Category: ethers-buliding-blocks

Electric Literature of 702-24-9, A common heterocyclic compound, 702-24-9, name is 4-Methoxy-N-methylbenzylamine, molecular formula is C9H13NO, 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.

A mixture of 3-(3-amino-4-fluorophenyl)-7-chloro-1-isopropyl-1,6-naphthyridin-2(1H)-one (4 g, 12.1 mmol) and (4-methoxybenzyl)methylamine (15 mL) was degassedunder reduced pressure, then heated to 180C under N2 for 4 h. After cooling, the reactionmixture was diluted with Et20. The precipitate was filtered, washed with Et20 and dried invacuo to giVe 3-(3-amino-4-fluoro-phenyl)-1-isopropyl-7-[( 4-methoxybenzyl)-methylamino]-1H-[1,6]naphthyridin-2-one (5.3 g) as a solid contaminated with (4-methoxybenzyl)methylamine HCl salt.

The synthetic route of 702-24-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FLYNN, Daniel L.; KAUFMAN, Michael D.; WO2013/184119; (2013); A1;,
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Reference of 16618-68-1, These common heterocyclic compound, 16618-68-1, name is 3-Bromo-5-methoxyaniline, 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.

In 50 ml by adding three-necked bottle 1.01g3-methoxy-5-bromoaniline(5mmol), 1.40g (5.5mmol) connecting boric acid frequency ester, 1.47g (15mmol) and potassium acetate PdCl2(dppf) catalyst (150 mg), vacuum pumping and nitrogen injection 6 times, the state of the protection of nitrogen by adding DMSO (25 ml), 80 C reaction 18h, in a water cooling retrodisplacement, precipitate after filtering, washing, drying to obtain the crude column chromatography separation (petroleum ether: ethyl acetate = 1:5) shall be 1.03g yellow powdery solid, yield 82.4%.The 0.99g the above-mentioned preparation of the compound (4mmol) by adding 100 ml round-bottom flask, add 30 ml of methanol is dissolved, add 0.56gNH4Cl (10mmol), constant voltage dropping funnel for slowly dripping 2.56gNaIO4(12mmol) of 7 ml aqueous solution, stirring the mixture at room temperature for reaction 18h, TLC detection, filtering to remove the inorganic salt, methanol filters after evaporation to dryness, drying to obtain the crude product purification column chromatography (petroleum ether: ethyl acetate = 1:5) shall be near white powdery solid 0.53g, yield 79.1%.

The synthetic route of 16618-68-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ocean University of China; Jiang, Tao; Yin, ruijuan; Zhang, Li Juan; (38 pag.)CN103497211; (2016); B;,
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Electric Literature of 366-99-4, A common heterocyclic compound, 366-99-4, name is 3-Fluoro-4-methoxyaniline, molecular formula is C7H8FNO, 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.

5-bromo-2-chloro-N-phenylnicotinamide (224 mg, 719 mumol) and 3-fluoro-4- methoxybenzenamine (316.7 mg, 2244 mumol) were suspended in isoamyl alcohol (1.5 ml) in a reaction microwave vessel which was sealed. This vessel was heated in the Biotage Initiator microwave at 200 0C for 20 minutes, with 45 seconds of stirring beforehand, and then cooled to room temperature. This process was repeated using 5-bromo-2-chloro-N-phenylnicotinamide (810 mg, 2.60 mmol) and 3-fiuoro-4- methoxybenzenamine (1.092 g, 7.74 mmol), and isoamyl alcohol (7.5 ml), and then repeated a third time with 5-bromo-2-chloro-N-phenylnicotinamide (1.643 g, 5.28 mmol), 3-fluoro-4-methoxybenzenamine (2.285 g, 16 mmol), and isoamyl alcohol (10 ml). These three sets of reaction were combined, concentrated, treated with Et2psi, and filtered. The solid was washed with Et2O, and the filtrate was concentrated and purified on a silica gel filter (~3 inches, DCM) to afford the desired 5-bromo-2-(3-fluoro-4- methoxyphenylamino)-N-phenylnicotinamide (3.49 g, 8.39 mmol, 75percent yield). MS (ESI pos. ion) m/z: 416 (MH+, 79Br), 418 (MH+, 81Br). Calc’d exact mass for C19H15BrFN3O2: 415 (79Br), 417 (81Br).

The synthetic route of 366-99-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; WO2008/79294; (2008); A1;,
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Some common heterocyclic compound, 38197-43-2, name is 2-Bromo-1-methoxy-3-methylbenzene, molecular formula is C8H9BrO, 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. Formula: C8H9BrO

General procedure: A mixture of 17 (200 mg, 0.369 mmol), 2-bromo-1-methoxy-3-methylbenzene(148 mg, 0.737 mmol), Pd(OAc)2 (8.3 mg, 0.037 mmol), 2-dicyclohexylphosphino-2?,6?-di-isopropoxy-1,1?-biphenyl (34.4 mg,0.074 mmol), and Cs2CO3 (360 mg, 1.11 mmol) in toluene (7.5 ml) and water (1.5 ml) was stirred at 80 C for 25 h. Then, water was added tothe reaction mixture, and the product was extracted with AcOEt. Theorganic layer was successively washed with water and brine, dried overanhydrous Na2SO4 and concentrated in vacuo. The residue was purifiedby silica gel column chromatography (hexane/AcOEt=40/60 to 10/90) to give the title compound as a white solid (43 mg, 21%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 38197-43-2, its application will become more common.

