Tag: M.W=200-300

74137-36-3, name is 1,3-Dibromo-5-methoxybenzene, belongs to ethers-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. name: 1,3-Dibromo-5-methoxybenzene

General procedure: Typically, TDPP (200 mg, 0.27 mmol), dibromobenzene derivatives 0.11 mmol, anhydrous Cs2CO3(200 mg, 0.61 mmol), PivOH (7.9 mg, 0.08 mmol), Pd2(dba)3 (4.00 mg, 1.5 mol%), tris(o-methoxyphenyl)phosphine (3.08 mg, 3 mol%) were successively added into a Schlenk tube. The tube was purged by three repetitions of vacuum and argon filling. Then, 5 mL anhydrous toluene was added via syringe.The reaction solution was deoxygenated using three freeze-vacuum-thaw cycles, and then rigorouslystirred at 100 C for 24 h under argon atmosphere. Removal of the toluene by rotary evaporatoraorded the crude product, which was then purified by chromatogragh column (CC) on silica gelusing a mixture of CH2Cl2 and hexane as eluent, giving the target molecules Ms1~9.

The synthetic route of 74137-36-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liu, Hui; Zhang, Xiao-Feng; Cheng, Jing-Zhao; Zhong, Ai-Guo; Wen, He-Rui; Liu, Shi-Yong; Molecules; vol. 24; 9; (2019);,
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Adding a certain compound to certain chemical reactions, such as: 1462-37-9, name is ((2-Bromoethoxy)methyl)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 1462-37-9, Safety of ((2-Bromoethoxy)methyl)benzene

[00405] Step A: To a solution of ((2-bromoethoxy)methyl)benzene (1.34 mL, 7.6 mmol) in diethyl ether (20 mL) were added magnesium turnings (0.185 g, 7.6 mmol) and the mixture was heated at reflux for 30 min. The mixture was cooled to -20 0C, and a solution of (4-(lH-pyrazol-5-ylamino)pyirolo[l,2-f][l,2,4]triazin-2-yichi4- fiuorophenyl)methanone (700 mg, 2.17 mmol) in THF (20 mL) was added. The mixture was stirred at -20 °C for 1 hour, then aqueous ammonium chloride was added, and the precipitated solid was collected by filtration, washing with water. The crude solid was purified using chromatography on silica gel eluting with 2-8percent MeOH/DCM to afford 1 -(4-( 1 H-pyrazol-5-ylamino)pyrrolo [ 1 ,2-fJ [ 1 ,2,4]triazin-2-yl)-4- (benzyloxy)-l-(4-fluorophenyl)butan-l-ol (625 mg, 85percent).

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Reference:
Patent; AMBIT BIOSCIENCES CORPORATION; ABRAHAM, Sunny; CHAO, Qi; HADD. Michael, J.; HOLLADAY, Mark, W.; LIU, Gang; NAMBU, Mitchell, D.; SETTI, Eduardo; WO2010/2472; (2010); A1;,
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Adding a certain compound to certain chemical reactions, such as: 402-07-3, name is 4-Bromo-3-methoxybenzotrifluoride, 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 402-07-3, Recommanded Product: 402-07-3

General procedure: A microwave vial was charged with N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (28) (0.100 g, 0.24 mmol), xantphos (0.028 g, 0.048 mmol), 4-bromo-3-methoxybenzonitrile (0.051 g, 0.24 mmol), Pd2(dba)3 (0.022 g, 0.024 mmol) and sodium tert-butoxide (0.046 g, 0.48 mmol). The mixture was diluted with toluene (2.5 mL), purged with nitrogen, and heated at 130 C in the microwave for 30 min. After completion, the mixture was cooled to room temperature and trifluoroacetic acid (1.0 mL) was added. After stirring for 45 min at room temperature, the reaction was filtered through a plug of Celite, washing with DCM 10 mL). The filtrate was concentrated and purified by reverse-phase preparative HPLC using 0.1% TFA in CH3CN/H2O, gradient 25% to 90% over 15 min to provide 4-(4-cyano-2-methoxyphenyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide 10 as a salt with trifluoroacetate (0.073 g, 0.14 mmol, 56 % yield) as an orange solid.

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Reference:
Article; La, Daniel S.; Peterson, Emily A.; Bode, Christiane; Boezio, Alessandro A.; Bregman, Howard; Chu-Moyer, Margaret Y.; Coats, James; DiMauro, Erin F.; Dineen, Thomas A.; Du, Bingfan; Gao, Hua; Graceffa, Russell; Gunaydin, Hakan; Guzman-Perez, Angel; Fremeau, Robert; Huang, Xin; Ilch, Christopher; Kornecook, Thomas J.; Kreiman, Charles; Ligutti, Joseph; Jasmine Lin, Min-Hwa; McDermott, Jeff S.; Marx, Isaac; Matson, David J.; McDonough, Stefan I.; Moyer, Bryan D.; Nho Nguyen, Hanh; Taborn, Kristin; Yu, Violeta; Weiss, Matthew M.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 15; (2017); p. 3477 – 3485;,
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Some common heterocyclic compound, 19056-40-7, name is 4-Bromo-3-methoxyaniline, molecular formula is C7H8BrNO, 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: 4-Bromo-3-methoxyaniline

