Month: July 2021

Electric Literature of 7270-63-5,Some common heterocyclic compound, 7270-63-5, name is 5-Diazo-2,2-dimethyl-1,3-dioxane-4,6-dione, molecular formula is C6H6N2O4, 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: To a solution of diazo compound 1 (0.5 mmol) and alkynes (1.1 mmol) in toluene (2 mL) was added rhodium(II) pivalate (0.01 mmol). The reaction mixture was stirred at 60C for 0.5-5 h. The solvent was evaporated in rotary evaporator under reduced pressure to give the residue. The residue was purified by flash column chromatography on silica gel to give the product. 4.2.10. 2,4-Bis(3-fluorophenyl)-6H-furo[2,3-b]pyran-6-one (5i). Reaction of 1 (85 mg, 0.5 mmol) and 1-ethynyl-3-fluorobenzene (132 mg, 1.1 mmol) under Rh2(OPiv)4 (6 mg, 0.01 mmol) afforded 5i (69 mg, 43%) as a solid: mp 128-130 C; 1H NMR (300 MHz, CDCl3) delta 7.39-7.37 (3H, m), 7.34-7.27 (3H, m), 7.20-7.18 (1H, m), 6.99-6.96 (1H, m), 6.84 (1H, s), 6.18 (1H, s); 13C NMR (75 MHz, CDCl3) delta 164.6, 161.4, 159.0, 158.9, 152.3, 147.4, 137.0, 136.9, 131.1, 130.7, 123.3, 119.3, 117.9, 115.4, 114.7, 110.7, 105.6, 101.6, 99.4; IR (KBr) 2928, 1761, 1715, 1588, 1437, 1240, 1181, 1076, 926, 784, 692 cm-1; HRMS m/z (M+) calcd for C19H10F2O3: 324.0598. Found: 324.0599.

The synthetic route of 7270-63-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Somai Magar, Krishna Bahadur; Lee, Yong Rok; Kim, Sung Hong; Tetrahedron; vol. 69; 44; (2013); p. 9294 – 9302;,
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Electric Literature of 4224-69-5, These common heterocyclic compound, 4224-69-5, name is Methyl 2-(bromomethyl)acrylate, 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.

The solution of aldehyde 8 (13.0 g, 25 mmol) in THF (80mL) was mixed with saturated solution of NH4Cl (100 mL)and Zn dust (1.6 g, 50 mmol) at the room temperature. Themixture was stirred and the methyl 2-(bromomethyl)acrylate (7.2 g, 40 mmol) was added inseveral portions. The mixture was stirred for 1 hour, diluted with diethyl ether (900 mL), washedby brine (2×150 mL) and dried over Na2SO4. The solvents were evaporated and the product waspurified by column chromatography (EtOAc:hexane 1:2) to obtain 9 (13.4 g, 87%) as a colorlessliquid, diastereomeric mixture (~0.43:0.54 labeled as A and B).

Statistics shows that Methyl 2-(bromomethyl)acrylate is playing an increasingly important role. we look forward to future research findings about 4224-69-5.

Reference:
Article; Baranov, Mikhail S.; Kaskova, Zinaida M.; Grit?enko, Roman; Postikova, Svetlana G.; Ivashkin, Pavel E.; Kislukhin, Alexander A.; Moskvin, Dmitrii I.; Mineev, Konstantin S.; Arseniev, Alexander S.; Labas, Yulii A.; Yampolsky, Ilia V.; Synlett; vol. 28; 5; (2017); p. 583 – 588;,
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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. 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate, A new synthetic method of this compound is introduced below., Computed Properties of C9H16O3

