Tag: M.W=200-300

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. 954235-83-7, name is 1-Bromo-2-(difluoromethoxy)-4-fluorobenzene, A new synthetic method of this compound is introduced below., Recommanded Product: 1-Bromo-2-(difluoromethoxy)-4-fluorobenzene

A mixture of l -bromo-2-(difluoromethoxy)-4-fluorobenzene (intennediate 176a, 75 mg), (6-(2- (4-(ethylsulfonyl)phenyl)acetamido)-2-methylpyridin-3-yl)boronic acid (intermediate 178a, 310 mg), PdCl2(dppf)-CH2Cl2 adduct (20.33 mg) and Na2COj (39.6 mg) in acetonitrile (2.4 mL)/water (0.8 mL) was sealed in a vessel and heated in the microwave at 100C for 45 mins. The mixture was filtered through celite and silica gel. The filtrate was concentrated under reduced pressure and the residue was purified by MDAP to afford N-(5-(2-(difIuoromethoxy)-4-fluorophenyl)-6-methylpyridin-2-yl)-2-(4- (ethyIsulfonyl)phenyi)acetarnide, trifluoroacetic acid salt (16 mg) as a white solid. ?-NMR (400 MHz, DMSO-i¾) delta ppm 1.10 (t, J= 7.2 Hz, 3H), 2.21 (s, 3H), 3.27 (q, J= 7.2 Hz, 2H), 3.89 (s, 2H), 7.22 (t, J= 72 Hz, 1H), 7.24 (m, 2H), 7.40 (m, 1H), 7.53 (d, J= 8.4 Hz, 1H), 7.63 (d, 7= 8.4 Hz, 2H), 7.85 (d, 8.4 Hz, 2H), 7.94 (d, J= 8.4 Hz, 1H), 10.92 (s, 1H); 19F-NMR (376 MHz, DMSO-Patent; GLAXO GROUP LIMITED; WANG, Yonghui; CAI, Wei; LIU, Qian; MENG, Qinghua; CHENG, Yaobang; YANG, Ting; ZHANG, Guifeng; XIANG, Jianing; WU, Chengde; WO2013/29338; (2013); A1;,
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Related Products of 175278-17-8, These common heterocyclic compound, 175278-17-8, name is 2-Bromo-4-(trifluoromethoxy)aniline, 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: Triphosgene (0.09 g, 0.3 mmol) was dissolved in anhydrous CH2Cl2 (15 mL) and the mixture was stirred on the ice-bath for 15 min. 3-Bromo-5-(trifluoromethyl)aniline (0.16 g, 0.7 mmol) in anhydrous CH2Cl2 (10 mL) was added dropwise to the above mixture and stirring continued for 20 min. Et3N (0.12 mL, 0.89 mmol) diluted with CH2Cl2 (5 mL) was then added into the mixture. Stirring was continued for 20 min and a solution of Et3N (0.12 mL, 0.89 mmol), compound (9) (0.2 g, 0.74 mmol) in anhydrous CH2Cl2 (20 mL) was added. After completion of the action, the reaction was quenched with dilute Na2CO3. The organic layer was washed with water and brine, and dried over Na2SO4. After filtration and concentration in vacuo, the residues was purified by silica gel flash chromatography (PE/AcOEt = 3:1) yielding (W1).

The synthetic route of 175278-17-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Su, Ping; Wang, Jinfeng; Shi, Yaling; Pan, Xiaoyan; Shao, Ruili; Zhang, Jie; Bioorganic and Medicinal Chemistry; vol. 23; 13; (2015); p. 3228 – 3236;,
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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. 103291-07-2, name is 4-Bromo-1-fluoro-2-methoxybenzene, A new synthetic method of this compound is introduced below., category: ethers-buliding-blocks

To a solution of 5-bromo-2-fluoroanisole (200 mg, 0.98 mmol, 1 equiv) in anhydrous THF was added granules of magnesium (24 mg, 0.98 mmol, 1 equiv) under nitrogen. The mixture was heated to 60 C for 2 h. After reaching room temperature, 6-bromopyridin-2-yl carboxaldehyde (182 mg, 0.98 mmol, 1 equiv) was added and the reaction mixture was heated to 80 C and stirred overnight at 80 C. The reaction was cooled to room temperature, quenched with brine and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and concentrated to dryness under vacuum. The product was used in the next step without further purification. C13H11BrFNO2; MW 312.

