Category: esters-buliding-blocks

Application of 94994-25-9, A common heterocyclic compound, 94994-25-9, name is Methyl 4-formylbicyclo[2.2.2]octane-1-carboxylate, molecular formula is C11H16O3, 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 stirred solution of methyltriphenylphosphonium bromide (9.1 g, 12.8 mmol) in THF (50 ml) at 0 C. was added potassium hexamethyldisilazide (0.5M in toluene, 48.6 ml), dropwise over 5 min. The resulting mixture was allowed to warm up to room temperature over 1 h, then cooled again to 0 C. and treated with methyl 4-formylbicyclo[2.2.2]octane-1-carboxylate 15-A (Chapman, N. B. et al. J. Org. Chem., 1970, 35, 917) (2.5 g, 12.8 mmol). The reaction mixture was stirred at room temperature for 18 h then diluted with EtOAc (350 ml). The organic phase was washed with aqueous HCl (1 N), saturated aqueous sodium bicarbonate, and brine, then dried (Na2SO4) and concentrated in vacuo. The resulting solid was purified by flash silica gel chromatography, eluting with a gradient 0-4% EtOAc/hexanes. The resulting methyl 4-vinylbicyclo[2.2.2]octane-1-carboxylate 15-B was isolated as a clear, colorless oil.

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; Waddell, Sherman T.; Santorelli, Gina M.; Maletic, Milana M.; Leeman, Aaron H.; Gu, Xin; Graham, Donald W.; Balkovec, James M.; Aster, Susan D.; US2004/133011; (2004); 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. 36692-49-6, name is Methyl 3,4-diaminobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 36692-49-6

Example 21: 3-Amino-6-{4-[2-hydroxy-2-(2-phenyl-lN-benzoimidazol-5-yl)- ethylamino]-piperidin-1-yl}-4-propyl-thieno [2, 3-b] pyridine-2-carboxylic acid amide 0 0 o H i I so) Hunig’s base N -ire NH DCM 0 NH2 NH2 acetic acid H H THF / N N H min02 Mn02 N THE zon H 21 3,4-Diamino-benzoic acid methyl ester (2 g, 12.035 mmol) was dispersed in 40 mL DCM. Added hunig’s base (2.516 mL, 14.442 mmol) and stirred at RT until everything was in solution. Added benzoyl chloride (1.397 mL, 12.035 mmol) dropwise into the mixtuxe and stirred at RT for 1 hour. Added sat. NaHC03 aq. solution into the reaction mixture. Extracted with DCM three times. Combined all organic extracts and washed with brine. Dried over Na2SO4. Filtered and removed solvent in vacuo. Purified by flash chromatography using 10 % MeOH/DCM as eluent mixtures. 4-Amino-3-benzoylamino- benzoic acid methyl ester was trituated in hot ethyl acetate and 1.667 g (51.2 %) white solid was obtained.

The synthetic route of 36692-49-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM PHARMACEUTICALS, INC.; WO2005/56562; (2005); A1;,
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Application of 924-99-2, 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. 924-99-2, name is Ethyl 3-(dimethylamino)acrylate, This compound has unique chemical properties. The synthetic route is as follows.

a) Ethyl 2-[2,5-difluorobenzoyl]-3-dimethylamino-2-propenoate; A solution of 2,5-difluorobenzoyl chloride (5.26 g) in toluene (100 mL) was treated with ethyl-3-dimethylamino-2-propenoate (5.27 g), followed by triethylamine (5.9 mL). The mixture was stirred at 90C for 6.5 h then allowed to cool, and the precipitate removed by filtration. The filtrate was concentrated in vacuo to give a residue which was purified by flash chromatography (silica gel, 50-100% Et2O in petroleum ether [b.p. 40-600C]) to give the title compound as a yellow oil (0.95 g); ESMS m/z 284.2 [M+H]+, 306.1 [M+ Na]+.