POCl3 (5.07 ml, 54.4 mmol) was added to a mixture of 4-bromo-3-methoxyaniline (10 g, 49.5 mmol) and malonicacid (5.15 g, 49.5 mmol) with thorough mixing, and the solution was then heated to 105°C. After 5 min, the reactionbegan to bubble vigorously and eventually formed a hard foam, and heating was continued for 1 h. After cooling, water(200 mL) was added, and the mixture was stirred for 30 min. The solid was filtered off and washed with water. 2N NaOH(300 mL) was added to the solid, and stirring was continued overnight. The remaining solid was filtered off. EtOH (5 mL)was then added to the filtrate, and the basic layer was then acidified with concentrated HCl to pH 2. The resulting solidwas then filtered off and washed with water. The solid was then transferred to a flask, and the remaining water wasremoved by stripping off EtOH (200 mL x 2). The solid was then further dried under high vacuum for 15 h to yield 8.75g (66percent) of the title compound as an off-white solid. LRMS ESI+ (M+H)+ 270.2/272.2

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 19056-40-7, its application will become more common.

Reference:
Patent; Merck Sharp & Dohme Corp.; MSD Italia S.r.l.; MCCAULEY, John, A.; LIVERTON, Nigel, J.; HARPER, Steven; MCINTYRE, Charles, A.; RUDD, Michael, T.; (73 pag.)EP2268285; (2018); B1;,
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Reference of 7025-06-1, A common heterocyclic compound, 7025-06-1, name is 1-Bromo-2-phenoxybenzene, molecular formula is C12H9BrO, 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.

Preparation of intermediate C01-A: 1-bromodiphenyl ether (2.49 g, 0.01 mol) was dissolved in 100 mL of dry tetrahydrofuran under nitrogen atmosphere, when the internal temperature of the system was lowered to -75 C,Slowly add 4.8 mL of n-hexane solution of n-butyllithium (2.5 mol/L).After the completion of the dropwise addition, the reaction was kept at -75 C for 2 h, and the temperature was maintained.Add 9,9-dimethyl-5H,9H-quinoline[3,2,1-de]acridone solid(2.80g, 0.009 mol), add the insulation reaction for 2h, keep warm,The reaction was continued at room temperature for 2 h, after which 70 g of a 10% by mass dilute hydrochloric acid was added dropwise.Stir for 1 h, separate the liquid, collect the organic phase, remove the solvent, and obtain 5 g of oil;Further, 60 g of glacial acetic acid and 1.0 g of concentrated hydrochloric acid having a concentration of 36.5 wt% were added to the obtained oil.The temperature was raised to reflux, the reaction was kept for 5 hours, the temperature was lowered to 25 C, and 50 g of toluene and 100 g of water were added.The liquid phase is separated, the organic phase is desolvated, the crude oil is passed through a silica gel column, and the petroleum ether is rinsed. The column liquid containing a single product component is collected, and 50 g of petroleum ether is beaten after desolvation, and the filter cake is collected by suction filtration.Obtaining intermediate C01-A,White solid powder 2.52g,Yield 60.4%.

The synthetic route of 7025-06-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CECEP Wanrun Co., Ltd.; Gao Shukun; Zhang Jiangfeng; Sheng Lei; Li Peng; Ma Yongjie; Qin Yuhu; (20 pag.)CN109970775; (2019); 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. 168268-00-6, name is 4-(Benzyloxy)-3-fluoroaniline, A new synthetic method of this compound is introduced below., name: 4-(Benzyloxy)-3-fluoroaniline

4-Benzyloxy-3-fluoro-aniline (55 g), isopropyl alcohol (550 ml) and (R)-glycidyl butyrate (36.6 g) were taken into a reaction flask at room temperature (25-30C), and the resulting mass was heated to reflux and then stirred for 28 hours at the same temperature. After completion of the reaction, the solvent was distilled under vacuum to obtain a residue. Diisopropyl ether (560 ml) was added to the residue at the room temperature and theresulting solution was heated to reflux, followed by stirring for 15 minutes at the same temperature. The reaction mass was cooled to 25-30C and then stirred for 30 minutes at the same temperature. The separated solid was filtered and then washed with diisopropyl ether (100 ml) to produce 62 g of (2R)-3-(4-benzyloxy-3-fluoro-phenylamino)-2-hydroxy- propyl butanoate (Purity by HPLC: 98.6%).

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; SYMED LABS LIMITED; MOHAN RAO DODDA; MALLA REDDY VANGA; JITHENDER AADEPU; (95 pag.)WO2016/79757; (2016); A2;,
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Reference of 873980-68-8, 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 873980-68-8 as follows.

