co., Ltd.; Gao, Chunji; Cui, Dunzhu; Sun, Yi; Zhang, Chengcheng; (52 pag.)CN104892434; (2017); B;,
Chloride – Wikipedia,
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Synthetic Route of 210532-25-5, 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. 210532-25-5, name is 3,5-Difluorobenzene-1-sulfonyl chloride belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 2; N-r5-( 4-Amino-7 -isopropvl-7 H-pvrrolor2 .3-dl pvrim idine-5-carbonvl)-pvrid in-3-vll-3,5- difluoro-benzenesulfonamide; 3,5-Difluoro-benzenesulfonyl chloride (19.7 mg, 0.093 mmol) was added to a solution of (4-Amino-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-(5-amino-pyridin-3-yl)-methanone (25 mg, 0.084 mmol) in pyridine (0.7 mL). The resulting solution was heated to 40 C for 16 h. The reaction mixture was concentrated in vacuo and the residue dissolved in DMSO (2 mL) and purified using reverse phase preparative HPLC to furnish the title compound as a white solid. MS: 473.2 (MH+) ; HPLC Rf: 4.91 min. (HPLC method 4).

The synthetic route of 3,5-Difluorobenzene-1-sulfonyl chloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2005/116035; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 873-38-1, These common heterocyclic compound, 873-38-1, name is 2-Bromo-4-chloroaniline, 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.

To a well-stirred mixture consisting of 2-bromo-4-chloroaniline (5.0 g, 24 mmol) in tetrahydrofuran (180 ML), diethyl-3-pyridyl borane (4.07 g, 28 MMOL), and bis (TRIPHENYLPHOSOPHINE) PALLADIUM (II) chloride (2.53 g, 3.6 mmol), a solution of sodium carbonate (12.72 g, 120 MMOL) in water (60 ML) was added. The reaction was then heated at 75C for 18 hours. The layers of the biphasic mixture were separated, and the aqueous phase was extracted with an equal volume of ethyl acetate. The combined original reaction organic phase and ethyl acetate extract were dried and concentrated in vacuo to afford an oil (9.4 g). Flash chromatography of the entire sample (silica gel ; initial elution with ethyl acetate/hexanes = 8: 2 in volume followed by elution with pure hexane) afforded the title compound as a colorless oil (3.64 g, 74% yield). TLC Rf (silica gel plates ; elution with ethyl acetate, UV detection): 0.46.

The synthetic route of 873-38-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2004/43929; (2004); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics