Tag: M.W=100-200

Application of 1017779-69-9, A common heterocyclic compound, 1017779-69-9, name is 3-Fluoro-4-(trifluoromethoxy)aniline, molecular formula is C7H5F4NO, 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.

[0094] (a) In a 20 mL vial was added 3-fluoro-4-trifluoromethoxyaniline (150 mg, 0.769 mmol) in acetic acid (0.5 mL) at room temperature. Bromine (118 , 2.30 mmol, 3 eq.) was added and the reaction was stirred for several hours. Dichloromethane (2 mL) was added to break up the solidified reaction mixture, followed by more bromine (40 , 0.781 mmol, 1 eq.) addition. After stirring for another hour, dichloromethane was removed by gently blowing a stream of nitrogen to the reaction mixture. The solid was filtered and washed thoroughly with water and then dried under vacuum to give 2, 6-dibromo-3-fluoro-4- trifluoromethoxyaniline as a white solid (172 mg, 0.489 mmol, 64% yield).

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; CHEMOCENTRYX, INC.; DAIRAGHI, Daniel; DRAGOLI, Dean, R.; KALISIAK, Jarek; LANGE, Christopher, W.; LELETI, Manmohan, Reddy; LI, Yandong; LUI, Rebecca, M.; MALI, Venkat, Reddy; MALATHONG, Viengkham; POWERS, Jay, P.; TANAKA, Hiroko; TAN, Joanne; WALTERS, Matthew, J.; YANG, Ju; ZHANG, Penglie; WO2015/84842; (2015); A1;,
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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. 104-92-7, name is 1-Bromo-4-methoxybenzene, A new synthetic method of this compound is introduced below., Computed Properties of C7H7BrO

General procedure: In a nitrogen filled glove box, PdCl2(CH3CN)2 (3.25mg, 0.010025mmol) and 2a (11.8mg, 0.0375mmol) or 2b (17.7mg, 0.0375mmol) were measured into a 1 dram vial containing a small stir bar. The vial was sealed with a screw cap and septum and removed from the glovebox before adding Cy2NMe (235muL, 1.10mmol), aryl halide (1.00mmol), alkyl acetylene (1.10mmol), and 1:1 water/acetonitrile (2mL). The reaction vial was placed in a preheated oil bath at 80C and stirred until it reached completion as determined by gas chromatography (2-12h). Upon completion, the reaction mixture was taken into diethyl ether, washed with brine solution, dried with anhydrous magnesium sulfate, and filtered. The excess organic solvent was removed under reduced pressure, and the crude residues were taken into methylene chloride and evaporated onto silica gel under reduced pressure. Once dry, the silica gel mixture was used in column chromatography.

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; Moore, Jane N.; Laskay, Nicholas M.; Duque, Kevin S.; Kelley, Steven P.; Rogers, Robin D.; Shaughnessy, Kevin H.; Journal of Organometallic Chemistry; vol. 777; (2015); p. 16 – 24;,
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Synthetic Route of 64465-53-8, 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. 64465-53-8, name is 4-Fluoro-3-methoxyaniline, This compound has unique chemical properties. The synthetic route is as follows.

4-Fluoro-3-methoxyaniline (0.5 g, 3.55 mmol) in suspension in glacial acetic acid (15ml) is treated with a concentrated HCI (5 ml). The resulting solution is then cooled approximately to 0 0C and treated dropwise with a solution of sodium nitrite (0.245 g, 3.55 mmol) in water (2 ml). After 10 minutes the reaction mixture is added to a stirred solution of SO2/AcOH/CuCI2/H2O (40 ml) (the preparation of the reagent is described below). The reaction mixture is allowed to warm to room temperature and is stirred overnight. The reaction mixture is then poured into water (250 ml) and extracted with ethyl acetate (3 x 100 ml). The combined organic layers are washed with water (2 x 100 ml) followed by brine (100 ml) and dried over MgSO4. After filtration the solvent is removed in vacuo to give the titled product which is used crude in the next step.Preparation of the reagent SO2/AcOH/CuCI2/H2O:According to the reported procedure (E. E. Gilbert, Synthesis 1969, 1-10, p6), glacial acetic acid (100 ml), vigorously stirred at room temperature, is treated by bubbling SO2 gas. Once a saturated solution is achieved (approximately 10 g per 100 ml), the solution is treated with copper (II) chloride (4 g) in water (5 ml). The resulting mixture is allowed to settle to give a green solution.

