Tag: M.W=100-200

321-28-8, name is 1-Fluoro-2-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. Recommanded Product: 1-Fluoro-2-methoxybenzene

Step 1 Preparation of 3′-Fluoro-4′-methoxyacetophenone Aluminum chloride (80.0 g, 0.6 mol) and chloroform (750 mL) were placed in a 2 L three-necked round bottom flask fitted with a mechanical stirrer and cooled by means of an ice bath. To the stirred solution acetyl chloride (51.0 g, 0.65 mol) was added dropwise, maintaining the temperature between 5-10 C. The mixture was stirred for 10 minutes at 5 C. before the dropwise addition at 5-10 C. of 2-fluoroanisole (62.6 g, 0.5 mol). The mixture was stirred at 0-10 C. for 1 hour and poured into ice (1 L). The resultant layers were separated and the aqueous layer was extracted with dichloromethane (2*250 mL). The combined organic layers were washed with water (2*150 mL), dried over anhydrous MgSO4, filtered and concentrated in vacou to a volume of 300 mL. Hexanes were added and a white solid formed which was isolated by filtration and air dried. This material was recrystallized from a mixture of dichloromethane and hexanes to afford (77.2 g, 92%) of material suitable for use in the next step: mp 92-94 C.; 1 H NMR (D6 -DMSO) 7.8 (m, 2H), 7.3 (t, 1H), 3.9 (s, 3H), 2.5 (s, 3H).

The synthetic route of 321-28-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; G.D. Searle & Co.; US5521207; (1996); A;,
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Application of 74654-07-2,Some common heterocyclic compound, 74654-07-2, name is 2-(2-(2-Methoxyethoxy)ethoxy)ethanamine, molecular formula is C7H17NO3, 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 solution of 2 (1000 mg, 1.33 mmol), 1,3-dicyclohexylcarbodiimide (140 mg, 2.03 mmol), and allylamine (150 mg, 2.33 mmol) in 50 cm3 of dichloromethane and 1-hydroxybenzotriazole hydrate (225 mg, 1.46 mmol) dissolved in 15 cm3 of tetrahydrofuran were mixed together and stirred at 0 C for 1 h. After this time, the reaction mixture was stirred at room temperature for a further 24 h. Then the solvents were distilled under reduced pressure to dryness. The residue was suspended in hexane and filtered off to remove the 1,3-dicyclohexylurea by-product. The filtrate was evaporated under reduced pressure and purified by Dry Column Vacuum Chromatography on silica gel (Fluka type 60) to give 3a as a colourless solid (893 mg, 85% yield). Pure compound 3a was dissolved in acetonitrile. The solution was allowed to evaporate at room temperature. After several days the crystals were formed in 57% yield.

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-(2-Methoxyethoxy)ethoxy)ethanamine, its application will become more common.

Reference:
Article; Huczynski, Adam; Janczak, Jan; Stefanska, Joanna; Antoszczak, Michal; Brzezinski, Bogumil; Bioorganic and Medicinal Chemistry Letters; vol. 22; 14; (2012); p. 4697 – 4702;,
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Reference of 1978-39-8, These common heterocyclic compound, 1978-39-8, name is 5-Fluoro-2-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.

8-Fluoro-5-methoxy-2H-benzoreiri ,2,41thiadiazin-3(4H)-one 1 ,1 -dioxide (lnt-12) (2152) A 250 mL round-bottomed flask was charged with chlorosulfonyl isocyanate (2.058 ml) in nitropropane (20 ml) to give a colorless solution at -40 C under nitrogen. After 10 min, a solution of 5-fluoro-2-methoxyaniline (2.72 g) in nitropropane (10 ml) was added to the reaction mixture. After 10 min, the reaction was warmed to 0 C. After 1 h, aluminum chloride (3.21 g) was added to the reaction mixture. After 5 min, the reaction mixture was warmed to 1 10 C. After 30 min, the reaction mixture was poured in ice/water (400 mL) and stirred for 1 h. The solids were filtered and washed with water. The solids were placed in drying oven overnight at 50 C to obtain the titled compound (2.3 g). LCMS m/z 247.1 (M+H).

