Tag: M.W=200-300

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. 849758-12-9, name is Methyl 4-bromo-3-fluorobenzoate, A new synthetic method of this compound is introduced below., Formula: C8H6BrFO2

(32d) methyl 4-acetyl-3-fluorobenzoate Cobalt (II) bromide (976 mg, 4.46 mmol) and zinc (4.96 g, 75.8 mmol) were suspended in acetonitrile (40 mL) and, under a nitrogen atmosphere, allyl chloride (1.10 mL, 13.4 mmol) and trifluoroacetic acid (0.205 mL, 2.68 mmol) were added, and the mixture was stirred for 10 min. A solution (60 mL) of methyl 4-bromo-3-fluorobenzoate (10.4 g, 44.6 mmol) produced in Example 32 (32c) and acetic anhydride (4.64 mL, 49.1 mmol) in acetonitrile was added, and the mixture was stirred at room temperature for 18 hr. To the reaction mixture was added 1.0 M hydrochloric acid (2.7 mL), and the mixture was extracted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate 10:1, V/V). The solvent of the object fraction was evaporated under reduced pressure to give the title object compound as a pale-yellow powder (1.78 g, yield 20%). 1H-NMR (CDCl3, 400 MH) delta: 2.68 (3H, d, J=4.6 Hz), 3.96 (3H, s), 7.77-7.95 (3H, m).

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; Kyoto Pharmaceutical Industries, Ltd.; SHIRAHASE, Hiroaki; TAKAHASHI, Kenji; SHOJI, Yoshimichi; TAKEDA, Shigemitsu; (111 pag.)US2016/207883; (2016); A1;,
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151583-29-8, name is Methyl 3-(3-bromophenyl)propanoate, 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. SDS of cas: 151583-29-8

General procedure: In distinct reactors, 3-(bromophenyl)-propionic methyl esters 16, 17 (1.0 equiv) were dissolved in toluene (7 mL). Phenyl boronic acids 18-21 (2 equiv) in EtOH (3.5 mL) and Na2CO3 2 M (2 M, aq, 3.0 equiv) were then added to the corresponding reactors, and the resulting mixtures were deoxygenated with a stream of N2. After 10 min, Pd(PPh3)4 (0.005 equiv) was added and each mixture was stirred at reflux temperature for 5 h under N2, then cooled to room temperature and treated as follows. Each solution was poured into a mixture of H2O (5 mL) and Et2O (5 mL), and the two phases were separated. The aqueous layer was washed with Et2O (5 mL), and the organic phases were combined and washed with 1 M NaOH (5 mL), followed by brine (5 mL), then dried over Na2SO4 and evaporated. Purification of each crude product performed by flash chromatography on silica gel (petroleum ether/EtOAc = 8/2) yielded the corresponding biphenyl propanoic acid methyl esters 22a-e (Scheme 3).

The synthetic route of 151583-29-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chiriano, Gianpaolo; De Simone, Angela; Mancini, Francesca; Perez, Daniel I.; Cavalli, Andrea; Bolognesi, Maria Laura; Legname, Giuseppe; Martinez, Ana; Andrisano, Vincenza; Carloni, Paolo; Roberti, Marinella; European Journal of Medicinal Chemistry; vol. 48; (2012); p. 206 – 213;,
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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. 57381-59-6, name is Methyl 5-bromo-2-fluorobenzoate, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H6BrFO2

Compound 3b (24.00 g, 102.99 mmol) was dissolved in methanol (300 mL), then N,N-dimethylformamide (100 mL), triethylamine (100 mL) was addedAnd [l,l-bis(diphenylphosphino)ferrocene]dichloropalladium (12.62 g, 15.45 mmol).Reaction solution at 80CAfter stirring for 16 hours under a carbon monoxide atmosphere (50 psi),The reaction solution was filtered, concentrated under reduced pressure, and extracted with ethyl acetate (500 mL×2). The organic phases were combined, dried, concentrated to dryness under reduced pressure and purified by silica gel column chromatography (petroleum ether/ethyl acetate=100-0%) to compound 3c (11.00 g).

