Month: November 2020

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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These common heterocyclic compound, 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene, 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. 54314-84-0

To a solution of Lambda/-[4-(7-Hydroxy-6-methoxy-quinoIin-4-yloxy)-phenyl]-benzamide (0.12g, 0.32mmol) in DMF (3ml) was added potassium carbonate (0.11g, O.deltammol, 2.5eq) and benzyl 3- bromopropyl ether (64ul, 0.36mmol, 1.1 eq). The reaction wasstirred at room temperature for 48 hours. The DMF was removed under reduced pressure and ethyl acetate was added to the crude residue, washing with water. The ethyl acetate layer was dried over magnesium sulphate and evaporated under reduced pressure. The product was purified by column chromatography, eluting with ethyl acetate/heptane (2:1 ) to yield the title compound (0.15g, 90percent) as a yellow solid, m/z 535 [M+H]+.

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 54314-84-0.

Reference:
Patent; CHROMA THERAPEUTICS LTD; WO2006/117570; (2006); A1;,
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Some common heterocyclic compound, 454-90-0, name is 3-(Trifluoromethyl)anisole, molecular formula is C8H7F3O, 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. 454-90-0

1. Preparation of 2-Propylthio-3-(trifluoromethyl)-anisole A solution of 30 mL (milliliter) (208 mmol) (millimole) of 3-(trifluoromethyl)anisole in 500 mL of dry tetrahydrofuran was cooled to -70 C. under a nitrogen blanket and 100 mL (250 mmol) of 2.5M butyl lithium in hexane was added slowly with stirring and cooling. The reddish solution was stirred at -70 C. for 1 hour and then 42 mL (270 mmol) of dipropyl disulfide was added slowly with stirring and cooling. The resulting mixture was allowed to warm to ambient temperature over an 18-hour period. The mixture was quenched with 250 mL of saturated aqueous ammonium chloride. The organic phase was recovered, dried over magnesium sulfate, and concentrated by evaporation under reduced pressure. The yellow oil residue was fractionally distilled in a Vigreux column at 0.2 mm Hg (millimeters of mercury) (27 Pascals) to obtain 37 g (gram) (71 percent of theory) of a clear liquid product fraction boiling at 92 C.

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

Reference:
Patent; Dow AgroSciences LLC; US5858924; (1999); A;,
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1535-75-7, 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. 1535-75-7, name is 2-(Trifluoromethoxy)aniline, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Pd(OAc)2 (20 mg, 0.09 mmol), (+/-)-BINAP (55 mg, 0.09 mmol), and DMF (5 mL) were charged in a round-bottom flask flushed with argon. The flask was evacuated and backfilled with argon. The mixture was stirred under argon for 30 min and added to a mixture of 27 (345 mg, 0.9 mmol), 2-trifluoromethoxyaniline (0.184 mL, 1.35 mmol), and K2CO3 (1.24 g, 8.97 mmol) in DMF (10 mL). The resulting mixture was stirred at 80 C for 4 h under argon. After cooling to room temperature, the reaction mixture was filtered on a pad of celite. The solvent was evaporated, the crude solid was purified by flash chromatography on silica gel (eluant: DCM/EtOH 90/10) to afford 210 mg (54%) of 31 as white solid.

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:
Article; Caldarelli, Marina; Angiolini, Mauro; Disingrini, Teresa; Donati, Daniele; Guanci, Marco; Nuvoloni, Stefano; Posteri, Helena; Quartieri, Francesca; Silvagni, Marco; Colombo, Riccardo; Bioorganic and Medicinal Chemistry Letters; vol. 21; 15; (2011); p. 4507 – 4511;,
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The chemical industry reduces the impact on the environment during synthesis 402-52-8, name is 1-Methoxy-4-(trifluoromethyl)benzene, I believe this compound will play a more active role in future production and life. 402-52-8

To chloro sulfuric acid (15 mL) was added l-methoxy-4-trifluoromethyl- benzene (3.0 g, 17 mmol) portionwise at 0C. The mixture was stirred at room temperature overnight. The mixture was poured into ice. the aqueous layer was extracted with EtOAc (50 mL x3). The extracts were dried over Na2S04 and the solution was filtered through a pad of silica gel, dried in vacuum to afford 500 mg (yield: 11%) of 2-methoxy-5-trifluoromethyl- benzenesulfonyl chloride as white solid. [00183] 1H NMR (DMSO-d6): delta = 7.90 (1H, d), 7.67 (1H, dd), 7.18 (1H, d), 3.84 (3H, s).

The chemical industry reduces the impact on the environment during synthesis 402-52-8. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SANFORD-BURNHAM MEDICAL RESEARCH INSTITUTE; PINKERTON, Anthony, B.; DAHL, Russell; COSFORD, Nicholas, D.P.; MILLAN, Jose, Luis; WO2013/126608; (2013); A1;,
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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. 4344-55-2 name is 4-Butoxyaniline, 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. 4344-55-2

1-bromonaphthalene: 22.78 g (110 mmol) 4-butoxyaniline: 8.26 g, 50 mmol Pd2 (dba)3: 1.007 g, 1.1 mmol P(t-Bu)3: 0.89 g (8.9 g in 10% hexane solution), 4.4 mmol tBuONa: 14.8 g, 154 mmol To a three-necked flask equipped with a reflux condenser, 1-bromonaphthalene, 4-butoxyaniline, Pd2 (dba)3, P(t-Bu)3, t-BuONa and toluene (150 ml) are added and stirred at 80 C. until the 4-butoxyaniline disappears as shown by HPLC analysis. After the reaction is completed, the reaction mixture is passed through a column packed with 6 inches of neutral alumina, and 2 L of toluene eluent is collected. The solvent is removed on rotary evaporator. The residue is extracted with 250 ml of diethyl ether, and the organic layer is washed with 3¡Á200 ml of brine. The organic layer is dried over MgSO4 and concentrated on a rotary evaporator. The crude product is recrystallized from isopropanol. The final product is an off-white powder with a purity of 98.5% as determined by HPLC; the yield is 54%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Butoxyaniline, and friends who are interested can also refer to it.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; US2012/264977; (2012); A1;,
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