Tag: M.W=200-300

These common heterocyclic compound, 588-96-5, name is p-Bromophenetole, 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. COA of Formula: C8H9BrO

General procedure: CS127 was prepared using a modified literature procedure [16]. A solution of butyllithium (1. hexane, 0.15 mL) was added to a solution of 4-bromotoluene (8.52 mg, 0.050 mmol) in hexane (15 mL). After stirring for 1 h, N,N’-diisopropylcarbodiimide (6.29 mg, 0.050 mmol) was added dropwise. The solution was stirred for 1 h at room temperature and then the dimer [(FMeppy)2Ir(mu-Cl)]2 (30 mg, 0.025 mmol) was added. The mixture was heated overnight at 70 C. After being cooled to room temperature, the resulting precipitate was collected and washed with diethyl ether. The dried product was obtained as a yellow powder. Yield 65%.

The synthetic route of p-Bromophenetole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sahin, Cigdem; Goren, Aysen; Varlikli, Canan; Journal of Organometallic Chemistry; vol. 772; (2014); p. 68 – 78;,
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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. 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane, This compound has unique chemical properties. The synthetic route is as follows., Safety of 1-Bromo-2-(2-bromoethoxy)ethane

Step 1 ): (0666) To 200 mg (0.984 mmol) of (R)-6-(4-aminophenyl)-5-methyl-4,5-dihydropyridazin-3(2H)-one dissolved in 1 mL of DMF was added 250 muIota_ (2.00 mmol) of bis (2-bromoethyl) ether and 400 mg of K2CO3 and the mixture was stirred overnight at 60 C. The next day another 250 muIota_ of bis (2- bromoethyl) ether and 170 mg of K2CO3 was added. After 3 h, EtOAc and water were added, the water was rinsed with EtOAc, the combined EtOAc washes were dried and concentrated. Chromatography with 0-4% MeOH in CH2C12 yielded 125 mg of product Compound 3 (46%). 1H NMR (300 MHz, CDCI3) delta 8.61 (s, 1 H), 7.68 (d, J = 8.8, 2H), 6.92 (d, J = 8.8, 2H), 3.99 – 3.76 (m, 4H), 3.44 – 3.31 (m, 1 H), 3.29 – 3.22 (m, 4H), 2.70 (dd, J = 6.7, 16.8, 1 H), 2.46 (d, J = 16.7, 1 H), 1 .24 (d, J = 7.3, 3H). 13C NMR (75 MHz, CDCI3) delta 1 66.64, 154.05, 152.18, 127.1 0, 125.33, 1 14.73, 66.69, 48.33, 33.93, 27.94, 1 6.36. MS: 274 (M + 1 ). Anal. Calcd. for C15H19N3O2: C, 65.91 ; H, 7.01 ; N, 15.37; Found. 65.81 , H, 6.66, N, 15.26.

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 5414-19-7.

Reference:
Patent; THE BROAD INSTITUTE, INC.; DANA-FARBER CANCER INSITUTE, INC.; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; LEWIS, Timothy, A.; WU, Xiaoyun; GREULICH, Heidi; MEYERSON, Matthew; ELLERMANN, Manuel; LIENAU, Philip; EIS, Knut; WENGNER, Antje, Margret; KOPITZ, Charlotte, Christine; LANGE, Martin; (88 pag.)WO2018/141835; (2018); A1;,
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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 143-24-8 as follows. Computed Properties of C10H22O5

The bis (trifluoromethylsulfonyl) imide lithium described in(Hereinafter referred to as LiNTf 2) and G 4 or G 3 Bu were weighed in amounts listed in Table 1 and placed in a 50 mL round bottom flask,In this case, the mixture was stirred at 20 C. for 6 hours under a nitrogen atmosphere to obtain a single phase colorless transparent liquid without phase separation.

According to the analysis of related databases, 143-24-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KANEKA CORPORATION; SAITO, KEN; (13 pag.)JP2016/6022; (2016); A;,
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Electric Literature of 116557-46-1, A common heterocyclic compound, 116557-46-1, name is 3-Bromo-2-methoxyaniline, molecular formula is C7H8BrNO, 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.

This material (1.8 g) is taken up in methanol (100 ml) containing concentrated hydrochloric acid (0.6 ml), treated with 10% palladium on carbon and hydrogenated at 45 psi for 8 hours. The catalyst is filtered off and the solvent removed at reduced pressure to afford 4-tert-butoxypiperidine hydrochloride.