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

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2007/68418; (2007); A1;,
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Reference of 2688-84-8,Some common heterocyclic compound, 2688-84-8, name is 2-Phenoxyaniline, molecular formula is C12H11NO, 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 solution of sodium nitrite (9.2 g, 0.135 mol) in water (20 ml) was added dropwise to a solution of 2-phenoxyaniline (25 g, 0.135 mol) in 40% hydrobromic acid (50 ml) at 0 C. and stirred for another 10 minutes. Then the reaction mixture was added to the boiling mixture of cuprous bromide (21.3 g, 0.149 mol) in 40% hydrobromic acid (50 ml) and after addition it was allowed to reflux for another 30 minutes. Reaction mixture was cooled, diluted with water and extracted with diethyl ether. The diethyl ether layer was washed with 5% hydrochloric acid, 10% potassium hydroxide, water, brine, dried over sodium sulfate and concentrated to give the crude intermediate. The sub.-title compound (14.8 g, 45%) was obtained by column purification of the crude intermediate using pet ether as eluent

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

Reference:
Patent; ASTRAZENECA AB; US2008/15237; (2008); A1;,
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These common heterocyclic compound, 1758-46-9, name is 2-Phenoxyethylamine, 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. Safety of 2-Phenoxyethylamine

General procedure: A 10mL microwave vial was charged with 4 or 5 or 6 (1.0 mmol), a small excess (1.2 mmol) of 2-phenoxy- or (2-methoxyphenoxy)-or (2,6-dimethoxyphenoxy)-ethanamine and a catalytic amount ofpotassium iodide in 1 mL of 2-methoxyethanol. The reaction wasstirred under microwave irradiation at 160 °C (pressure 100 PSI, power 50 W) for 30 min. Then the solvent was evaporated under reduced pressure. The residue was taken up with EtOAc, basified with 5percent NaOH. The organic layer was dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by flash column chromatography.

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

Reference:
Article; Franchini, Silvia; Manasieva, Leda Ivanova; Sorbi, Claudia; Battisti, Umberto M.; Fossa, Paola; Cichero, Elena; Denora, Nunzio; Iacobazzi, Rosa Maria; Cilia, Antonio; Pirona, Lorenza; Ronsisvalle, Simone; Arico, Giuseppina; Brasili, Livio; European Journal of Medicinal Chemistry; vol. 125; (2017); p. 435 – 452;,
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1515-81-7, name is 1-Methoxy-4-(methoxymethyl)benzene, 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. HPLC of Formula: C9H12O2

General procedure: A 25 mL Schlenk-type tube equipped with a magnetic stir bar was charged with o-substituted aniline 1a-1f. The reaction tube was evacuated and back-filled with O2. Under oxygen atmospheres, ethers or alcohols 2a-2n and DMSO were added at room temperature, then the reaction mixture was stirred at 120 C for 12 h. The reaction was monitored by TLC. After completion of the reaction, the resulting solution was cooled to room temperature, and neutralized with saturated NaHCO3 aqueous solution. The product was extracted with EtOAc or CHCl3, dried over anhydrous Na2SO4 and concentrated in vacuum. The crude product was purified by flash column chromatography on silica gel to give N-heterocyclic compounds 3.

