Esters-buliding-blocks

Electric Literature of 1949-51-5, A common heterocyclic compound, 1949-51-5, name is Ethyl 3,5-diaminobenzoate, molecular formula is C9H12N2O2, 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.

In a round-bottom flask placed in an ice bath, 11 (1.0 eq.) was solubilized in a mixture of dioxane and water (2:1), followed by addition of triethylamine (Et3N; 2.2 eq.). Next, di-tert-butyl-dicarbonate ((Boc)2O; 1.0 eq.) was solubilized in a small amount of dioxane and added dropwise to the mixture. The reaction was stirred at room temperature overnight. The solvents were evaporated and the crude was dissolved in ethyl acetate and washed with 10% aqueous solution of citric acid and water. The collected organic phases were dried over MgSO4, concentrated in vacuo and purified by column chromatography (dichloromethane/acetonitrile 95/5-90/10). The desired product formed pale-yellow crystals (80% yield).

The synthetic route of 1949-51-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Czescik, Joanna; Zamolo, Susanna; Darbre, Tamis; Mancin, Fabrizio; Scrimin, Paolo; Molecules; vol. 24; 15; (2019);,
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Application of 3195-24-2,Some common heterocyclic compound, 3195-24-2, name is Diethyl 2,2-diallylmalonate, molecular formula is C13H20O4, 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 study of the RC of several substrates has also been carried out. Reactions were run in toluene at 80C in the presence of 1 to 5 mol% of cis-2, the higher catalyst loading being only necessary for the formation 17 featuring a tetra-substituted double bond (Table 4 below, entry 3). The RCM of unhindered malonate derivatives was achieved in short reaction times (less than 1 hour) and in good yields. Indeed, di- and tri-substituted cyclopentenes 15 and 9 were obtained in quantitative yields (entries 1 & 2). Nevertheless, highly constrained substrate 16 could not be cyclized with full conversion, even after 24h at 80C, and was isolated in 70% yield (entry 3). Finally, 6- and 7-membered rings 19 and 21 were obtained in respectively 96 and 87% yield, and no increase in reaction time compared to 5-membered ring 15 (entries 4 & 5). Of note, a dilution to 0.05M was necessary to obtain 21 without observing parallel formation of polymers. We next attempted the RCM of cyano analogues 24 and 26 (entries 6 & 7). Non-hindered cyclopentene 23 was isolated in good yield (88%), indicating that the presence of potentially chelating cyano groups was not detrimental to catalysis. Nevertheless, cis-2 was unable to promote the formation of 25, the starting material remaining unreacted. Tosylamine-based olefins were next investigated. The cyclization of these compounds was found very efficient regardless of hindrance and ring size. Indeed, 5-, 6- and 7-membered compounds 7, 27 and 29 were isolated in excellent yields (entries 8-10), albeit a slight increase in reaction time was needed for larger rings. Catalyst loading of only 2 mol% was necessary to achieve the cyclizations of 30 and 32 to obtain tetrasubstituted 5- and 6-membered rings 31 and 33 in good yields (entries 11 & 12), even so 5 hours of reaction were needed for dihydropyrrole 31. Amide and ether-based substrates were also efficiently cyclized, with yields spanning from 80% to 99% (entries 13-17). Increasing the ring size to 6 or 7 members was not detrimental, as products 39, 41 and 43 were obtained excellent yields in less than 1 hour (entries 15-17). From this study, catalyst c/s-2 seemed to be highly tolerant to functionalities and able to effect RCM easily.This utility of the complexes of the invention is illustrated further in figure 4 which shows RCM of compound 30 (table 4 entry 11 ) in toluene at 80C carried out with a range of Ru complexes. Trans or cis-2 both rapidly produce a high conversion whereas prior art complexes Hov-ll, G-ll, M2 (structures shown in Scheme 1 ) and M31 (which is the pyridine complex 1 in scheme 2) did not produce any better than about 60% conversion (complex M2) under these conditions

