Author: Jessica.F

19056-40-7, 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. 19056-40-7, name is 4-Bromo-3-methoxyaniline, A new synthetic method of this compound is introduced below.

To a solution of 4-bromo-3-methoxyaniline (5.7 g, 28.2 mmol) in toluene (100 mL) and water (10 mL) were added tert-butyl 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan- 2-yl)-lH-pyrazole-l-carboxylate (9.96 g, 33.9 mmol), potassium phosphate (8.98 g, 42.3 mmol) and PdCl2(dppf)-DCM (1.152 g, 1.411 mmol) at RT. The reaction was stirred under argon at 95 ¡ãC for 2.5 hrs and then was cooled to RT. The reaction mixture was diluted with EtOAc, washed with H20, saturated aHC03 and brine. The organic phase was dried over sodium sulfate, filtered and concentrated. The crude product was purified by normal phase chromatography to give Intermediate 1 as light tan solid (5.1 g, 63percent yield). LCMS (ESI) m/z: 290.1 (M+H)+; XH NMR (400MHz, chloroform-d) delta 8.35 (d, J=0.5 Hz, 1H), 8.01 (s, 1H), 7.29 (d, J=8.0 Hz, 1H), 6.37 – 6.26 (m, 2H), 3.84 (s, 3H), 3.79 (br. s., 2H), 1.66 (s, 9H).

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; BRISTOL-MYERS SQUIBB COMPANY; HU, Zilun; QUAN, Mimi L.; WO2014/134391; (2014); A1;,
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136-90-3,Some common heterocyclic compound, 136-90-3, name is 4-Methoxy-3-methylphenylamine, molecular formula is C8H11NO, 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.

EXAMPLE 134 2-[N-(4-Methoxy-3-methylphenyl)-carbamyloxymethyl]-norborn-5-en-2-yl methyl ketone 2.1 g of 80% strength NaH suspension are added to a solution of 10.54 g (0.77 mole) of 4-methoxy-3-methylaniline in 30 ml of THF and the mixture is heated to 40 C. to complete the elimination of hydrogen. When this has ceased, a solution of 20.0 g (0.77 mole) of (2-acetylnorborn-5-en-2-yl)-methyl phenyl carbonate in 20 ml of tetrahydrofuran is added dropwise at room temperature, and the mixture is then stirred for 18 hours at 20 C. After having added a small amount of water, the solvent is stripped off and the residue is taken up in ether. The ether phase is washed repeatedly with 5% strength sodium hydroxide solution, and with water, and is dried over sodium sulfate. The crystalline crude product (11.8 g) is recrystallized from ethyl acetate; 6.4 g of 2-[N-(4-methoxy-3-methylphenyl)-carbamyloxymethyl]-norborn-5-en-2-yl methyl ketone, of melting point 121-122 C., are obtained. Analysis calc. 69.28% C, 7.04% H, 4.25% N, 19.4% O: found 69.4% C, 6.9% H, 4.3% N: C19 H23 NO4 M.Wt. =329.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 136-90-3, its application will become more common.

Reference:
Patent; BASF Aktiengesellschaft; US4335138; (1982); A;,
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2062-98-8, These common heterocyclic compound, 2062-98-8, name is Perfluoro(2-methyl-3-oxahexanoyl) fluoride, 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.

F[CF(CF3)CF2O]6CF(CF3)C(O)F, a precursor of hydrofluoroether F[CF(CF3)CF2O]7CH3, was formed by oligomerization of hexafluoropropylene oxide. To the reaction vessel, potassium fluoride (10.0 g), hexafluoropropylene oxide dimer (150.0 g) and tetraethylene glycol dimethyl ether (2.5 L) were added at 10 C under stirring.To the round bottom flask was introduced hexafluoropropylene oxide (830 g, 5.0 mol) over 1 hour.The lower acyl fluoride phase product is collected and consists mainly of hexafluoropropylene oxide oligomers. The crude product was further purified by distillation to obtain a product of a hexafluoropropylene oxide heptamer having a purity of 98% as determined by gas chromatography, and used in the next alkylation reaction. The structure of the product was characterized by infrared spectroscopy and 19F NMR.

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 2062-98-8.

Reference:
Patent; Tianjin Changlu Chemical New Materials Co., Ltd.; Yan Rui; He Guangrui; (15 pag.)CN109608312; (2019); A;,
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168971-68-4, The chemical industry reduces the impact on the environment during synthesis 168971-68-4, name is 1-Bromo-2-fluoro-4-(trifluoromethoxy)benzene, I believe this compound will play a more active role in future production and life.

