Tag: M.W=200-300

Reference of 148547-19-7, These common heterocyclic compound, 148547-19-7, name is Methyl 4-bromo-3-methylbenzoate, 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.

Methyl-4-bromo-3-methylbenzoate (2.06g, 9mmol) and 4-Methoxycarbonyphenylboronic acid (1.62g, 9mmol) were added to a round-bottom flask and pumped into a glove box. Dry DMF (40mL) was added along with Pd(PPh3)4 (312mg, 0.27mmol) and cesium carbonate (4.40g, 13.5mmol). The flask was fitted with a septa, placed in an oil bath at 80C, and stirred overnight. The flask was removed from the oil bath and allowed to cool to room temperature at which time water (20mL) and ethyl acetate (20mL) were added and a white precipitate was removed by vacuum filtration. The filtrate was washed with brine (3×50mL) and dried over sodium sulfate. The volatiles were removed in vacuo and the crude residue was purified by silica gel column chromatography using hexanes and ethyl acetate as eluent. The product 4 was isolated as a white solid (1.77g, 69%). The NMR spectra matched that of the known compound.

The synthetic route of 148547-19-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Schumacher, William T.; Mathews, Madeleine J.; Larson, Sean A.; Lemmon, Carl E.; Campbell, Karin A.; Crabb, Brendan T.; Chicoine, Brent J.-A.; Beauvais, Laurance G.; Perry, Marc C.; Polyhedron; vol. 114; (2016); p. 422 – 427;,
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Related Products of 176694-36-3, A common heterocyclic compound, 176694-36-3, name is Methyl 4-fluoro-3-(trifluoromethyl)benzoate, molecular formula is C9H6F4O2, 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) 4-Dimethylamino-3-trifluoromethyl-benzoic acid methyl ester (12a) To a stirred solution of 4,48 g (22.5 mmol) 4-Fluoro-3-trifluoromethyl-benzoic acid methyl ester (Rarechem) and 60.0 ml dimethylsulphoxid are added 2.23 g (27.0 mmol) dimethylamine hydrochloride and 6.54 g (47.3 mmol) potassium carbonate. The reaction mixture is stirred for 8h at 60C in an autoclave and is reduced with high vacuum rotation evaporator at 65C. The residue is diluted with dichloromethane, washed twice with water. The combined water phases are extracted with dichloromethane. The combined dichloromethane phases are washed with diluted sodium hydrogen carbonate solution, dried with sodium sulphate and concentrated. The oily crude is purified by column chromatography and the desired product 12a is obtained in 72 % yield (4,00 g, 16,2 mmol). MS-ESI: 248 (M+ +1, 100).

The synthetic route of 176694-36-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer Schering Pharma Aktiengesellschaft; EP1897885; (2008); 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. 583-02-8, name is Ethyl 4-(trifluoromethyl)benzoate, This compound has unique chemical properties. The synthetic route is as follows., Formula: C10H9F3O2

First access to the microchannel reactor15 minutes of nitrogen replacement system air,Under full nitrogen protection conditions,Cool down between -40 and -30 C and start adding110 g (0.5 mol, 99%)Ethyl p-trifluoromethylbenzoate and 500a mixture of milliliters of methyl tert-butyl ether,At the same time, 0.183 liters (0.55 mol, 3 mol/L) were added dropwise.Butyl lithium solution,The reaction solution all enters the low temperature collector to obtain the compound (III);Re-use the metering pump to compound (III) and 66.1 g(0.6 mol, 99%) methyl methanesulfonate remained inBetween -40 and -30 C,Drip through the microchannel reactor for 2 hours,Sampling analysis did not detect ethyl trifluoromethylbenzoate, and the reaction solution was slowly added dropwise in ice water between 0-5 C under nitrogen protection conditions.The solvent was removed by distillation under reduced pressure to give a yellow solid;Confirmed by nuclear magnetic resonance,Target productEthyl 2-methylsulfonyl-4-trifluoromethylbenzoateThe amount of 146.5 grams,97% content,The yield was 96%.

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 583-02-8.

Reference:
Patent; Papanna (Beijing) Technology Co., Ltd.; Xing Wenlong; Fu Renji; (7 pag.)CN109705005; (2019); A;,
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Application of 91-44-1, 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. 91-44-1, name is 7-(Diethylamino)-4-methyl-2H-chromen-2-one belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: In a typical reaction, a Schlenk tube charged with coumarins (0.5mmol), dialkyl phosphite (1.0mmol), NHC palladium complex, AgNO3 and solvent (2mL) was heated at 80C for 10h. The mixture was then cooled, filtered and the filtrate was evaporated. Purification of the residue by column chromatography (silica, petroleum ether/ethylacetate=2/1-1/4, v/v) produced the pure products, which were characterized by 1H NMR and 13C NMR. The analytical data of the products were shown in the Supporting Information.