Preparation of 6-bromo-5-methybenzoxazole (43): To a suspension of 4-bromo-6-methoxy-3-methylaniline (41) (500 mg, 2.3 mmol) in 6 ml DCM was added 1 M BBr3 in DCM (4.6 ml, 4.6 mmol). The reaction mixture was stirred at r.t. for 2 h, which turned to a brown solution and back to a brown suspension. After quenched with aq. sodium bicarbonate solution, the mixture was extracted with EA. The org. phase was washed with brine, dried over sodium sulfate, concentrated to dryness to give 581 mg 2-amino-5-bromo-4-methylphenol as dark oil.A mixture of 2-amino-5-bromo-4-methylphenol (42) (290 mg), trifluoromethanesulfonic acidYtterbium (III) salt (20 mg) and trimethyl orthoformate (185 mul, 1.5 eq.) in 2 ml EtOH was heated at 90 C. for 2 h. After cooling down to r.t., the reaction mixture was taken up in EA, washed with aq. NaHCO3 and brine, dried over Na2SO4, concentrated to dryness. The resulting brown solid was dissolved in DCM and subjected to silica gel column purification using 0-60% B (A: hexane; B: 50% EA in hexane) to furnish 91.9 mg 6-bromo-5-methylbenzoxazole (43) as yellow solid (yield: 38%)

According to the analysis of related databases, 873980-68-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CalciMedica, Inc.; US2011/263612; (2011); A1;,
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Reference of 31804-36-1, 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. 31804-36-1, name is 1-Bromo-3-methoxy-2-methylbenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 4-bromo-l-methoxy-2-(3-methoxypropoxy)benzene (11.0 g, 54.7 mmol) in THF (120 mL) was added l-(2-thienyl)ethanone (8.97 g, 71.1 mmol), i-BuONa (7.89 g, 82.1 mmol), Pd2(dba)3 (1 g, 1.09 mmol) and Xantphos (633 mg, 1.09 mmol ) under nitrogen atmosphere. The mixture was heated at 50 C for 4 hrs, and then concentrated under reduced pressure. The residue was diluted with DCM (600 mL). The resulting organic mixture was washed with water and brine, dried over anhydrous Na2S04 and concentrated under reduced pressure. The residue was purified by column chromatography to afford 2-(3-methoxy-2-methyl- phenyl)-l-(2-thienyl)ethanone (13.0 g) as a brown oil.

The synthetic route of 1-Bromo-3-methoxy-2-methylbenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HAN, Xingchun; JIANG, Min; YANG, Song; (109 pag.)WO2016/128335; (2016); A1;,
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Related Products of 36805-97-7,Some common heterocyclic compound, 36805-97-7, name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, molecular formula is C11H25NO2, 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 suspension of 2,6-dichloroisonicotinic acid (5.23 g, 27.24 mmol) in toluene (100 mL) is heated to 80 C. and then slowly treated with N,N-dimethylformamide di-tert. butylacetal (19.94 g, 98.0 mmol). The mixture becomes slightly yellow and clear. Heating and stirring is continued for 3 h before the solution is cooled to rt, diluted with ether and washed with sat. aq. Na2CO3-solution. The org. extract is dried over MgSO4, filtered and the solvent is evaporated to give 2,6-isonicotinic acid tert.-butyl ester (6.97 g) which solidifies as beige fine needles. 1H NMR (CDCl3): delta 1.60 (s, 6H), 7.73 (s, 1H).

The synthetic route of 36805-97-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Actelion Pharmaceuticals Ltd.; US2010/63108; (2010); A1;,
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Synthetic Route of 104197-14-0, 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. 104197-14-0, name is 4-Bromo-2,6-difluoroanisole belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example A5; 4-(3,5-Difluoro-4-(l-(4-(trifluoromethyl)benzyl)azetidin-3-yloxy)phenyl)-l-(methylsulfonyl)piperidineineA5g Example A5[0022] Step A: In a microwave vial, a mixture of pyridin-4-ylboronic acid (160 mg, 1.3 mmol), 5-bromo-l,3-difluoro-2-methoxybenzene A5a (223 mg, 1 mmol) and Pd(PPh3)4 (58 mg, 0.05 mmol) is dissolved/suspended in dimethylformamide (3 mL). To the mixture are added cesium carbonate (978 mg, 3 mmol) and water (3 mL). The vial is sealed and subjected to microwave irradiation (150 C, 15 min). The mixture is filtered through a syringe filter and washed with ethyl acetate. Water is added and the mixture extracted with ethyl acetate (4x). The organic phase is dried over sodium sulfate and concentrated. The crude material is purified by flash chromatography (ethylacetate/hexanes gradient) to afford 4-(3,5-difluoro-4-methoxyphenyl)pyridine A5b as a white solid: 1H-NMR (400 MHz, CDC13) delta 8.69 (d, J= 6 Hz, 2 H), 7.44 (d, J= 6 Hz, 2H), 7.22 (d, J = 9.6 Hz, 2H), 4.09 (s, 3H); MS calcd. for C12Hi0F2NO ([M+H]+): 222.1, found: 222.1.

The synthetic route of 4-Bromo-2,6-difluoroanisole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IRM LLC; AZIMIOARA, Mihai; COW, Christopher; EPPLE, Robert; LELAIS, Gerald; MECOM, John; NIKULIN, Victor; WO2011/44001; (2011); A1;,
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