Reference:
Article; Murafuji, Hidenobu; Sugawara, Hajime; Goto, Megumi; Oyama, Yoshiaki; Sakai, Hiroki; Imajo, Seiichi; Tomoo, Toshiyuki; Muto, Tsuyoshi; Bioorganic and Medicinal Chemistry; vol. 26; 12; (2018); p. 3639 – 3653;,
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Related Products of 887268-25-9, 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. 887268-25-9, name is 2-Bromo-4-methyl-1-(trifluoromethoxy)benzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

1-Bromo-5-methyl-2-trifluoromethoxybenzene (1.0 g, 3.92 mmol), bis(pinacolato)diboron (1.49 g, 5.88 mmol), potassium acetate (1.54 g, 15.7 mmol) and 1 ,1′-[bis(diphenylphosphino)ferrocene] dichloropalladium (II) (0.287 g, 0.392 mmol) were combined and stirred in dimethylsulphoxide (25 ml). The reaction flask was purged with nitrogen for 5 minutes before heating to 1000C for 10 hours. The mixture was cooled and partitioned between f¡ãrt-butylmethyl ether (100 ml) and water (100 ml). Insoluble material was removed by filtration then the organic extract dried over anhydrous MgSO4, filtered and evaporated in vacuo to afford the crude title compound as a brown oil (895 mg, 76%). Material was taken on without further purification to next stage.

The synthetic route of 2-Bromo-4-methyl-1-(trifluoromethoxy)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER LIMITED; WO2008/135826; (2008); A2;,
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Related Products of 16452-01-0, 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. 16452-01-0, name is 3-Methoxy-4-methylaniline, This compound has unique chemical properties. The synthetic route is as follows.

full text is not avalable from article

The chemical industry reduces the impact on the environment during synthesis 3-Methoxy-4-methylaniline. I believe this compound will play a more active role in future production and life.

Reference:
Article; Nino, Patricia; Caba, Marta; Aguilar, Nuria; Terricabras, Emma; Albericio, Fernando; Fernandez, Joan-Carles; Indian Journal of Chemistry – Section B Organic and Medicinal Chemistry; vol. 55B; 7; (2016); p. 854 – 881;,
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Related Products of 3616-56-6,Some common heterocyclic compound, 3616-56-6, name is 2,2-Diethoxy-N,N-dimethylethanamine, molecular formula is C8H19NO2, 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.

Synthesis of 3-bromo-12H-benzofuranyl[2,3-a]carbazole (compound 9); (9); Under nitrogen, compound 8 (1 .3 g, 1 eq.) is initially charged and dissolved with acetic acid (55 ml) while heating to reflux. Then (dimethylamino)acetaldehyde diethyl acetal (95percent; 7.1 g, 10 eq.) is added dropwise to the reaction within 1 .5 h and the mixture is stirred at reflux for a further 7 h. It is stirred at room temperature overnight. The next day, it is heated back to reflux and a further 2 g of (dimethylamino)acetaldehyde diethyl acetal are added dropwise. After 6 h at reflux, a further 4 g (dimethylamino)acetaldehyde diethyl acetal are added dropwise and it is stirred for a further 7.5 h. The mixture is cooled to room temperature and diluted with methylene chloride. Washed in a separating funnel with distilled water and then with saturated NaCI. The organic phase is dried with sodium sulfate and concentrated. LC (C18-Si02, acetonitrile) gives 0.33 g of product (24percent yield). 1H NMR (CD2CI2, 400 MHz): “5 = 8.7 (br s, 1 H), 8.15 (d, 2H), 8.06 (d, 1 H), 7.78 (d, 1 H), 7.60 (m, 3H), 7.48 (dd, 1 H), 7.32 (dd, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,2-Diethoxy-N,N-dimethylethanamine, its application will become more common.