The synthetic route of 1515-81-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chen, Xiuling; Qi, Hongxue; Wu, Shaofeng; Liu, Leng; Wen, Jianhui; Li, Wanxi; Guo, Fang; Bian, Yongjun; Li, Jun; Heterocycles; vol. 94; 1; (2017); p. 86 – 94;,
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Electric Literature of 6298-96-0, These common heterocyclic compound, 6298-96-0, name is 1-(4-Methoxyphenyl)ethylamine, 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 suspension of tert-butyl 4-(2-(6-methoxypyridin-3-yl)-2-oxoethyl)piperidine-1 -carboxylate (3.00 g, 8.97 mmol) and (S)-1 -(4-methoxyphenyl)ethan-1 -amine (2.00 mL, 13.5 mmol) in titanium(IV) isopropoxide (7.89 mL, 26.9 mmol) was stirred at 90 C. The reaction progress was monitored by LCMS (aliquots treated with MeOH, NaBH4, followed by 1 N HCI). LCMS indicated complete reaction after 1 hour. The yellow solution was cooled to 0 C, diluted with MeOH (15 mL), treated slowly with NaBH4 (0.509 g, 13.46 mmol) in portions. After 1 hour, the solution was warmed to RT and stirred for an additional 4 hours.. The reaction was quenched with saturated aqueous NH4CI and 1 N HCI and then extracted with EtOAc. The EtOAc solution was washed with saturated aqueous NaHC03, brine, dried over Na2S04, filtered, and concentrated. 1H-NMR analysis of the crude material showed an approximately 2:1 mixture of SS : RS diastereomers. Purification by flash chromatography (silica gel, 0-100% EtOAc/hexanes, gradient elution) afforded tert- butyl 4-((S)-2-(((S)-1 -(4-methoxyphenyl)ethyl)amino)-2-(6-methoxypyridin-3- yl)ethyl)piperidine-1 -carboxylate (2.39 g, 57% yield) as clear oil. LCMS (ESI) m/z calcd for C27H39N3O4: 469.3. Found: 470.4 (M+1)+. NMR (400MHz, CDCI3) delta 7.85 (s, 1H), 7.48 (d, J = 8.6 Hz, 1H), 7.12 (d, J = 8.2 Hz, 2H), 6.87 (d, J = 8.2 Hz, 2H), 6.76 (d, J = 8.6 Hz, 1H), 4.08 – 3.88 (m, 5H), 3.82 (s, 3H), 3.40 (q, J = 6.4 Hz, 1H), 3.33 (t, J = 6.6 Hz, 1H), 2.67 – 2.43 (m, 2H), 1.66 – 1.48 (m, 2H), 1.47 – 1.16 (m, 15H), 1.09 – 0.82 (m, 2H).

Statistics shows that 1-(4-Methoxyphenyl)ethylamine is playing an increasingly important role. we look forward to future research findings about 6298-96-0.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; EVINDAR, Ghotas; KAZMIERSKI, Wieslaw Mieczyslaw; MILLER, John Franklin; SAMANO, Vicente; SUWANDI, Lita; TEMELKOFF, David; WASHIO, Yoshiaki; XIA, Bing; (152 pag.)WO2019/3142; (2019); A1;,
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Some common heterocyclic compound, 39021-83-5, name is 1,4-Dimethoxy-2,3-dimethylbenzene, molecular formula is C10H14O2, 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: 1,4-Dimethoxy-2,3-dimethylbenzene

The compound 72 (5 g, 30.1 mmol) was dissolved in TFA (50 mL) and hexamine (4.7 g, 33.1 mmol) was added to the resulting solution. The reaction mixture was refluxed under dry conditions for 2 hours. The TFA was evaporated under reduced pressure and the residue was dissolved in EtOAc (100 mL) . and the The resulting organic solution was washed with water (3×50 mL) and then dried over Na2SO4. The solvent organic phase was evaporated concentrated in vacuum and the residue was subjected to silica gel column chromatography (petroleum ether/EtOAc 20: 1 to 10: 1) to giveproduct 73 (3.1 g, 53) as a white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 39021-83-5, its application will become more common.