The synthetic route of 1978-39-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ADAMS, Jerry Leroy; ATOR, Laura E.; DUFFY, Kevin J.; GRAYBILL, Todd L.; KIESOW, Terence John; LIAN, Yiqian; MOORE, Michael Lee; RALPH, Jeffrey M.; RIDGERS, Lance Howard; (370 pag.)WO2017/98421; (2017); 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 768-70-7 as follows. Application In Synthesis of 3-Ethynylanisole

1.0 mmol of m-methoxyphenylacetylene, 1.5 mol of sodium azide, 1.2 mmol of benzyl bromide, and 0.1 mmol of cuprous iodide were added to 4002.0 mL of polyethylene glycol, and the reaction was stirred at room temperature for 35 minutes, and the reaction was completed. The product was treated by column chromatography V petroleum ether: V ethyl acetate = 3: 1 to obtain 1-benzyl-4- (3-methoxy) phenyl1,2,3-triazole. The product was a white solid. Yield: 92%.

According to the analysis of related databases, 768-70-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Leshan Normal University; Zeng Hongyao; Xia Liewen; Wang Yinghong; (13 pag.)CN110498772; (2019); A;,
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Electric Literature of 363-47-3,Some common heterocyclic compound, 363-47-3, name is 3,5-Difluoro-4-methoxyaniline, molecular formula is C7H7F2NO, 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: The relevant halogenated heterocycle (1.0equiv.), substituted aniline (2.0 equiv.) and TFA (5.0 equiv.) were takenup in TFE (0.1 M) and heated under microwave irradiation conditionsat 140 C for 30 min before being concentrated in vacuo. The residuewas resuspended in EtOAc:THF (1:1, 20 mL/mmol), washed with saturatedNaHCO3 solution (20 mL/mmol), and the aqueous phase wasfurther extracted with EtOAc:THF (1:1, 3 × 15 mL/mmol). The combinedorganic extracts were washed with brine, dried (MgSO4) andconcentrated in vacuo. The resultant residue was purified via columnchromatography and/or triturated as specified to afford the desired compound.

The synthetic route of 363-47-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Casalvieri, Kimberly A.; Matheson, Christopher J.; Backos, Donald S.; Reigan, Philip; Bioorganic and Medicinal Chemistry; vol. 28; 5; (2020);,
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Synthetic Route of 702-24-9,Some common heterocyclic compound, 702-24-9, name is 4-Methoxy-N-methylbenzylamine, molecular formula is C9H13NO, 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.

(4-Methoxyphenyl)-N-methylmethanamine (0.56 g, 3.75 mmol) and DBU (0.52 mL, 3.75 mmol) were added to a solution of Example A10 (0.98 g, 2.68 mmol) in NMP (10 mL) and the mixture was heated under Ar at 155° C. for 24 h. The mixture was cooled to RT, poured into water (50 mL) and extracted with EtOAc (2*). The combined organics were washed with brine, dried (Na2SO4), concentrated in vacuo and purified by chromatography (EtOAcDCM) to afford 7No.4-methoxybenzyl)(methyl)amino)-3-(5-amino-2-chloro-4-fluorophenyl)-1-isopropyl-1,6-naphthyridin-2(1H)-one (0.78 g, 60percent yield) as a white foam. MS (ESI) m/z: 481.0 (M+H+)

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

Reference:
Patent; Deciphera Pharmaceuticals, LLC; Flynn, Daniel L.; Kaufman, Michael D.; Petillo, Peter A.; US8461179; (2013); B1;,
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Reference of 41789-95-1,Some common heterocyclic compound, 41789-95-1, name is 1-(3-Methoxyphenyl)-N-methylmethanamine, molecular formula is C9H13NO, 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 solution of bromo heteroaryl carboxylic acid (2mmol), thionyl chloride (4mmol) and DMF (5 drops) in toluene (10mL) was refluxed at 110C for 4h. The reaction mixture was cooled to room temperature and the solvent and the excess of thionyl chloride removed under reduced pressure. To the residue was added at 0C the corresponding N-methyl amine (2mmol) and Et3N (2mmol) in CH2Cl2 (10mL) under N2 atmosphere. After 30min at 0C, the ice bath was removed and the solution was warmed up and stirred at room temperature overnight. The reaction mixture was extracted twice with CH2Cl2 (2×15mL) and the organic layer dried over MgSO4, filtered and the solution was concentrated under reduced pressure. The residue was purified by silica gel column chromatography using hexanes and EtOAc as eluant or by trituration in a mixture of diethyl ether/petroleum ether to afford the desired compound.