Reference:
Patent; BASF SE; BASF (CHINA) COMPANY LIMITED; KONINKLIJKE PHILIPS ELECTRONICS N.V.; OSRAM OPTO SEMICONDUCTORS GMBH; PHILIPS INTELLECTUAL PROPERTY & STANDARDS GMBH; LANGER, Nicolle; SCHILDKNECHT, Christian; WATANABE, Soichi; FUCHS, Evelyn; WAGENBLAST, Gerhard; LENNARTZ, Christian; MOLT, Oliver; DORMANN, Korinna; HUNZE, Arvid; KRAUSE, Ralf; SCHMID, Guenter; HEUSER, Karsten; VAN ELSBERGEN, Volker; BOERNER, Herbert Friedrich; WO2011/125020; (2011); 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. 168268-00-6, name is 4-(Benzyloxy)-3-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C13H12FNO

To a stirred mixture of 4-benzyloxy-3-fluoro-phenylamine (33.7 g, 155.3mmol), 1-(4-fluoro-phenylcarbamoyl)-cyclopropane carboxylic acid (38.13 g, 170.8mmol) and anhydrous DCM (600 ml) was added EDCI (44.7 g, 233.9mmol) in portions. After stirring at r.t. for 1 h, the reaction mixture was diluted with saturated sodium bicarbonate (400 ml) and stirred for 30 minutes. The precipitate was filtered and air dried to give the 1st crop of product. The biphasic filtrate was separated, and the organic phase was washed with brine (300 ml), dried over anhydrous sodium sulfate, and concentrated. The residue was taken up in DCM (100 ml), stirred for 15 minutes, and filtered to give a 2nd crop of product. The combined yield of Cyclopropane-1,1-dicarboxylic acid (4-benzyloxy-3-fluoro-phenyl)-amide(4-fluoro-phenyl)-amide 64.5 g, yield: 98%. 1H-NMR (300MHz, CDCl3) delta: 8.9 (m, 2H), 7.35-7.18 (m, 8H), 6.95-6.85 (m, 4H), 5.03 (s,2H), 1.53(s, 2H).

According to the analysis of related databases, 168268-00-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Li, Jieming; Gu, Weijie; Bi, Xinzhou; Li, Huilan; Liao, Chen; Liu, Chunxia; Huang, Wenlong; Qian, Hai; Bioorganic and Medicinal Chemistry; vol. 25; 24; (2017); p. 6674 – 6679;,
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Reference of 14869-41-1, These common heterocyclic compound, 14869-41-1, name is 2-(2-Chloroethoxy)acetic acid, 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.

In a glass RBF equipped with a Teflon-coated magnetic stirrer was dissolved 4-fluoro-2-methoxy-5- nitro-phenylamine (1 eq.) in DMF (0.32 M). To this was then added sequentially HATU (1.2 eq.), DMAP (0.1 eq.), (2-chloro-ethoxy)-acetic acid (1.1 eq.) and finally ethyl-diisopropylamine (3 eq.). When the reaction was deemed to be complete by LCMS (14 h), the reaction mixture was diluted with EtOAc and washed sequentially with 10percent aq. HC1, sat. aq. NaHCO3, water and brine. The organic extract was then dried over MgSO4 and filtered. Concentration of the filtrate thus obtained in vacuo furnished the desired product as a tan solid (99percent yield).

The synthetic route of 14869-41-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK PATENT GMBH; JORAND-LEBRUN, Catherine; LAN, Ruoxi; CHEN, Austin; CLARK, Ryan C.; (268 pag.)WO2017/49068; (2017); A1;,
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Related Products of 2734-70-5, The chemical industry reduces the impact on the environment during synthesis 2734-70-5, name is 2,6-Dimethoxyaniline, I believe this compound will play a more active role in future production and life.

To an ice-cooled solution of 2,6-dimethoxyaniline (Amfinecom Inc., 1.2 g, 7.8 mmol) in DCM (20 mL) was added N,N-diisopropylethylamine (2.73 mL, 15.7 mmol) via syringe followed by a solution of 1,3-thiazole-2-carbonyl chloride (Maybridge, 1.16 g, 7.9 mmol) in DCM (27 mL) slowly via cannula. The resulting brown solution was allowed to warm to RTand stirred for 19 h. The reaction was then partitioned between water (80 mL) and DCM (2X). The combined organic layers were washed with brine (2X), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (eluent: 10-100percent EtOAc in hexanes) to provide 396.1 (1.30 g, 63percent yield) as a light yellow solid. LCMS-ESI (pos.) m/z: 265.2 (M+H)+.

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, 2,6-Dimethoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AMGEN INC.; CHEN, Ning; CHEN, Xiaoqi; CHEN, Yinhong; CHENG, Alan C.; CONNORS, Richard V.; DEIGNAN, Jeffrey; DRANSFIELD, Paul John; DU, Xiaohui; FU, Zice; HARVEY, James S.; HEATH, Julie Anne; HEUMANN, Lars V.; HORNE, Daniel B.; HOUZE, Jonathan; KALLER, Matthew R.; KAYSER, Frank; KHAKOO, Aarif Yusuf; KOPECKY, David J.; LAI, Su-Jen; MA, Zhihua; MEDINA, Julio C.; MIHALIC, Jeffrey T.; NISHIMURA, Nobuko; OLSON, Steven H.; PATTAROPONG, Vatee; SWAMINATH, Gayathri; WANG, Xiaodong; WANSKA, Malgorzata; YANG, Kevin; YEH, Wen-Chen; (700 pag.)WO2018/97945; (2018); A1;,
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