The synthetic route of 103291-07-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wetzel, Marie; Gargano, Emanuele M.; Hinsberger, Stefan; Marchais-Oberwinkler, Sandrine; Hartmann, Rolf W.; European Journal of Medicinal Chemistry; vol. 47; 1; (2012); p. 1 – 17;,
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Electric Literature of 37895-73-1, These common heterocyclic compound, 37895-73-1, name is 1,2-Dibromo-4,5-dimethoxybenzene, 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 Schlenk flask was charged under argon with 1 equiv of dihaloarene, 0.2 equiv of CuI, 0.22 equiv of Cy3PHBF4, and 0.1 equiv of PdCl2(PPh3)2. The flask was closed, evacuated, and filled with argon (the procedure was repeated thrice), 8 mL of DMF (per millimole of dihaloarene), 4 equiv of triethylamine, and 3 equiv of lactone 1a or 1b were added with a syringe, and the mixture was heated for 8 h at 100C. The mixture was cooled and concentrated under reduced pressure, and the products were isolated by column chromatography using heptane-ethyl acetateas eluent.

The synthetic route of 37895-73-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ghochikyan; Samvelyan; Galstyan; Gevorgyan; Vardanyan; Grigoryan; Langer; Russian Journal of Organic Chemistry; vol. 53; 12; (2017); p. 1833 – 1839; Zh. Org. Khim.; vol. 53; 12; (2017); p. 1797 – 1803,7;,
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Reference of 17061-62-0, 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. 17061-62-0, name is Bis(4-methoxybenzyl)amine, This compound has unique chemical properties. The synthetic route is as follows.

1.3 Preparation of 2-Amino-4-chloro-6-di-(4-methoxybenzyl)amino-5-pyrimidine Carbaldehyde 2-Amino-4,6-dichloro-5-pyrimidine carbaldehyde (0.50 g; 2.60 mmol) was stirred in dry DCM (5 ml). Triethylamine (0.263 g; 2.60 mmol) and di(4-methoxybenzyl)amine (0.669 g; 2.60 mmol) were added and the reaction stirred at r.t for 1.25 h. the reaction was worked up by addition of further DCM (50 ml) and extraction with saturated sodium chloride solution (3*50 ml). The organic layer was washed with water (50 ml), dried (MgSO4) and evaporated yielding a yellow foam (0.957 g; 2.32 mmol; 89.2%).

The chemical industry reduces the impact on the environment during synthesis Bis(4-methoxybenzyl)amine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Cancer Research Campaign Technology Limited; US6677345; (2004); B1;,
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Electric Literature of 17061-62-0,Some common heterocyclic compound, 17061-62-0, name is Bis(4-methoxybenzyl)amine, molecular formula is C16H19NO2, 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 N,N-bis(4-methoxybenzyl)amine (Intermediate EEl 1; 200 g, 775.19 mmol) in DCM (2.5 L) was added Et3N (336.17 mL, 2325.5 mmol), andthe reaction mixture was cooled to 0 C. Ethanesulfonyl chloride ( 95 mL,1007.75 mmol) was added in drop-wise manner followed by DMAP (19.0 g,155.03 mmol). The resulting reaction mixture was stirred at ambient temperaturefor 30 mm. The reaction was monitored by TLC and upon completion, themixture was diluted with H20 and the layers were separated and the aqueousphase was extracted with DCM (3 x 1.5 L). The combined organic layer waswashed with H20, brine, and dried over Na2504. The solvent was removed under reduced pressure to afford the cmde material which was purified by column chromatography over 5i02 gel (100-200 mesh), eluting with a gradient of 0-12% EtOAc in hexane affording the title compound (145 g, 5 3.4%) as a white fluffy solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Bis(4-methoxybenzyl)amine, its application will become more common.

Reference:
Patent; AMGEN INC.; HARRINGTON, Paul E.; ASHTON, Kate; BROWN, Sean P.; KALLER, Matthew R.; KOHN, Todd J.; LANMAN, Brian Alan; LI, Kexue; LI, Yunxiao; LOW, Jonathan D.; MINATTI, Ana Elena; PICKRELL, Alexander J.; STEC, Markian M.; TAYGERLY, Joshua; (991 pag.)WO2018/183418; (2018); 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. 3401-47-6, name is 1-Bromo-2-methoxynaphthalene, This compound has unique chemical properties. The synthetic route is as follows., name: 1-Bromo-2-methoxynaphthalene

In a glove box, 1.0 mmol of 1-bromo-2-methoxynaphthalene, 2.0 mmol of aryl boronic acid, Pd2 (dba) 3, phosphine ligand and 3.0 mmol of potassium phosphate were charged in 7 mL of anhydrous toluene under nitrogen , And the temperature was raised to 80 C, and the reaction was carried out for a period of time. The results are shown in Table 2 below.The amount of Pd2 (dba) 3 and the phosphine ligand is divided into two kinds: (1) 0.25 mol% Pd2 (dba) 3, 0.5 mol% phosphine ligand, or (2) 0.5 mol% Pd2 (dba) mol% phosphine ligand, depending on the amount of ligand used in Table 2.