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

Reference:
Patent; GLAXO GROUP LIMITED; WO2006/50940; (2006); 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. 13195-64-7, name is Diisopropyl malonate, A new synthetic method of this compound is introduced below., Formula: C9H16O4

Example 1Preparation of Protected Diester 2 The dihydroisoquinoline 1 (1.0 eq.) and Boc anhydride (1.5 eq.) were dissolved in CH2Cl2 at room temperature to provide a 1.5 M solution with respect to the dihydroisoquinoline. The mixture was allowed to stir for 30 min. Following the allotted time, the reaction mixture was cooled to 0° C. and then diisopropylmalonate (1.5 eq.) followed by a pre-chilled solution of the Pd catalyst (0.008 eq.) in dichloromethane were added successively to the reaction mixture to provide a final reaction concentration of 0.84 M with respect to the starting dihydroisoquinoline. The reaction mixture was allowed to continue stirring at 2.5° C. for 15 h. Following this time EtOAc and brine were added to the reaction mixture. The aqueous layer was extracted with three portions of EtOAc and the combined organic layers were dried (Na2SO4), filtered, and concentrated under reduced pressure to provide the crude product. The crude material was dissolved in a minimal amount of dichloromethane and purified by flash chromatography on SiO2 (15-30percent EtOAc-hexanes, elution was observed at 285 nm and 228 nm). The product 2 was a colorless solid that existed as a mixture of rotamers in solution at room temperature 94percent: [alpha]26D -69.0 (c 0.21, CHCl3); 1H NMR (CDCl3) delta 0.81-1.02 (m, 6H), 1.06-1.17 (m, 6H), 1.23-1.38 (m, 9H), 2.51-2.63 (m, 1H), 2.64-2.77 (m, 1H), 3.20-3.29 (m, 0.6H), 3.32-3.41 (m, 0.4H), 3.51-3.58 (m, 1H), 3.62-3.70 (m, 6H), 3.70-3.76 (m, 0.4H), 3.91-4.01 (m, 0.6H), 4.65-4.82 (m, 1H), 4.83-4.98 (m, 1H), 5.71 (apparent d, J=5.7 Hz, 0.6H), 5.78 (apparent d, J=7.9 Hz, 0.4H), 6.42-6.49 (m, 1H), 6.77 (s, 0.6H), 6.81 (s, 0.4H); 13C NMR (CDCl3) delta 21.02, 21.09, 21.18, 21.32, 27.24, 27.95, 28.02, 37.60, 39.34, 52.11, 52.83, 55.48, 55.52, 59.28, 60.08, 68.58, 68.76, 68.82, 79.46, 80.03, 110.09, 110.73, 111.13, 126.11, 126.18, 126.37, 127.07, 146.81, 146.87, 147.93, 153.86, 154.30, 166.29, 166.78, 166.94, 167.06.

The synthetic route of 13195-64-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GENERAL ELECTRIC COMPANY; US2008/306269; (2008); A1;,
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Reference of 36692-49-6,Some common heterocyclic compound, 36692-49-6, name is Methyl 3,4-diaminobenzoate, molecular formula is C8H10N2O2, 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 stirred suspension of methyl 3,4-diaminobenzoate (10.0 g, 60.2 mmol) and N-hydroxyethanimidamide (10.6 g, 95 % purity, 135 mmol) in dioxane (20 mL) was addedcaesium carbonate (19.6 g, 60.2 mmol) and the mixture was stirred at 110 C for 2 h. Water was added and the mixture was extracted with ethyl acetate. The organic phase was dried (sodium sulfate), filtered and the solvent was removed in vacuum to give a solid that was triturated with methanol to give 8.00 g (70 % yield) of the title compound.LC-MS (Method 2): R1 = 0.67 mm; MS (ESIpos): m/z = 191 [M+H]1H-NMR (400 MHz, DMSO-d6)oe [ppm]: 2.308 (16.00), 4.831 (2.74), 5.429 (3.11), 6.583 (2.69),6.603 (2.81), 7.148 (1.50), 7.153 (1.72), 7.169 (1.30), 7.174 (1.62), 7.212 (3.04), 7.217 (2.53).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 3,4-diaminobenzoate, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; SCHULZE, Volker; HEINRICH, Tobias; PRINZ, Florian; LEFRANC, Julien; SCHROeDER, Jens; MENGEL, Anne; BONE, Wilhelm; BALINT, Joszef; WENGNER, Antje; EIS, Knut; IRLBACHER, Horst; KOPPITZ, Marcus; BOeMER, Ulf; BADER, Benjamin; BRIEM, Hans; LIENAU, Philip; CHRIST, Clara; STOeCKIGT, Detlef; HILLIG, Roman; (1256 pag.)WO2017/102091; (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. 110661-91-1, name is tert-Butyl 4-bromobutanoate, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H15BrO2