Step 3: (1 -benzyl-3-(2-fluoro-4-(trifluoromethoxy)phenyl)-4-methyl-5-(trifluoromethyl)-1 H-pyrrol2-yl)(morpholino)methanone (SC-262)Under an nitrogen atmosphere (1 -benzyl-4-methyl-3-(4,4,5, 5-tetramethyl-l ,3,2-dioxaborolan-2-yl)-5- (trifluoromethyl)-IH-pyrrol-2-yl)(morpholino)methanone (50 mg, 0.106 mmol) was dissolved in DMF (0.5 mL) and LiOH (2 mg, 0.106 mmol), bis(tri-tert-butylphosphine)palladium (0) (3 mg, 0.007 mmol) and 1-bromo-2-fluoro-4-(trifluoromethoxy)benzene (24 mg, 0.096 mmol) were subsequently added. The reaction mixture was stirred at 80C under microwave irridation for I h. The mixture was cooled to RT and the reaction was stopped by addition of 1 M NaOH solution (2 mL). The crude product was extracted with EtOAc (2×3 mL) and the combined organic layers were washed with water (3×1 mL), dried over Na2SO4, filtered and the solvent was removed under reduced pressure. The crude mass was purified by flash chromatography to give SC-262 (34 mg, 66.8 %).

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-2-fluoro-4-(trifluoromethoxy)benzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; GRUeNENTHAL GMBH; SCHUNK, Stefan; REICH, Melanie; STEINHAGEN, Henning; DAMANN, Nils; SKONE, Philip; HAMLYN, Richard; KIRBY, Robert; ROGERS, Marc; SUTTON, Kathy; WO2014/32801; (2014); A1;,
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14869-41-1, name is 2-(2-Chloroethoxy)acetic acid, 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. 14869-41-1

27 mg, 0.34 mmol) of Intermediate 27a was added to 4 mL THF and stirred.Add 2-(2-chloro-ethoxy)acetic acid (48 mg, 0.34 mmol) and EEDQ (100 mg, 0.41 mmol), react at 60 ¡ã C for 4 hours, spin dry and add 5 mL of THF.NaH (40 mg, 1 mmol) was added portionwise with stirring, and reacted at room temperature for 5 hours.Add 0.2mL ammonium chloride solution, spin dry,The crude product was recrystallized from n-hexane andEtOAc to afford Intermediate 28z(174 mg, yield 76.0percent).

Statistics shows that 14869-41-1 is playing an increasingly important role. we look forward to future research findings about 2-(2-Chloroethoxy)acetic acid.

Reference:
Patent; Tianjin Pharmaceutical Institute Co., Ltd.; Wei Qunchao; Zheng Zhichao; Wang Songhui; Zheng Xuemin; Li Lingjun; Liu Lei; Yuan Jing; Zhang Shijun; Li Yuquan; Huang Changjiang; (38 pag.)CN109721539; (2019); A;,
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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. 29578-83-4 name is 1-Bromo-3-methoxy-5-methylbenzene, 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. 29578-83-4

Synthesis of 5-(1-(3-methoxy-5-methylphenyl)cyclohexyl)-2,2-dimethyl-1,3-dioxane-4,6-dione (3) A solution of 1-bromo-3-methoxy-5-methylbenzene (2, 8.0 g, 39.80 mmol) in tetrahydrofuran (20 mL) was added dropwise to a flask containing Mg turnings (1.36 g, 55.72 mmol) in tetrahydrofuran (30 mL). Catalytic iodine was added to the mixture and refluxed the reaction for 2 h. To a solution of 5-cyclohexylidene-2,2-dimethyl-1,3-dioxane-4,6-dione (1, 8.0 g, 35.71 mmol) in tetrahydrofuran (50 mL) at 0 C., freshly prepared (3-methoxy-5-methylphenyl)magnesium bromide was added slowly. The reaction was allowed to stir at room temperature for 12 h. On completion, the reaction mixture was quenched with 1 M hydrochloric acid and extracted with ethyl acetate (100 mL). The organic layer was washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated to afford 5-(1-(3-methoxy-5-methylphenyl)cyclohexyl)-2,2-dimethyl-1,3-dioxane-4,6-dione as a colorless liquid. Yield: 8.0 g, crude; MS (ESI) m/z 347.12 [M+1]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-3-methoxy-5-methylbenzene, and friends who are interested can also refer to it.

Reference:
Patent; eFFECTOR Therapeutics, Inc.; Sprengeler, Paul A.; Reich, Siegfried H.; Ernst, Justin T.; Webber, Stephen E.; Shaghafi, Mike; Murphy, Douglas; Tran, Chinh; (131 pag.)US10112955; (2018); B2;,
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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. 767-91-9 name is 2′-Methoxyphenyl acetylene, 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. 767-91-9

5b) 2-isopropoxy-5-(2-methoxy-phenylethynyl)-benzoic acid methyl ester 5-lodo-2-isopropoxy-benzoic acid methyl ester (500 mg), 2-methoxy-phenyl acetylene (0.40 ml), palladium dichlorobis(triphenylphosphine) (12 mg) and Cul (6 mg) in diethylamine (10 ml) were stirred at 60C for 12 hours. The reaction mixture was concentrated and extracted with ethylacetate / water. The combined organic layers were dried over sodium sulphate and the solvent was evaporated. The title compound was obtained in 64 % yield after flash chromatography. 1H-NMR (CDCl3): 7.97 d (J = 2.3 Hz, 1 H); 7.59 dd (J = 2.3 Hz / 8.7 Hz, 1 H); 7.47 dd (J = 7.5 Hz / 1.7 Hz, 1 H); 7.30 m (1 H); 6.96 m (3H); 4.62 m (1 H); 3.91 s (3H); 3.88 s (3H); 1.38 d (J = 8.7 Hz, 6H).