The synthetic route of 116557-46-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CIBA-GEIGY AG; EP475895; (1992); A1;,
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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. 17715-69-4, name is 1-Bromo-2,4-dimethoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 17715-69-4

General procedure: A suspension of Pd2(dba)3 (6.9mg, 0.0075mmol), tBu3PHBF4 (8.7mg, 0.03mmol), KOH (42mg, 0.75mmol), aryl bromide 4 (0.36mmol) and tetralone 3 (0.3mmol) in a mixture of dioxane/water (4:1, v/v, 3mL) was degassed and heated under Ar and microwave irradiation (80W of initial power, 100°C, 40min, infrared probe). Then, the mixture was allowed to cool to rt, diluted in AcOEt, washed with saturated NH4Cl solution, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude material was purified by silica gel chromatography. Dioxane quality is extremely important for the success of the reaction. Characterization of alpha-aryl-alpha-tetralones is given in Ref.[26].

The synthetic route of 17715-69-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Fernandes, Talita de A.; Costa, Paulo R. R.; Manvar, Dinesh; Basu, Amartya; Kaushik-Basu, Neerja; Domingos, Jorge L. O.; Nichols, Daniel Brian; European Journal of Medicinal Chemistry; vol. 112; (2016); p. 33 – 38;,
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Some common heterocyclic compound, 4698-11-7, name is 10-Methoxy-5H-dibenzo[b,f]azepine, molecular formula is C15H13NO, 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. Recommanded Product: 10-Methoxy-5H-dibenzo[b,f]azepine

EXAMPLE I; Preparation of 5,11-Dihydro-10H-dibenz[b,f]azepine-10-one (Oximinostilbene) IV; A 2-L, three-necked flask equipped with a mechanical stirrer, thermometer and nitrogen inlet was charged with 10-methoxyiminostilbene I (110.0 g, 0.49 mol) and 330 mL acetone. A 10% solution of hydrochloric acid (28.6 g, 0.08 mol) was then added. The reaction mixture was stirred at ambient temperature for 1-1.5 hours until reaction completion. The product was precipitated by the addition of 660 mL of deionized water, and the resulting suspension was stirred for 3-4 hours. The suspension was filtered and washed with water. After drying, oximinostilbene (99.92 g, 97%) was obtained as a bright yellow solid having a purity of 99% by HPLC. 1H NMR (CDCl3, d): 3.80, 6.87, 7.04-7.15, 7.22-7.24, 7.32-7.37, 8.04 ppm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4698-11-7, its application will become more common.

Reference:
Patent; Apotex Pharmachem Inc.; US2005/282797; (2005); A1;,
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Adding a certain compound to certain chemical reactions, such as: 5111-65-9, name is 2-Bromo-6-methoxynaphthalene, 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 5111-65-9, Computed Properties of C11H9BrO

6-Methoxy-2-naphthaldehyde ((a) Harvey, R. G.; Cortez, C.; Sawyer, T. W.; DiGiovanni, J.; J. Med. Chem. 1988, 31, 1308-1312. (b) Harvey, R. G.; Cortez, C. Tetrahedron, 1997, 53, 7101-7118) was prepared by formylation (Beringer, F. M.; Nathan, R. A. J. Org. Chem. 1969, 34, 685-689) of 6-methoxy-2-bromonaphthalene in 53% yield.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-6-methoxynaphthalene, and friends who are interested can also refer to it.

Reference:
Patent; University of Pittsburgh; US6706839; (2004); B1;,
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Synthetic Route of 54314-84-0, A common heterocyclic compound, 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene, molecular formula is C10H13BrO, 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.