Exemplification of General Procedure J:; Preparation of teri-butyl 4-(4-(3-(3-chloro-4-isopropoxyphenyl)-l,2,4-oxadiazol-5-yl)-l/7- indol-l-yl)butanoate; To a solution of 3-(3-chloro-4-isopropoxyphenyl)-5-(lH-indol-4-yl)-l,2,4-oxadiazole (0.100 g, 0.283 mmol) in DMF (0.999 mL) was added NaH (0.012 g, 0.311 mmol). After about 15 min tert- butyl 4-bromobutanoate (0.095 g, 0.424 mmol) was added and the reaction mixture was heated to about 50 C. After about 24 h the reaction mixture was cooled to ambient temperature, concentrated in vacuo and purified by chromatography on silica gel (eluting with EtOAc/Hep) to provide tert-butyl 4-(4-(3-(3-chloro-4-isopropoxyphenyl)-l,2,4-oxadiazol-5-yl)-lH-indol-l- yljbutanoate (0.135 g, 93%) as a colorless oil that solidified on standing. LC/MS (Table 1, Method c) Rt = 3.50 min, m/z 496 (M+H)+.

The synthetic route of 110661-91-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBOTT LABORATORIES; CUSACK, Kevin, P.; BREINLINGER, Eric, C.; FIX-STENZEL, Shannon, R.; STOFFEL, Robert, H.; WOLLER, Kevin, R.; WO2011/71570; (2011); A1;,
Ester – Wikipedia,
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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. 39149-80-9, name is tert-Butyl 2-bromopropanoate, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C7H13BrO2

General procedure: BuLi (1.6 M in hexane, 1.45 equiv) was added to a stirred solution of 3 in THF (0.022 M) at -78 C and the resultant mixture was stirred at -78 C for 1 h. The requisite electrophile was added and the resultant mixture was stirred at -78 C for 10 min, then MeOH was added. The reaction mixture was concentrated in vacuo and the residue was extracted with CH2Cl2, then filtered through basic alumina (grade V) and purified by flash column chromatography on basic alumina (grade I) to give 28-30.

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 39149-80-9.

Reference:
Article; Bashiardes, George; Bodwell, Graham J.; Collingwood, Stephen P.; Costello, James F.; Davies, Stephen G.; Fletcher, Ai M.; Garner, Alan; Preston, Simon C.; Thomson, James E.; Tetrahedron; vol. 70; 46; (2014); p. 8938 – 8951;,
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Adding a certain compound to certain chemical reactions, such as: 148547-19-7, name is Methyl 4-bromo-3-methylbenzoate, 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 148547-19-7, Formula: C9H9BrO2

A suspension of methyl 4-bromo-3-methylbenzoate (ABCR AV19078; 3 g; 13.10 mmol; 1 eq.), 2-(trifluoromethyl)phenylboronic acid (Aldrich 393606; 2.74 g; 14.41 mmol; 1.10 eq.), potassium carbonate (9.05 g; 65.48 mmol; 5 eq.) and tetrakis(triphenylphosphine)palladium(0) (1.51 g; 1.31 mmol; 0.10 eq.) in toluene (15 ml_) and water (15 ml_) was refluxed for 3 hours. The resulting mixture was filtered through a short pad of Celite, which was further washed with toluene. After evaporation of the solvent, the residue was taken up in ethyl acetate and washed successively with sat. aq. NaHCC>3, water and brine, dried over magnesium sulfate and concentrated in vacuo to afford the title compound (3.7 g, 96%) as a brown oil. HPLC (Method A) : Rt 5.34 min (purity 70.9%). LC/MS : 294.9 (M+H)+.

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; MERCK SERONO S.A.; WO2009/43890; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 3196-15-4,Some common heterocyclic compound, 3196-15-4, name is Methyl 2-bromobutyrate, molecular formula is C5H9BrO2, 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.