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, 7-(Diethylamino)-4-methyl-2H-chromen-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Yang, Liangru; Zhang, Xinchi; Yuan, Jinwei; Xiao, Yongmei; Mao, Pu; Journal of Organometallic Chemistry; vol. 818; (2016); p. 179 – 184;,
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107317-58-8, name is Methyl 4-bromo-3-(trifluoromethyl)benzoate, belongs to esters-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. Product Details of 107317-58-8

To a DMF solution (20 mL) of 4-bromo-3-trifluoromethylbenzoic acid methyl ester (1.07 g), copper(I) iodide (720 mg) and fluorosulfonyldifluoroacetic acid methyl ester (4.78 mL) were added, and the mixture was stirred overnight at 90C. The reaction mixture was left to stand to cool to room temperature and filtered through a Celite pad. The filtrate was concentrated under reduced pressure. Saturated brine was added to the residue, followed by extraction thrice, each with ethyl acetate. The extracts were combined and washed with saturated brine, followed by drying over sodium sulfate anhydrate. Insoluble matter was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by flash column chromatography (Yamazen Hi-Flash column 2L), whereby a mixture (632 mg) of the title compound and raw materials were yielded.

The synthetic route of 107317-58-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Daiichi Sankyo Company, Limited; EP2017263; (2009); A1;,
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Application of 609-12-1, A common heterocyclic compound, 609-12-1, name is Ethyl 2-bromo-3-methylbutanoate, molecular formula is C7H13BrO2, 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 solution of 2-bromo-3-methyllpropanoic acid ethyl ester (0.418 g, 2 mmol) and 4-bromobenzylthiol (0.402 g, 2 mmol) in DMF (5 mL) was cooled to 0 C and treated with K2CO3 (0. 414 G, 3. mmol). After stirring for 2 h, the reaction was quenched with 5% HC1 (15 mL) and diluted with ethyl acetate (50 mL). After seperation, the aqueous layer extracted with ethyl acetate (3 x 15 mL). The combined organic layers were washed with sat. aq NACL, dried over MGS04 and concentrated. Purification by flash column chromatography (5% ethyl acetate in heptane) provided (4-bromophen-yl-4-methylsulfanyl)-3- methylbutanoic acid ethyl ester (660 MG, 90%) as white solid. 1H NMR (CDC13), 7.43 (d, J = 8 Hz, 2 H), 7.18 (d, J = 8 Hz, 2 H), 4.17 (q, J = 6 Hz, 2 H), 3.75 (s, 2 H), 2.85 (d, J = 9 Hz, 1 H), 2.04 (m, 1 H), 1.29 (t, J = 6 Hz, 3 H), 1.02 (d, J = 6 Hz, 3 H), 0.98 (d. J = 6 Hz, 3 H).

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; THE INSTITUTE OF PHARMACEUTICAL DISCOVERY, LLC; WO2004/99170; (2004); A2;,
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Some common heterocyclic compound, 7149-03-3, name is Ethyl 4-amino-3-bromobenzoate, molecular formula is C9H10BrNO2, 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: C9H10BrNO2

The title compound was prepared following the procedure described in step-3 of Intermediate-33 by using 2-chloro-4-(4,4,5,5-tetramethyl- 1,3 ,2-dioxaborolan-2-yl)benzonitrile (0.950 g,3.S8mmol), ethyl 4-amino-3-bromobenzoate (step-2 of Intermediate-33, 0.850 g, 3.51 mmol),Pd(dppCi2(O.145 g, 0J77 rnrnoi), diglyme (10 mL), K2C03 (0.728 g, 5.27 mmol) to afford0.720 g of title product. ?H NMR (300 MHz, DMSO-d6): 8.04-8.01(d, J = 8.4Hz, 1H), 7.76(m, 2H), 7.57 (m, 2H), 6.80 (d, 1H), 5.96 (s, 2H), 4.22-4.20 (q, J = 6.9Hz, 2H), 1.28-1.23 (t, J = 6.9Hz, 3H):_To a solution of ethyl 4-amino-3-bromobenzoate (5.0 g, 20.66 mmol), (4- cyanophenyl)boronic acid (3.33 g, 22.72 mmol) and Pd(dppf)C12 (0.843 g, 1.03 mmoi) indiglyme (10 mL) was added K2C03 (4.27 g, 30.99 mmol). The reaction mixture was heated at80C for 4 h. The reaction mass was quenched with water and extracted with EtOAc. The organic layer was washed with water and brine. The organic layer was separated, dried, filtered and concentrated to afford 2.7 g of title product. ?H NMR (300 MHz, DMSO-d6): 7.92-7.89 (d, J = 7.8 Hz, 2H), 7.69-7.67 (d, J = 8.7 Hz, 1H), 7.63-7.60 (d, J = 7.8 Hz, 2H),7.56 (s, 1H), 6.8 1-6.78 (d, J = 8.4Hz, 1H), 5.83 (br s, 2H), 4.22-4.20 (q, J = 6.9 Hz, 2H),1.28-1.23 (t, J= 7.5 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7149-03-3, its application will become more common.