A 250-mE 3-necked round-bottom flask fitted with a magnetic stir bar and thermometer was charged with ethyl 4-hydroxycyclohexane-i -carboxylate (1.5 g, 8.71 mmol), tnethylamine (2.64 g, 26.09 mmol) and dichloromethane (50 mE). To the reaction was added methanesulfonyl chloride (1.49 g, 13.01 mmol) added dropwise with stirring at 00 C. The resulting solution was stirred for 2 h at 25° C. The resulting solution was diluted with water (20 mE) and the product was extracted with dichloromethane (3×20 mE). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. The residue was purified by column chromatography eluting with ethyl acetate/petroleum ether (1:5, v/v) to afford ethyl 4-(methane- sulfonyloxy) cyclohexane- 1 -carboxylate as a light yellow oil (1.2 g, 55percent). ECMS: (ESI) mlz 251 [M+H], 155 [M-OMs].

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; Forma Therapeutics, Inc.; Ioannidis, Stephanos; Talbot, Adam Charles; Follows, Bruce; Buckmelter, Alexandre Joseph; Wang, Minghua; Campbell, Ann-Marie; Schmidt, Darby Rye; Guerin, David Joseph; Caravella, Justin A.; Diebold, R. Bruce; Ericsson, Anna; Lancia, JR., David; (225 pag.)US2016/185785; (2016); 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 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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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. 40061-54-9, name is Ethyl 2-(2-chlorophenyl)acetate, A new synthetic method of this compound is introduced below., Quality Control of Ethyl 2-(2-chlorophenyl)acetate

o-Chlorotoluene (1.89 g), ethanol (46 mg), di-tert-butyl peroxide (73 mg, 1 equivalent), and Pd(Xantphos)Cl2 (3.8 mg, 1 mol percent) were added into a reaction kettle, into which 10 atm carbon monoxide was introduced. The reaction was heated to 120° C., and stirred at this constant temperature for 16 h. After the reaction was completed, carbon monoxide was discharged, and 82 mg ethyl o-chlorophenylacetate was obtained by column chromatography, in a yield of 83percent. 1HNMR (400 MHz, CDCl3) delta 1.24 (t, J=7.2 Hz, 3H), 3.77 (s, 2H), 4.15 (q, J=7.2 Hz, 2H), 7.21-7.24 (m, 2H), 7.28-7.30 (m, 1H), 7.36-7.40 (m, 1H); 13CNMR (100 MHz, CDCl3) delta 14.2, 39.2, 61.0, 126.9, 128.6, 129.5, 131.4, 132.6, 134.6, 170.6; HRMS (ESI) calcd. for C10H11ClNaO2 [M+Na]: 221.0340. found: 221.0343. The ethyl o-chlorophenylacetate obtained was dissolved in 1,4-dioxane. 6 N sodium hydroxide solution was added, and the reaction was heated to 60° C. After 2 h of reaction, the pH value was adjusted to 1 by adding 2 N hydrochloric acid. After removing the organic solvent under reduced pressure, 66 mg product o-chlorophenylacetic acid was obtained by extraction with ethyl acetate, and the yield of hydrolysis was 94percent.

The synthetic route of 40061-54-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences; Huang, Hanmin; Xia, Chungu; Xie, Pan; US2013/303798; (2013); A1;,
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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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Adding a certain compound to certain chemical reactions, such as: 5445-17-0, name is Methyl 2-bromopropanoate, 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 5445-17-0, Safety of Methyl 2-bromopropanoate

tert-Butyl 5<;hloro-3-(1 -methoxycarbonylethyl)-2<>xo-2,3Patent; ABBOTT GMBH & CO. KG; WO2008/25736; (2008); 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. 13831-03-3, name is tert-Butyl propiolate, A new synthetic method of this compound is introduced below., Formula: C7H10O2