According to the analysis of related databases, 3401-47-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sun Yat-sen University; Qiu Liqin; Yu Sifan; Zhou Xiantai; (23 pag.)CN106995461; (2017); A;,
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Adding a certain compound to certain chemical reactions, such as: 1663-61-2, name is (Triethoxymethyl)benzene, belongs to ethers-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 1663-61-2, SDS of cas: 1663-61-2

General procedure: Method B (synthesis of 1,2,4-triazin-6(5H)-ones 2) ? The appropriate alpha-aminocarboxylic acid hydrazide 5 (10 mmol) was added to a mixture of triethyl orthoester (10 mmol), dry xylene (40 mL) and 0.12 g p-TsOH and kept under reflux until the disappearance of the starting hydrazide 5 was completed (2-6 h). After cooling, the mixture was washed with water (30 mL), dried over MgSO4 and then concentrated under reduced pressure. The crude product was purified by column chromatography with silica gel and an eluent of benzene/AcOEt, 1:3 v/v or MeOH/CHCl3, 1:4 v/v.

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

Reference:
Article; Kudelko, Agnieszka; Zielin?ski, Wojciech; Jasiak, Karolina; Tetrahedron Letters; vol. 54; 35; (2013); p. 4637 – 4640;,
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Related Products of 59557-91-4, The chemical industry reduces the impact on the environment during synthesis 59557-91-4, name is 4-Bromo-2-methoxyaniline, I believe this compound will play a more active role in future production and life.

General procedure: To a solution of 3k (300 mg, 1.48 mmol) in anhydrous CH2C12 (15 mL) was added pyridine (0.24 mL, 2.97 mmol) and 1-propanesulfonyl chloride (0.18 mL, 1.63 mmol) under argon, and the mixture was stirred at room temperature for 16 h. After being quenched with 1 N HC1(aq) (1.0 mL), water, and CH2C12 were added, the layers were separated. The combined organic phases were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated. The residue was purified by column chromatography on silica gel (EtOAc/hexane, 10:90 to 15:85) to give 6k (490.1 mg, 99%) as a light yellow oil; ?H NMR (CDC13, 500 MHz) 7.41 (1 H, d, J = 8.6 Hz), 7.08 (1 H, dd, J = 8.3, 2.3 Hz), 7.03 (1 H, d, J = 2.5 Hz), 6.74 (1 H, br) , 3.88 (3 H, s), 3.02-2.98 (2 H, m), 1.83-1.79 (2 H, m), 1.00 (3 H, t, J = 7.4 Hz); ?3C NMR (CDC13, 125 MHz) 149.5, 125.5, 124.2, 121.0, 117.5, 114.3, 56.1, 53.1, 17.1, 12.8.

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, 4-Bromo-2-methoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UNIVERSITY OF HOUSTON SYSTEM; TRUSTEES OF TUFTS COLLEGE; CUNY, Gregory; SUEBSUWONG, Chalada; DEGTEREV, Alexei; (139 pag.)WO2018/183633; (2018); A1;,
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Synthetic Route of 95970-05-1, A common heterocyclic compound, 95970-05-1, name is 2,6-Dibromo-4-methoxyaniline, molecular formula is C7H7Br2NO, 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 solution of 2,6-dibromo-4-methoxyphenylamine (3 g, 10.67 mmol, 1 eq) in 10 ml of toluene cooled at 0° C. are added 6.6 ml of concentrated sulfuric acid and 17.5 ml of H3PO2 50percent (15 eq). To the reaction mixture, sodium nitrite (1.47 mg, 21.35 mmol, 2 eq) is added, and all is stirred at 0° C. for 4.5 h. After neutralization with a sodium hydroxide solution, extraction with diethyl ether is performed. The organic phase is dried over magnesium sulfate, filtered and evaporated to dryness on a rotary evaporator. Purification of the raw product was not necessary (yield 96percent, 2.7 g). C7H6Br2O; MW 264/266/268; 1H-NMR (CDCl3): delta 7.23-7.22 (m, 1H), 6.97 (s, 1H), 6.96 (s, 1H), 3.75 (s, 3H); 13C-NMR: delta 160.8, 126.4, 123.1, 116.5, 55.7; IR: 2925, 1599, 1569, 1464 1/cm

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; Hartmann, Rolf; Frotscher, Martin; Oberwinkler, Sandrine; Ziegler, Erika; Messinger, Josef; Thole, Heinrich-Hubert; US2010/204234; (2010); A1;,
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