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

Reference:
Patent; Bayer Schering Pharma Aktiengesellschaft; EP1985612; (2008); 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. 6346-09-4, name is 4,4-Diethoxybutan-1-amine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 6346-09-4

Intermediate 145: 6-Chloro-N4-(4,4-diethoxybutyl>N2-methylpyridine-2,4- dicarboxamide (0902) (0903) To a solution of 2-chloro-6-(methylcarbamoyl)isonicotinic acid (2 g, 8.85 mmol) and HATU (3.70 g, 9.74 mmol) in DMF (20 mL) was added DIPEA (3.09 mL, 17.71 mmol) followed by 4,4- diethoxybutan-l-amine (1.68 mL, 9.74 mmol). The resulting solution was stirred at rt for 16 h. Water (60 mL) and EtOAc (60 mL) were added and the layers separated. The aqueous layer was further extracted with ethyl acetate (2 x 30 mL). The combined organics were back-extracted with water (2 x 30 mL) and sat. aqueous LiCI (30 mL) and then dried (Na2S04), filtered and concentrated in vacuo to give a dark oil. This was re-dissolved in DCM and directly applied to the top of a 100 g SNAP silica cartridge and purified by SP4 flash column chromatography. The column was eluted with a gradient of 30-70% ethyl acetate in cyclohexane. The appropriate fractions were collected and concentrated in vacuo to afford the product, 6-chloro-N4-(4,4-diethoxybutyl)-N2-methylpyridine-2,4-dicarboxamide (2.39 g, 6.68 mmol, 75 % yield) as a yellow oil. (0904) LCMS (2 min High pH): Rt = 0.92 min, [MH]- = 356.2.

The synthetic route of 6346-09-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; ATKINSON, Stephen John; DEMONT, Emmanuel Hubert; HARRISON, Lee Andrew; LEVERNIER, Etienne; PRESTON, Alexander G; SEAL, Jonathan Thomas; WALL, Ian David; WATSON, Robert J; WOOLVEN, James Michael; (225 pag.)WO2017/174621; (2017); 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. 946-80-5, name is Benzyl Phenyl Ether, This compound has unique chemical properties. The synthetic route is as follows., 946-80-5

A. 4-Benzyloxybenzenesulfonyl chloride To 0.87 g of dimethylformamide, at 0 C. under an atmosphere of nitrogen, was added 1.61 g of sulfuryl chloride. The mixture was stirred for 15 min and treated with 2.00 g of benzyl phenyl ether. The mixture was then heated at 100 C. for 1.5 h, cooled to about 40 C., poured onto ice, extracted with CH2 Cl2, dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by low pressure silica gel chromatography using 10% ethyl acetate in hexane as eluent to provide 0.78 g of the title product as a white solid. TLC: Rf=0.46, 10% ethyl acetate in hexane. (1 H)-NMR (CDCl3) consistent with structure.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Vertex Pharmaceuticals, Incorporated; US5783701; (1998); A;,
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A common compound: 1535-73-5, name is 3-Trifluoromethoxyaniline, belongs to ethers-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 1535-73-5

General procedure: A solution of cyanic bromide [Caution, highly toxic] (2 equiv) in diethyl ether (10 mL) was added dropwise to a solution of the appropriately substituted aniline (1 equiv) in diethyl ether (10 mL) at 0 ¡ãC. After complete addition the mixture was warmed to ambient temperature and stirred 1?20 h, which was followed by TLC. Solids were filtrated and washed with ether. The filtrate was washed with 1 M HCl (25 mL) followed by brine (25 mL). The organic layer was collected, dried over anhydrous MgSO4, filtrated and evaporated to dryness under reduced pressure. 5.1.33 N-(3-(Trifluoromethoxy)phenyl)cyanamide (24i) The reaction of 3-(trifluoromethoxy)aniline (23i) (1.780 g, 10.05 mmol) according to procedure A yielded, after purification over silica with ethyl acetate/petroleum ether (60-80) (25/75, v/v), the title compound as a white solid (583 mg, 2.88 mmol, 29percent); Rf 0.43 (ethyl acetate/petroleum ether (60-80), 25/75, v/v). 1H NMR (CDCl3) delta 7.39-7.32 (m, 2H, HAryl), 6.99-6.93 (m, 2H, HAryl), 6.88 (s, 1H, NH). 13C NMR (CDCl3) delta 150.34 (Ar-O), 139.03 (Ar-N), 131.15 (Ar), 120.47 (q, CF3, JCF = 258.08 Hz), 115.84 (Ar), 113.82 (Ar), 111.06 (NCN), 108.58 (Ar).

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, 1535-73-5, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Klein, Pieter J.; Christiaans, Johannes A.M.; Metaxas, Athanasios; Schuit, Robert C.; Lammertsma, Adriaan A.; Van Berckel, Bart N.M.; Windhorst, Albert D.; Bioorganic and Medicinal Chemistry; vol. 23; 5; (2015); p. 1189 – 1206;,
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