The synthetic route of 3195-24-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY COURT OF THE UNIVERSITY OF ST ANDREWS; CAZIN, Catherine; WO2011/117571; (2011); 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 1070-64-0 as follows. Formula: C10H18Cl2O2

To a solution of ethyl 6,8-dichlorooctanoate (6.01 g, 25 mmol) in 95% ethanol (10mL)was added sodium hydroxide (2 g, 50 mmol) and water (38 mL). The mixture was heated to 50 C for 1.5 h and the aqueous disodium diselenide (prepared from 3.95 g selenium powder19) was then added dropwise at 65 C. After stirring for 2 h, the mixture was cooled to 40 C and activated carbon (8 g) was then added. After stirring for 0.5 h, the mixture was filtered, and the ethanol was distilled off under reduced pressure (caution: the temperatureof the filtrate must not exceed 50C). Water (400 mL) was added to the residue and the mixture was cooled to 0 C. A solution of 10% hydrochloric acid was then added dropwise till pH = 1, resulting in the formation of a solid product. The solid was filtered and washed thoroughly with water.

According to the analysis of related databases, 1070-64-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Xu, Feng; Yang, Zhen-Zhen; Zhang, Shi-Jie; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 188; 10; (2013); p. 1312 – 1319;,
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Application of 14062-29-4, The chemical industry reduces the impact on the environment during synthesis 14062-29-4, name is Ethyl 2-(3-chlorophenyl)acetate, I believe this compound will play a more active role in future production and life.

EXAMPLE 23 6-(3-Chlorobenzyl)-1-(2-methoxyphenyl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one In analogy to the preparation of Example 9, 180 mg (76% of theory) of the desired product are obtained as a colourless solid starting from 0.15 g (0.65 mmol) of 5-amino-1-(2-methoxyphenyl)-1H-pyrazole-4-carboxamide (Example 31A), 0.394 g (98% purity, 1.94 mmol) of ethyl (3-chlorophenyl)acetate and 0.129 g (3.23 mmol) of 60% sodium hydride. m.p.: 196 C. MS (ESI pos): m/z=367 (M+H)+ 1H-NMR (300 MHz, DMSO-d6): delta=3.7 (s, 3H), 3.9 (s, 2H), 7.0-7.6 (m, 8H), 8.2 (s, 1H), 12.4 (s, 1H) ppm.

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, Ethyl 2-(3-chlorophenyl)acetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bayer HealthCare AG; US2007/161662; (2007); A1;,
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Synthetic Route of 2969-81-5, 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. 2969-81-5, name is Ethyl 4-bromobutyrate, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 4-chlorophenol (10 g, 77.784 mmol, 1 equiv) in N,N- dimethylformamide (100 mL) was added anhydrous potassium carbonate (21 .5 g, 1 16.6 mmol, 2 equiv) and ethyl 4-bromobutanoate (16.7 mL, 1 16.677 mmol, 1 .5 equiv). The reaction mixture was heated to 140 C and stirred for 4 h. The progress of the reaction was monitored by TLC. After completion of reaction, the reaction mixture was allowed to cool to 27 C, filtered the solid and washed with ethyl acetate (700 mL). The filtrate was washed with water (2 x 200 mL), brine solution (100 mL), dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography using 10 % ethyl acetate in hexane as eluent to obtain ethyl 4-(4-chlorophenoxy)butanoate (17.0 g, 89 % yield) as white solid. LCMS (ES) m/z = 243.1 [M+H]+. NMR (400 MHz, CDCI3): delta ppm 1 .25 (t, J = 7.2 Hz, 3 H), 2.06 – 2.12 (m, 2 H), 2.49 (t, J = 7.6 Hz, 2 H), 3.97 (t, J = 6.0 Hz, 2 H), 4.1 1 – 4.17 (m, 2 H), 6.80 (d, J = 8.8 Hz, 2 H), 7.21 (d, J = 8.8 Hz, 2 H).