Reference:
Patent; GLENMARK PHARMACEUTICALS S.A.; GHARAT, Laxmikant Atmaram; MUTHUKAMAN, Nagarajan; PISAL, Dnyandeo; KHAIRATKAR-JOSHI, Neelima; SHAH, Daisy Manish; KADAM, Sheetal R; (303 pag.)WO2016/55947; (2016); A1;,
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28170-07-2, name is Benzyl phenyl carbonate, belongs to esters-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. Safety of Benzyl phenyl carbonate

A mixture of 1,6-diaminohexane 39 (39.15 g, 0.338 mol) and benzyl phenyl carbonate (35.7 g, 0.156 mol) inethanol (125 ml) was stirred for 2 hours at room temperature and subsequently heated for an additional hour atreflux to achieve full conversion. The reaction mixture was allowed to cool to room temperature, affording awhite precipitate. After removing the precipitate by filtration, the supernatant was evaporated to dryness anddissolved in 330 ml 2 M aqueous HCl. The resulting solution was extracted with dichloromethane (DCM)(2×150 ml). The aqueous phase was subsequently adjusted to pH = 10 with 6 M aqueous NaOH and extractedwith DCM (3×150 ml). All organic phases were combined, dried over Na2SO4, evaporated to dryness, anddissolved in 200 ml diethyl ether. The resulting solution was extracted with 1M aqueous NaOH (3×50 ml), driedover Na2SO4, and evaporated to dryness to afford crude 40. The product was recrystallized from diethyl ether at-18C to afford white crystals (12.0 g, 31 %). 1H NMR (400 MHz, CDCl3): delta 1.03 (br.s, 2H), 1.58-1.14 (m, 8H),2.66 (t, J = 6.9 Hz, 2H), 3.18 (q, J = 6.7 Hz, 2H), 4.83 (br.s, 1H), 5.08 (s, 2H), 7.45 – 7.19 (m, 5H) ppm. 13CNMR (400 MHz, CDCl3): delta 26.63, 26.68, 30.07, 33.83, 41.12, 42.25, 66.67, 128.17, 128.21, 128.61, 136.78,156.51 ppm. RP-LCMS: calc. Mw= 250.2 g/mol, found m/z: 251.3 [M+H]+.Synthesis of

The synthetic route of 28170-07-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; De Feijter, Isja; Goor, Olga J. G. M.; Hendrikse, Simone I. S.; Comellas-Aragones, Marta; Soentjens, Serge H. M.; Zaccaria, Sabrina; Fransen, Peter P. K. H.; Peeters, Joris W.; Milroy, Lech-Gustav; Dankers, Patricia Y. W.; Synlett; vol. 26; 19; (2015); p. 2707 – 2713;,
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Electric Literature of 2967-66-0, The chemical industry reduces the impact on the environment during synthesis 2967-66-0, name is Methyl 4-(trifluoromethyl)benzoate, I believe this compound will play a more active role in future production and life.

General procedure: Each substituted benzoic acid (1) (0.02 mol) was refluxed for 4 h in 20.0 mL (0.49 mol) of anhydrous methanol and 0.5 mL (0.01 mol) of sulphuric acid. The reaction mixture was cooled down to room temperature and the hydrazine hydrate 80% (v/v) (10.0 mL, 0.13 mol) was added. The system was maintained by vigorously stirring for more 30 min in reflux. In the case of compound with 4-nitro substituent group attached to the benzene moiety, after the addition of hydrazine hydrate 80% (v/v) at room temperature, the reaction mixture was cooled down in ice bath and maintained into stirring during 1 h. After this period, the mixture was maintained at low temperature to give 2.19,22

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, Methyl 4-(trifluoromethyl)benzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Palace-Berl, Fanny; Jorge, Saloma?o Do?ria; Pasqualoto, Kerly Fernanda Mesquita; Ferreira, Adilson Kleber; Maria, Durvanei Augusto; Zorzi, Rodrigo Rocha; De Sa? Bortolozzo, Leandro; Lindoso, Jose? A?ngelo Lauletta; Tavares, Leoberto Costa; Bioorganic and Medicinal Chemistry; vol. 21; 17; (2013); p. 5395 – 5406;,
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Electric Literature of 40876-98-0,Some common heterocyclic compound, 40876-98-0, name is Sodium 1,4-diethoxy-1,4-dioxobut-2-en-2-olate, molecular formula is C8H11NaO5, 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 mixture of0.01 mol of diethyl oxalylacetate sodium salt, 0.01 molof aromatic aldehyde, and 0.01 mol of urea was heatedat reflux in 10 mL of acetic acid for 2 h. The mixturewas kept for 24 h at room temperature, the precipitatewas filtered off and recrystallized from ethanol.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Sodium 1,4-diethoxy-1,4-dioxobut-2-en-2-olate, its application will become more common.

Reference:
Article; Gein; Zamaraeva; Volkova; Dmitriev; Russian Journal of Organic Chemistry; vol. 52; 5; (2016); p. 730 – 733; Zh. Org. Khim.; vol. 52; 5; (2016); p. 740 – 743,4;,
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