The synthetic route of 41789-95-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Perspicace, Enrico; Cozzoli, Liliana; Gargano, Emanuele M.; Hanke, Nina; Carotti, Angelo; Hartmann, Rolf W.; Marchais-Oberwinkler, Sandrine; European Journal of Medicinal Chemistry; vol. 83; (2014); p. 317 – 337;,
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Electric Literature of 1758-46-9, 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.

d) (8-Bromo-6-chloro-4-methyl-3,4-dihydro-quinazolin-2-yl)-(2-phenoxy-ethyl)-amine 8-Bromo-6-chloro-4-methyl-2-methylsulfanyl-3,4-dihydro-quinazoline hydroiodide (141 mg, 0.33 mmol) and 2-phenoxyethyl amine (53.5 mg, 0.39 mmol) were dissolved in acetonitrile (1 ml) and heated to 200° C. in a sealed tube in a microwave oven for 30 minutes. After cooling the reaction was treated with 1N aqueous sodium hydroxide solution, methylene chloride and 5 to 7 drops of 30percent aqueous hydrogen peroxide solution. After the reaction has ceased the layers were separated and the aqueous phase was extracted with methylene chloride. The combined organic layers were dried over sodium sulfate, filtered, the solvent was evaporated and the residue was purified by column chromatography (CH2Cl2:MeOH:aq conc NH3=9:1:0.1) to yield the title compound as an off-white solid (60 mg, 47percent). (MS: n/e=394.0, 396.0, 398.1 [M+H+]). 1H NMR (CDCl3): delta 1.22 (3H, d); 3.64 (2H, q), 4.12 (2H, t), 4.47 (2H, q), 6.25 (t, 1H), 6.50 (1H, s) 6.89-7.03 (4H, m), 7.25-7.31 (2H, m), 7.35 (1H, s).

The synthetic route of 1758-46-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Alanine, Alexander; Gobbi, Luca Claudio; Kolczewski, Sabine; Luebbers, Thomas; Peters, Jens-Uwe; Steward, Lucinda; US2006/252779; (2006); A1;,
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Synthetic Route of 592-55-2, A common heterocyclic compound, 592-55-2, name is 1-Bromo-2-ethoxyethane, molecular formula is C4H9BrO, 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.

Compound A2 (0.13 mmol, 50 mg), and 1-BROMO-2-ETHOXY-ETHANE (0.65 mmol, 99 mg) were dissolved in DMF (1 ML) and triethylamine (0.91 mmol, 127 GEL). The reaction was heated in a microwave at 80C for 20 minutes. The mixture was quenched with water and extracted with ethyl acetate. Removal of organic solvent in vacuo and purification by prep-TLC provided Compound A12 as a yellow solid (20 mg, 33%).’H NMR (400 MHz, CDC13) 8 (PPM) : 10.06 (s, 1H), 8.29 (s, 1H), 7.84 (d, 2H), 7.74 (d, 2H), 5.39 (s broad, 1H), 3.53 (M, 2H), 3.39 (q, 2H), 2.86 (s, 3H), 2.77 (M, 2H), 2.65 (M, 3H), 2.04 (M, 2H), 1.92 (m, 3H), 1.09 (M 3H). LCMS (ESI), m/z 466.3 (M+H+, 100%).

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; ARENA PHARMACEUTICALS, INC.; WO2005/7647; (2005); A1;,
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Application of 13101-88-7,Some common heterocyclic compound, 13101-88-7, name is 6-Methoxynaphthalen-2-amine, molecular formula is C11H11NO, 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.

28.2 g (0.16 mol) of the product synthesised in the previous step are dissolved in a mixture of dichloromethane/methanol: 1500/620 ml. To the resulting solution add, at ambient temperature, 56.7 g (0.16 mol) of benzyltrimethylammonium dichloroiodate and 21.2 g (0.212 mol) of calcium carbonate. After 30 minutes, filter off the insoluble material, then take up the organic phase with 10% sodium bisulphite solution and extract with ethyl ether. Dry over magnesium sulphate, filter and then evaporate. The residue is purified by chromatography over silica gel using a mixture of cyclohexane/ethyl acetate:70/30:v/v as eluant.

The synthetic route of 13101-88-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Lavielle, Gilbert; Muller, Olivier; Millan, Mark; Gobert, Alain; Di Cara, Benjamin; US2005/59675; (2005); A1;,
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