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

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; AXTEN, Jeffrey; CHEUNG, Mui; DEAN, Anthony W.; DEMARTINO, Michael P.; EIDAM, Hilary Schenck; KETHIRI, Raghava Reddy; KALITA, Biswajil; KRISTAM, Rajendra; (162 pag.)WO2017/212423; (2017); A1;,
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Electric Literature of 3044-06-2,Some common heterocyclic compound, 3044-06-2, name is Diethyl 2-(1-ethoxyethylidene)malonate, molecular formula is C11H18O5, 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: Diethyl ethoxymethylenemalonate (4.6mmol) were add to a solution of sodium hydride (9.7mmol) and compound 14a-l (4.2mmol) in ethanol (20mL), the reaction mixture was stirred at 80C for 2h. After the reaction completed, the mixture was added 10mL 6M hydrochloric acid and stirred for 0.5h, then the precipitate was collected by filtration. The resulting residue was recrystallized from ethanol to yield ethyl 2-(4-alkoxyphenyl-3-cyano)-6-oxo-1,6-dihydropyrimidine-5-carboxylate(15a-l).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Diethyl 2-(1-ethoxyethylidene)malonate, its application will become more common.

Reference:
Article; Mao, Qing; Dai; Xu, Gaoyang; Su, Yu; Zhang, Bing; Liu, Dan; Wang, Shaojie; European Journal of Medicinal Chemistry; vol. 181; (2019);,
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Application of 681465-85-0, 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. 681465-85-0, name is Methyl 4-amino-3-isopropoxybenzoate, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: The aryl carboxylic acid monomer (6 mmol, comp. 4-6), Mukaiyama reagent (6 mmol) and Et3N (12 mmol) were dissolved in an anhydrous dichloromethane (100 mL). The solution was refluxed for 15 min. under N2. Then a solution of the corresponding arylamine (5 mmol, comp. 7-9) in an anhydrous dichloromethane (20 mL) was added to the reaction mixture and resulting solution was refluxed for 2 days. The solvent was evaporated under vacuum and the residue was subjected to the column of silica gel using the mixture of hexanes/ dichloromethane (2:3) as an eluent to give amide coupling products in moderate to good yields. Note: for the synthesis of 18, 2.5 eq. of corresponding aryl amine over 2-methoxyisophthalic acid was used.

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

Reference:
Article; Kulikov, Oleg V.; Incarvito, Christopher; Hamilton, Andrew D.; Tetrahedron Letters; vol. 52; 29; (2011); p. 3705 – 3709;,
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Synthetic Route of 685-88-1,Some common heterocyclic compound, 685-88-1, name is Diethyl fluoromalonate, molecular formula is C7H11FO4, 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.

6-Fluoroimidazo[1 ,2-a]pyridine-3-carboximidamide (Preparation 1 b, 2.0 g, 8.39 mmol,) was added portionwise to a stirred solution of sodium (0.46 g, 20.21 mmol) in methanol (35 mL) at 0 C. Diethyl 2-fluoromalonate (2.65 mL, 16.8 mmol) was then added and the reaction mixture was stirred from 0 C to room temperature overnight. The solvent was evaporated to dryness and the resulting crude was dissolved in water (90 mL). After stirring for 30 min, a 2N solution of hydrochloric acid was added until acid pH. The solid formed was filtered and dried to yield the title compound (0.95 g, 43%) as a brown solid that was used in the next synthetic step without further purification. LRMS (m/z): 265 (M+1 )+ 1H NMR delta (300 MHz, DMSO-d6): 7.6 (s, 1 H), 7.8 (s, 1 H), 8.7 (s, 1 H), 10.1 (s, 1 H), 12.6 (bs, 1 H).