Lithium bis(trimethylsilyl)amide (4.95 mL, 4.95 mmol, 1.0 M in THF, 1.55 equiv.) was cooled to -78 C, then i-butyl propiolate (604 mg, 4.789 mmol, 1.5 equiv.) in 3 mL THF was added and the reaction mixture was stirred for 45 min. The solution was then added via cannula over 10 min to ketone (3R)-9 (953 mg, 3.193 mmol, 1 equiv.) in 5 mL THF at -78 C and stirred for 2 h. The reaction was quenched with satd aq NH4Cl (50 mL), warmed to rt, and extracted with EtOAc (4 x 50 mL). The combined organic extracts were dried (Na2SO4), filtered, and concentrated by rotary evaporation. Purification by silica flash chromatography (50%? 100% CH2Cl2 in hexanes) yielded the ester (15,3R)-10 as a clear viscous oil (1.05 g, 78%). IR (ATR): 3400, 2956, 2932, 2888, 2860, 2248, 1710, 1473, 1395, 1371, 1258, 1204, 1153, 1114, 1039, 1013, 909, 888, 838, 781, 751, 732, 695, 672, 657. 1H-NMR (500 MHz; CDCl3): delta 7.63-7.60 (m, 1H), 7.47-7.45 (m, 2H), 7.38-7.37 (m, 1H), 5.19 (dd, 7 = 8.0, 6.3 Hz, 1H), 2.96 (d, 7 = 2.3 Hz, 1H), 1.49 (s, 9H), 0.95 (s, 9H), 0.24 (s, 6H). 13C-NMR (126 MHz; CDCl3): delta 151.8, 139.5, 139.1, 130.9, 130.3, 124.9, 124.4, 124.2, 84.2, 80.6, 78.2, 74.9, 74.4, 28.0, 25.7, 18.2, -4.65, -4.84. 19F-NMR (471 MHz; CDCl3): delta delta -115.05 (d, 7 = 224.7 Hz, 1F), -128.46 (d, 7 = 224.6 Hz, 1F). HRMS (ESI) m/z calcd for C22H30O4F2SiNa ([M+Na]+) 441.1779; found 441.1785.

The synthetic route of 13831-03-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEMORIAL SLOAN-KETTERING CANCER CENTER; TAN, Derek, Shieh; EVANS, Christopher, E.; SHARMA, Indrajeet; TONGE, Peter, James; MATARLO, Joe, S.; (242 pag.)WO2017/59411; (2017); A1;,
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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. 63485-50-7, name is cis-Methyl 3-hydroxycyclobutanecarboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: 63485-50-7

Step 1: methyl (trans-3-(l,3-dioxo-2,3-dihydro-lH-isoindol-2-yI)cyclobutane-l- carboxylate : into a 250-mL round-bottom flask, under nitrogen, was placed a solution of methyl 3-cis-hydroxycyclobutane-l -carboxylate (8 g, 61.47 mmol, 1.00 equiv), 2,3-dihydro- l H-isoindole-l ,3-dione (18.1 g, 123.02 mmol, 2.00 equiv) and triphenylphosphine (32.3 g, 123.15 mmol, 2.00 equiv) in THF (100 mL). This was followed by the addition of D1AD (24.9 g, 123.14 mmol, 2.00 equiv) dropwise with stirring at 0 C. The resulting solution was stirred for 2.5 hours at room temperature. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1 :5). The crude product was re-crystallized from petroleum ether/ethyl acetate in the ratio of 10: 1. This resulted in 7.2 g (45%) of methyl trans-3-(l ,3-dioxo-2,3-dihydro-lH-isoindol-2- yl)cyclobutane-l -carboxylate as a white solid. LC-MS (ES, m/z): [M+l ]+ = 260. -NMR (400MHz, CDC13): delta 7.85-7.82 (m, 2H), 7.74-7.71 (m, 2H), 5.08-5.04 (m, 1 H), 3.75 (s, 3H), 3.34-3.32 (m, 1 H), 3.20-3.12 (m, 2H), 2.66-2.60 (m, 2H).

The synthetic route of 63485-50-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PROTEOSTASIS THERAPEUTICS, INC.; BASTOS, Cecilia, M.; MUNOZ, Benito; TAIT, Bradley; (96 pag.)WO2016/105468; (2016); A1;,
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