[286] Step 3: methyl 2-[5-bromo-2-(4-methylbenzoylimino)benzo[d]thiazol-3(2H)-yl]butanoate[287] To a stirred solution of N-(5-bromobenzo[d]thiazol-2-yl)-4-methylbenzamide (90 mg, 0.258 mmol) prepared in Step 2 in N,N-dimethylformamide (3.0 mL) were added methyl 2-bromobutyrate (93.9 mg, 0.519 mmol) and potassium carbonate (107 mg, 0.768 mmol). The reaction mixture was stirred at 80 ? for 3 hours. The reaction mixture was quenched with water and then extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered, and then evaporated. The residue was purified with silica gel column chromatography (n-hexane/ethyl acetate = 10/1) to give 109.5 mg of the titled compound as a white solid (Yield: 94%)[288] 1H NMR (CDCl3, 400 MHz) delta 8.18(d, 2H), 7.56(d, 1H), 7.42(s, 2H), 7.28(d, 2H), 5.46(brs, 1H), 3.67(s, 3H), 2.47-2.54(m, 2H), 2.42(s, 3H), 0.92(t, 3H)

The synthetic route of 3196-15-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; YUHAN CORPORATION; HUR, Youn; KIM, Dong-Hyun; KIM, Eun-Kyung; PARK, Jin-Hwi; JOO, Jae-Eun; KANG, Ho-Woong; OH, Se-Woong; KIM, Dong-Kyun; AHN, Kyoung-Kyu; WO2013/43001; (2013); A1;,
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Some common heterocyclic compound, 4341-76-8, name is Ethyl 2-butynoate, molecular formula is C6H8O2, 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. HPLC of Formula: C6H8O2

00727] (i) Production of ethyl 2-methylpyrazolo[l,5-a]pyridine-3-carboxylate [00728] To a suspension of 1-aminopyridinium iodide (125 g, 0.56 mmol) in N,N-dimethylformamide (1.2 L) were added ethyl 2-butynoate (54.0 g, 0.48 mmol) and potassium carbonate (79 g, 0.56 mmol) and the mixture was stirred at room temperature for 3 days. The reaction mixture was diluted with water (500 mL), ethyl acetate (500 mL) and hexane (500 mL), and the precipitated solid was collected by filtration, and washed with water (500 mL). The filtrate was extracted with a mixed solvent (1.5 L x 2) of ethyl acetate/hexane (1: 1) and dried over anhydrous magnesium sulfate, and the insoluble material was filtered off. The residue obtained by concentration of the filtrate and the solid collected by filtration in the above were combined, washed with diethyl ether (25 mL) and hexane (25 mL) and dried to give the title compound (36.0 g, 37%) as a white solid. The washing solution was concentrated, and the obtained residue was washed with diethyl ether (10 mL) and hexane (10 mL) and dried to give a second crop (11.0 g, 11%) of the title compound as a white solid. The washing solution of the second crop was concentrated, and the obtained residue was purified using a pad (elution solvent: ethyl acetate/hexane=l/l) with silica gel and activated carbon in 2 layers, washed with diethyl ether (5.0 mL) and hexane (5.0 mL) and dried to give a third crop (6.5 g, 7%) of the title compound as a white solid (total yield 55%).[00729] 1H-NMR (DMSOd6, 300 MHz) delta 1.35 (3H, t, J = 7.2 Hz), 2.57 (3H, s), 4.30 (2H, q, J = 7.2 Hz), 7.09 (IH, dt, J = 1.5, 6.9 Hz), 7.49 – 7.61 (IH, m), 8.00 (IH, td, J = 1.3 Hz), 8.75 (IH, td, J = 1.0, 6.9 Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4341-76-8, its application will become more common.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; TAKEDA PHARMACEUTICAL COMPANY LIMITED; BANNO, Hiroshi; HIROSE, Masaaki; KURASAWA, Osamu; LANGSTON, Steven, P.; MIZUTANI, Hirotake; SHI, Zhan; VISIERS, Irache; VOS, Tricia, J.; VYSKOCIL, Stepan; WO2010/90716; (2010); A1;,
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