The synthetic route of 57381-59-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhengda Tianqing Pharmaceutical Group Co., Ltd.; Nanjing Mingde Drug Discovery Co., Ltd.; Yao Yuanshan; Chen Bin; Chen Yuan; Li Ao; Xu Ran; Huang Zhensheng; Tian Dongdong; Li Hongwei; Yang Chengshuai; Li Jian; Chen Shuhui; (30 pag.)CN107954995; (2018); A;,
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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 51760-21-5 as follows. name: Dimethyl 5-bromoisophthalate

Example 23 Step a 2′-Trifluoromethyl-biphenyl-3.5-dicarboxylic acid dimethyl ester (23a”); An oven-dried vial containinga magnetic stir bar was charged with dimethyl-5-bromo isophthalate (500 mg, 1.83 mmol), Pd(OAc)2 (4 mg, 1.0 mol%), S-Phos (15.0 mg, 2.0 mol%), 2- (trifluoromethyl) -phenyl boronic acid (695 mg, 3.66 mmol, 2 equiv.) and powdered, anhydrous KsPO4(1.16 g, 5.49 mmol, 3 equiv.). The vial was capped with a Teflon septum and then evacuated and backfilled with azote (this sequence was repeated three times). Dry toluene (4.0 mL) was added through the septum via syringe and the resulting mixture was stirred at 100 0C for 24 h. The reaction mixture was then allowed to cool to room temperature, diluted with diethyl ether (20 mL), filtered through a thin pad of silica gel (eluting with EtOAc) and concentrated under reduced pressure. The golden oil obtained which solidified upon standing was used as such. LCMS m/z 356 (M+Na)+, Rf = 0.32 (EtOAc/n-Heptane, 1/1).

According to the analysis of related databases, 51760-21-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MEDIVIR AB; WO2008/119773; (2008); A1;,
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These common heterocyclic compound, 146307-51-9, name is trans-Methyl 4-((tert-butoxycarbonyl)amino)cyclohexanecarboxylate, 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. SDS of cas: 146307-51-9

Reference Example 2;: Trans-4-(2-oxopyrrolidin-1-yl)cyclohexanecarboxylic acid ; [] (1) Methyl trans-4-[(t-butoxycarbonyl)amino]-cyclohexanecarboxylate (234.0 g) obtained in Reference Example 1 is dissolved in dioxane (500 ml), and thereto is added 4 N hydrogen chloride/dioxane (500 ml), and the mixture is stirred at room temperature for 19 hours. The reaction solution is concentrated under reduced pressure, and the resulting residue is suspended in diethyl ether. The precipitates are collected by filtration to give methyl trans-4-aminocyclohexanecarboxylate hydrochloride (121.9 g). APCI-MS M/Z:158[M+H]+.;

The synthetic route of trans-Methyl 4-((tert-butoxycarbonyl)amino)cyclohexanecarboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TANABE SEIYAKU CO., LTD.; EP1582521; (2005); A1;,
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Electric Literature of 81474-46-6, These common heterocyclic compound, 81474-46-6, name is Methyl 4-bromo-7-methoxybenzo[d][1,3]dioxole-5-carboxylate, 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.

To a solution of 8 (14.4 g, 50.0 mmol) in THF (100.0 mL) at 0 C was added dropwise DIBALH (1.0 mol/L in hexane, 150.0 mL, 150.0 mmol). This mixture was stirred at 0 C for 30 min, then quenched by aq Rochelle salt (1 mol/L, 200 mL). It was evaporated in vacuo to remove the organic solvents, and water (100 mL) and CH2Cl2 (100 mL) was added to the residue. The organic layer was separated, and the water layer was extracted with CH2Cl2 (100 mL×2). The combined organic layer was washed with brine (150 mL×2), dried over anhydrous Na2SO4, filtered through a short silica gel pad and concentrated in vacuo to give 9 (13.0 g) as a white solid. Yield: 99%; mp 139-141 C; 1H NMR (300 MHz, CDCl3): delta 6.71 (s, 1H), 6.06 (s, 2H), 4.68 (d, 2H, J=6.24 Hz), 3.91 (s, 3H), 1.88 (t, 1H, J=6.24 Hz); 13C NMR (75 MHz, CDCl3): delta 147.0, 142.9, 135.0, 133.5, 108.4, 102.0, 93.3, 64.5, 56.7; IR (KBr) 3213, 2904, 1628, 1446, 1342, 1161, 1106, 1036, 699 cm-1; HRMS (ESI): calcd for C9H9BrO4Na [M+Na]+ 282.9576, found 282.9571.

The synthetic route of 81474-46-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ni, Jizhi; Xiao, Heping; Weng, Lipeng; Wei, Xiaofeng; Xu, Youjun; Tetrahedron; vol. 67; 29; (2011); p. 5162 – 5167;,
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These common heterocyclic compound, 206548-14-3, name is Methyl 2-amino-5-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. Formula: C9H10BrNO2

To a 100 mE round-bottom flask, 0.1 mol of 2-amino-3-methyl 5-bromobenzoic acid methyl ester having the structural formula ofVIII-2, 100 mE of ethanol, 0.3 mol of N,N-diethyl ethylenediamine were added, heated to 78 C. and reacted for 4 hours, afier treatment 27.5 grams of N-diethylaminoethyl-2-amino-3-methyl-5-bromobenzamide having a structural formula of III-2 was obtained, and the yield was 84.2%;