Step A: methyl 2-cyanoacetate (23 g, 232 mmol) was addeddropwise to a suspension of sodium hydride (60percent, 2.79 g,69.7 mmol) in DMF (100 mL) and THF (100 mL) at 0 C, and thereaction mixture was warmed to rt and stirred at rt for 30 min.((2-Bromoethoxy)methyl)benzene (10 g, 46.5 mmol) was added,and the reaction mixture was stirred at rt for 12 h. Water wasadded and the aqueous layer was extracted with ether (3). Thecombined organic layers were washed with brine, dried over anhydroussodium sulfate, and filtered, and the filtrate was evaporatedto give the crude product. Excessive methyl 2-cyanoacetate wasremoved by distillation under high vacuum at 120?130 C, andremaining residue was purified by silica gel chromatography elutingwith 0?50percent EtOAc/hexanes to give methyl 4-(benzyloxy)-2-cyanobutanoate (8 g, 74percent) as a colorless liquid. 1H NMR(300 MHz, CDCl3) d 7.3 (m, 5H), 4.51 (s, 2H), 3.70 (s, 3H), 3.6?3.9(m, 3H), and 2.3 (m, 2H). LC/MS m/z: (M+H)+ calcd forC13H16NO3, 234.11; found 234.4. Step B: To a suspension of sodiumhydride (60percent, 9 g, 225 mmol) in THF (170 mL) and DMF (170 mL)was added methyl 4-(benzyloxy)-2-cyanobutanoate (35 g,150 mmol) at 0 C, and the reaction mixture was stirred at rt for30 min. ((3-Bromopropoxy)methyl)benzene (37.8 g, 165 mmol)was added, and the reaction mixture was stirred at rt for 12 h.Water was added and the aqueous layer was extracted with ether(3). The combined organic layers were washed with brine, driedover anhydrous sodium sulfate, and filtered, and the filtrate wasevaporated to give the crude product. The crude product was purifiedby silica gel chromatography eluting with 0?40percent EtOAc/hexanesto give 22 (40 g, 70percent) as a colorless oil. 1H NMR (400 MHz,CDCl3) d 7.3 (m, 10H), 4.48 (2H, s), 4.47 (2H, s), 3.7 (m, 2H), 3.57(3H, s), 3.48 (m, 1H), 2.42 (m, 1H), 1.8?2.1 (m, 4H), and 1.6 (m,1H). LC/MS m/z: (M+H)+ calcd for C23H28NO4, 382.20; found 382.4.

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; Wu, Yong-Jin; Guernon, Jason; McClure, Andrea; Luo, Guanglin; Rajamani, Ramkumar; Ng, Alicia; Easton, Amy; Newton, Amy; Bourin, Clotilde; Parker, Dawn; Mosure, Kathleen; Barnaby, Omar; Soars, Matthew G.; Knox, Ronald J.; Matchett, Michele; Pieschl, Rick; Herrington, James; Chen, Ping; Sivarao; Bristow, Linda J.; Meanwell, Nicholas A.; Bronson, Joanne; Olson, Richard; Thompson, Lorin A.; Dzierba, Carolyn; Bioorganic and Medicinal Chemistry; vol. 25; 20; (2017); p. 5490 – 5505;,
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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. 32338-02-6, name is 2-Bromo-4-methoxyaniline, A new synthetic method of this compound is introduced below., Formula: C7H8BrNO

General procedure: A mixture of benzyl 1-oxa-6-azaspiro[2.5]octane-6-carboxylate (247 mg, 1.0 mmol), 2-bromo-4-methoxyaniline (303 mg, 1.5 mmol) and lithium perchlorate (190 mg, 1.7 mmol) were taken in acetonitrile (3.0 mL). The reaction mixture was heated to 90 °C for 18 h. The reaction mixture was diluted with ethyl acetate (20 mL) and washed with water. The organic layer was dried over sodium sulfate and concentrated under reduced pressure, and the product was purified by column chromatography (silica gel, 50percent EtOAc/hexanes) to provide benzyl 4-(((2-bromo-4-methoxyphenyl)amino)methyl)-4-hydroxypiperidine-1-carboxylate, 5c (358 mg, 80percent) as a colourless syrup.

The synthetic route of 32338-02-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kurissery, A. Tony; Rajkumar, G. Abraham; Arvapalli, Venkata Satyanarayana; Pitchumani, Venkatachalam; Tetrahedron Letters; vol. 58; 37; (2017); p. 3607 – 3611;,
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Synthetic Route of 38380-85-7, 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. 38380-85-7 name is 1-Bromo-4-cyclopropoxybenzene, 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.

General procedure: A mixture of 2,4-dibromothiazole (Compound 8A) (3.9 g, 16 mmol), 3,4- dichlorophenylboronic acid (3.05 g, 16 mol), Pd(dppf)C12 (0.7 g, 0.87 mmol), and cesium carbonate (15 g, 46 mmol) in DME (120 mL) and water (10 mL) was heated at reflux under nitrogen overnight. The reaction mixture was diluted with water (100 mL) and extracted with ethyl acetate (200 mL x 2). The combined extracts were washed with water (200 mL) and brine (200 mL), dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified with flash column chromatography on silica gel (ethyl acetate in petroleum ether, from 0% to 10% v/v) to yield Compound 8B. LC-MS (ESI) m/z: 308 [M+H]t

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-4-cyclopropoxybenzene, and friends who are interested can also refer to it.

Reference:
Patent; BIOMARIN PHARMACEUTICAL INC.; WANG, Bing; CHAO, Qi; (737 pag.)WO2019/133770; (2019); A2;,
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