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

Reference:
Patent; ALMIRALL, S.A.; BACH TANA, Jordi; PEREZ CRESPO, Daniel; LLERA SOLDEVILA, Oriol; ESTEVE TRIAS, Cristina; TABOADA MARTINEZ, Lorena; WO2015/91531; (2015); A1;,
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Reference of 1186-73-8, The chemical industry reduces the impact on the environment during synthesis 1186-73-8, name is Trimethyl methanetricarboxylate, I believe this compound will play a more active role in future production and life.

Step 5; methyl 9-chloro-l-(2,4-dimethoxybenzyl)-4-hydroxy-2-oxo-l,2,5,6- tetrahydrobenzo [2,3] oxepino [4,5-b] pyridine-3-carboxylate A solution of N-(8-chloro-3 ,4-dihydrobenzo [b] oxepin-5 (2H)-ylidene)- 1 -(2,4- dimethoxyphenyl)methanamine (4.4 g crude) and trimethyl methanetricarboxylate (4.9 g, 25.6 mmol) in Pl^O (13 mL) was heated at 230 C for 15 min. The reaction mixture was cooled to room temperature, and purified on silica gel using EtO Ac/Hex (0-60% gradient) to afford the product (2.6 g, 43%) as a yellow foam. XH NMR (500 MHz, CHCl3-i/) delta ppm 2.06 – 2.17 (m, 1 H) 3.18 (dd, J=15.09, 3.90 Hz, 1 H) 3.63 – 3.68 (m, 3 H) 3.75 – 3.79 (m, 3 H) 3.99 (s, 3 H) 4.37 (dd, J=9.81, 6.34 Hz, 1 H) 4.41 – 4.50 (m, 1 H) 4.93 – 5.04 (m, 1 H) 5.15 (d, J=15.76 Hz, 1 H) 6.32 – 6.44 (m, 2 H) 6.94 (d, J=8.35 Hz, 1 H) 7.06 – 7.12 (m, 2 H) 7.17 (s, 1 H) 13.80 (s, 1 H). LC-MS: 470.1 [M-H]”, RT 1.45 min.

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, Trimethyl methanetricarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PTC THERAPEUTICS, INC.; BRANSTROM, Arthur; JOSYULA, Vara Prasad, Venkata Nagendra; ARNOLD, Michael, Andrew; GERASYUTO, Aleksey, I.; KARP, Gary; WANG, Jiashi; WO2013/33228; (2013); A1;,
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Adding a certain compound to certain chemical reactions, such as: 59247-47-1, name is tert-Butyl 4-bromobenzoate, belongs to esters-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 59247-47-1, name: tert-Butyl 4-bromobenzoate

To a 50 mL round-bottom flask purged and maintained under an inert atmosphere of nitrogen was added (1S,4S,5R)-5-[[4-cyclopropyl-l-(2,6-dichlorophenyl)-1H-pyrazol-5- yl]methoxy]-2-azabicyclo [2.2.1] heptane li (200 mg, 0.53 mmol, 1.00 equiv.), toluene (5 mL), Pd(OAc)2 (25 mg, 0.11 mmol, 0.20 equiv.), Xantphos (64 mg, 0.11 mmol, 0.20 equiv), Cs2CO3 (518 mg, 1.59 mmol, 3.00 equiv.), and tert-butyl 4-bromo-2-fluorobenzoate (134 mg, 0.49 mmol, 1.10 equiv.). The resulting mixture was heated at 90¡ãC overnight and concentrated under vacuum. The residue was purified by silica gel column chromatography eluting with ethyl acetate/petroleum ether (1/3) to give tert-butyl 4-[(1S,4S,5R)-5-[[4-cyclopropyl-l-(2,6- dichlorophenyl)-1H-pyrazol-5-yl]methoxy]-2-azabicyclo[2.2.1] heptan-2-yl]-2-fluorobenzoate 2a (176 mg, 58percent) as a yellow solid

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, tert-Butyl 4-bromobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARDELYX, INC.; CHAO, Jianhua; (231 pag.)WO2019/55808; (2019); A1;,
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