The synthetic route of Methyl 2-amino-5-bromo-3-methylbenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ZHAOQING ZHENGE BIOLOGICAL TECHNOLOGY CO., LTD; Wang, Boli; Zhao, Yong; He, Daohang; Li, Weiwen; US2015/322037; (2015); A1;,
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Reference of 3196-23-4, 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. 3196-23-4, name is Methyl 1-bromocyclohexanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A mixture of 2.5 g of zinc, 5.53 g (25 mmol) of bromo ester 1, a catalytic amount (5 mg) of HgCl2, and 40 mL of benzene was heated for 3 h under reflux. The mixture was cooled, 10 mmol of aldehyde 4a-4i was added, and the mixture was heated for 2 h under reflux.After cooling, the mixture was treated with 5% aqueous acetic acid, the organic phase was separated and dried over Na2SO4, and the solvent was distilled off.The crystalline product (7a-7i) was recrystallized from ethyl acetate. Treatment of the residue with methanol led to crystallization of compound 11a-11d which was recrystallized from methanol.

The chemical industry reduces the impact on the environment during synthesis Methyl 1-bromocyclohexanecarboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Article; Kirillov; Nikiforova; Vasyanin; Dmitriev; Russian Journal of Organic Chemistry; vol. 51; 4; (2015); p. 513 – 517; Zhurnal Organicheskoi Khimii; vol. 51; (2015); p. 530 – 534,5;,
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Electric Literature of 46064-79-3,Some common heterocyclic compound, 46064-79-3, name is Methyl 3-amino-4-bromobenzoate, molecular formula is C8H8BrNO2, 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 mixture of methyl 2-oxocyclooctanecarboxylate (32.0 g, 174 mmol), methyl 3-amino-4-bromobenzoate (20.0 g, 87 mmol) and ethanol (120 mL) was heated to reflux, at an oil bath of 130 C., acetic acid (1.5 mL) was added and the mixture was reflux for 1.5 hours. Hot PPA (200 g, 120 C.) was added to the reaction mixture carefully. The reaction mixture was heated at an oil bath of 130 C. for 3 hours. After cooling for a while, ice (200 g), ethyl acetate (60 mL) and petroleum ether (60 mL) were added to the reaction mixture, the mixture was concentrated until 200 mL solvent was removed. Then water (600 mL) and ethyl acetate (60 mL) were added, the resulting mixture was stayed at room temperature overnight. A light brown solid was slowly formed. The mixture was filtered and the filtered cake was dried to give a light brown solid, which was placed into methanol (90 mL). SOCl2 (30 mL) was added dropwise with cooling with an ice-bath. The resulting mixture was heated to reflux for 4 hours, concentrated and treated with saturated NaHCO3 solution (60 mL) and ethyl acetate (30 mL), filtered and the filtered cake was dried to give desired product (6.6 g) as a pale white solid (21%).

The synthetic route of 46064-79-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhou, Changyou; Ren, Bo; Wang, Hexiang; US2015/18356; (2015); A1;,
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Application of 756525-95-8, These common heterocyclic compound, 756525-95-8, name is tert-Butyl 9-Amino-4,7-dioxanonanoate, 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 mixture of compound 301 (8.16 g, 35.0 mmol, 1.0 eq. ) and saturated NaHCO3(40 mL) was cooled to 0 , to which compound 409 (5.43 g, 35.0 mmol, 1.0 eq. ) was added in portions. After stirring at 0 for 1 h, the reaction was warmed to r.t. and stirred for 1 h. The reaction was extracted with DCM (3 × 100 mL) and the organic extract was washed with brine, dried over anhydrous Na2SO4, concentrated and purified by SiO2column chromatography to give a white solid (6.76 g, 62%yield) . MS ESI m/z calcd for C15H23NO6[M+H]+314.15, found 314.15.

Statistics shows that tert-Butyl 9-Amino-4,7-dioxanonanoate is playing an increasingly important role. we look forward to future research findings about 756525-95-8.

Reference:
Patent; HANGZHOU DAC BIOTECH CO. LTD; ZHAO, Robert Yongxin; YANG, Qingliang; HUANG, Yuanyuan; ZHAO, Linyao; GAI, Shun; YE, Hangbo; LEI, Jun; XU, Yifang; CAO, Mingjun; GUO, Huihui; JIA, Junxiang; TONG, Qianqian; LI, Wenjun; ZHOU, Xiaomai; XIE, Hongsheng; BAI, Lu; CAI, Xiang; ZHUO, Xiaotao; ZHANG, Xiuzheng; ZHENG, Jun; (424 pag.)WO2019/127607; (2019); A1;,
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