Reference:
Patent; XW LABORATORIES, INC.; XW LABORATORIES INC.; XIANG, Jia-Ning; QI, Zude; NING, Dezheng; LIU, Xianbo; (152 pag.)WO2019/33330; (2019); A1;,
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Synthetic Route of 349-65-5, 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 349-65-5 as follows.

To a stirring solution of phosgene (1.9 M in toluene; 2.07 mL 0.21 g, 1.30 mmol) in CH2Cl2 (20 mL) at 0 C. was added anh pyridine (0.32 mL) followed by 2-methoxy-5-(trifluoromethyl)aniline (0.75 g). The yellow solution was allowed to warm to room temp during which a precipitate formed. The yellow mixture was stirred for 1 h, then concentrated under reduced pressure. The resulting solids were treated with anh toluene (20 mL) followed by 4-(2-(N-methylcarbamoyl)-4-pyridyloxy)aniline (prepared as described in Method A2; 0.30 g) and the resulting suspension was heated at 80 C. for 20 h, then allowed to cool to room temp. The resulting mixture was diluted with water (100 mL), then was made basic with a saturated NaHCO3 solution (2-3 mL). The basic solution was extracted with EtOAc (2×250 mL). The organic layers were separately washed with a saturated NaCl solution, combined, dried (MgSO4), and concentrated under reduced pressure. The resulting pink-brown residue was dissolved in MeOH and absorbed onto SiO2 (100 g). Column chromatography (300 g SiO2; gradient from 1% Et3N/33% EtOAc/66% hexane to 1% Et3N/99% EtOAc to 1% Et3N/20% MeOH/79% EtOAc) followed by concentration under reduced pressure at 45 C. gave a warm concentrated EtOAc solution, which was treated with hexane (10 mL) to slowly form crystals of N-(2-methoxy-5-(trifluoromethyl)phenyl)-N’-(4-(2-(N-methylcarbamoyl)-4-pyridyloxy)phenyl) urea (0.44 g): TLC (1% Et3N/99% EtOAc) Rf 0.40.

According to the analysis of related databases, 349-65-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER CORPORATION; US2003/207872; (2003); A1;,
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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. 54149-17-6, name is 1-Bromo-2-(2-methoxyethoxy)ethane, A new synthetic method of this compound is introduced below., Safety of 1-Bromo-2-(2-methoxyethoxy)ethane

Example 1: Synthesis of ironflID /wgyo-tetrakis(N.N-di-(2-(2-methoxyethoxy)ethv?- imidazol-2-vnporphyrin (6) ;(“FeTDPImP”)FeTDPImp (FW: 1626.2 g/mol) was synthesized from a starting imdizaole compound using the following synthetic scheme. The synthetic scheme is shown, along with structures of intermediate products, in FIGS. 2A and 2B.1. Synthesis of N-( 2-(2-methoxyethoxy)ethvI>imidazole (2)Imidazole Ig (0.015 mol) was dissolved in dry DMF 50 mL under argon atmosphere. After a NaH mineral oil dispersion (60%) 0.68g (0.017mol) was added, the mixture was heated at 80 0C for 70 min. After cooling to room temperature, l-Bromo-2- (2-methoxyethoxy)-ethane (1), 2.75 g (0.015 mol), was added, then stirred overnight. The reaction was poured into water, extracted by CHCb, washed by water, dried over Na?SCU, then dried (Rotavap) until an oily residue remained. The crude product was purified with silica gel flash column chromatography with an eluant of CHCh : CH3<_)H=20: 1. 1.69 g(70% yield) of the product (2) was obtained as a colorless oil. As an alternative to column chromatography, product (2) is purified by vacuum distillation

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; TRUSTEES OF PRINCETON; WO2008/45358; (2008); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem