Esters-buliding-blocks

Related Products of 99548-54-6,Some common heterocyclic compound, 99548-54-6, name is Methyl 3-bromo-2-methylbenzoate, molecular formula is C9H9BrO2, 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.

Example 110 methyl { (3S) -6- [ (3-bromo-2-methylbenzyl) amino] -2, 3-dihydro-l- benzofuran-3-yl } acetate; [0990][0991]Methyl 3-bromo-2-methylbenzoate (2.29 g, 10.0 mmol) was dissolved in tetrahydrofuran (50 mL) , under ice-cooling, lithium aluminum hydride (0.285 g, 7.50 mmol) was added by small portions, and the mixture was stirred under a nitrogen atmosphere for 2 hr. Sodium sulfate 10 hydrate (2.42 g, 7.50 mmol) was added to the reaction mixture, and the mixture was stirred at room temperature for 2 hr. Insoluble material was filtered off through celite, and the filtrate was concentrated under reduced pressure. The obtained solid was recrystallized from heptane-ethyl acetate to give 3-bromo-2-methylbenzyl alcohol (1.76 g, yield 88%) as colorless crystals. This product (0.943 g, 4.69 mmol) was dissolved in acetonitrile (25 mL) , a Dess-Martin reagent (2.39 g, 5.63 mmol) was added by small portions under ice-cooling, and the mixture was stirred at room temperature for 0.5 hr. The reaction mixture was treated with saturated aqueous sodium hydrogen carbonate and aqueous sodium thiosulfate solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. A solution of the obtained colorless oil, methyl [ (3S) -6-amino-2, 3-dihydro-l- benzofuran-3-yl] acetate (0.972 g, 4.69 mmol) and acetic acid(0.537 mL, 9.38 mmol) in acetonitrile (25 mL) was stirred under a nitrogen atmosphere at room temperature for 0.5 hr. Sodium triacetoxyborohydride (1.99 g, 9.38 mmol) was added to the reaction mixture, and the mixture was further stirred for 12 hr. The reaction mixture was treated with water and saturated aqueous ammonium chloride solution, and extracted with ethyl acetate. The extract was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate rhexane = 5:95-40:60) to give the title compound (1.59 g, yield 87%, 2 steps) as a colorless oil.1H NMR (300 MHz, CDCl3) delta 2.42 (3H, s) , 2.48-2.59 (IH, m) , 2.68-2.78 (IH, m) , 3.68-3.83 (4H, m) , 3.89 (IH, br s) , 4.18- 4.30 (3H, m) , 4.71 (IH, t, J = 9.1 Hz), 6.07-6.16 (2H, m) , 6.93 (IH, d, J = 8.0 Hz), 7.01 (IH, t, J = 7.9 Hz), 7.23-7.30(IH, m) , 7.49 (IH, dd, J = 7.9, 1.1 Hz). MS m/z 390 (M + H)+.

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-bromo-2-methylbenzoate, its application will become more common.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; NEGORO, Nobuyuki; TERAO, Yoshito; MIKAMI, Satoshi; YUKAWA, Tomoya; WO2010/143733; (2010); A1;,
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Synthetic Route of 90841-55-7, A common heterocyclic compound, 90841-55-7, name is Benzyl 3-bromopropanoate, molecular formula is C10H11BrO2, 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.

1,4, 7, 10-tetraazacyclododecane-l, 7-bis(t-butyl acetate), D02A tBu ester (leq., Macrcyclics) was dissolved in CH3CN (5ml) and benzyl 3-bromopropanoate was added in the presence of Et3N (2.1ml, 12mmol) at temp.0C. Reaction was slowly warmed up to room temp, and left stirring for 24h. After evaporation of the solvent under vacuum, product was purified by flash chromatography using 60N silica gel. Deprotection of benzyl ester groups was completed by catalytic hydrogenation under high pressure in the presence of Pd/C during 24h.

The synthetic route of 90841-55-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RADIOMEDIX INC.; TWOROWSKA, Izabela; SIMS-MOURTADA, Jennifer; DELPASSAND, Ebrahim, S.; WO2012/177701; (2012); A2;,
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Synthetic Route of 758684-29-6, A common heterocyclic compound, 758684-29-6, name is Methyl 3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylate, molecular formula is C10H11NO3, 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.

4-Methoxybenzaldehyde (31.5 mu,, 0.259 mmol) and acetic acid (50 0.873 mmol) were added to a solution of methyl 3,4-dihydro-2H-benzo[b][l,4]oxazine-6-carboxylate (50.0 mg, 0.259 mmol) in 1,2-dichloroethane (2 mL), and the reaction mixture was placed on a heater/shaker at 50 C for 2 hours. Sodium triacetoxyborohydride (137 mg, 0.647 mmol) was added, and the reaction was placed on the heater/shaker at 50 C overnight. The reaction was diluted with dichloromethane, washed with brine, and passed through an Isolute phase separator. The filtrate was concentrated and purified by column chromatography on silica gel (Biotage 10 gram column, eluting with 10-60% ethyl acetate-hexanes) to afford methyl 4-(4- methoxybenzyl)-3,4-dihydro-2H-benzo[b][l,4]oxazine-6-carboxylate which was used directly in the next step MS: (ES, m/z): 314 [M+H]+.

The synthetic route of 758684-29-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FORMA THERAPEUTICS, INC.; ZHENG, Xiaozhang; NG, Pui, Yee; THOMASON, Jennifer, R.; ZABLOCKI, Mary-Margaret; HAN, Bingsong; BARCZAK, Nicholas; LIU, Cuixian; RUDNITSKAYA, Aleksandra; LANCIA JR., David, R.; BAIR, Kenneth, W.; (315 pag.)WO2017/40963; (2017); A1;,
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Application of 4606-07-9,Some common heterocyclic compound, 4606-07-9, name is Ethyl cyclopropanecarboxylate, molecular formula is C6H10O2, 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.

EXAMPLE 10 3-(5-Cyclopropyl-1,2,4-oxadiazol-3-yl)-6-methoxy-5-morpholino-imidazo[1,5-a]quinazoline (Compound 70) A mixture of 6-methoxy-5-morpholino-imidazo[1,5-a]quinazoline-3-carboxamide oxime (0.9 g), ethyl cyclopropylcarboxylate (1.7 g), molecular sieves (3 g), and 80% sodium hydride (0.1 g) in 20 ml of dry DMF was heated for 11/2 hours at 120 C. The mixture was cooled to room temperature, diluted with acetic acid (0.5 ml) and methylene chloride (20 ml) and filtered. The filtered mixture was evaporated and the residue was purified by column chromatography (HPLC) (eluent: methylene chloride:acetone (2:1)) to give yellow crystals of the title compound, m.p. 227-228 C. Yield 0.38 g. In the same manner the following compound was prepared:

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

Reference:
Patent; Novo Nordisk A/S; US5371080; (1994); A;,
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These common heterocyclic compound, 57267-03-5, name is Ethyl 2,2,2-triethoxyacetate, 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: 57267-03-5

To a solution of 2M LDA in THF/hexane/ethylbenzene (6.4 ml, 12.8 mmol) in dry THF (15 ml) cooled to -78C under inert atmosphere was added 2-methylpyrimidine (0.60 g, 6.4 mmol). The RM was stirred for 1 h then ethyl 2,2,2-triethoxyacetate (1.31 ml, 7.0 mmol) was added. The solution was allowed to warm to RT and stirred for 3 days. The RM was poured into 1M HC1 and stirred for 1 h. The mixture was neutralised with NaHC03 solution and extracted three times with EtOAc. The combined organics were washed with brine, dried over Na2S04, filtered and evaporated. The crude was purified by FCC (0 – 50 % EtOAc in hexane) to give the title compound as a yellow solid. Y = 35 %. NMR (300 MHz, DMSO-) delta 13.63 (s, 1H), 8.89 (d, J= 5 Hz, 2H), 7.43 (t, J= 5 Hz, 1H), 6.52 (s, 1H), 4.29 (q, J= 7 Hz, 2H), 1.30 (t, J= 7 Hz, 3H).

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

Reference:
Patent; NODTHERA LIMITED; BOCK, Mark G.; WATT, Alan Paul; PORTER, Roderick Alan; HARRISON, David; (229 pag.)WO2019/25467; (2019); 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. 2905-65-9, name is Methyl 3-chlorobenzoate, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H7ClO2

General procedure: Cross-Coupling of ortho-, meta-, and para-Substituted, Electron-Rich and Electron-Deficient Aryl Halides and Aryl Mesylates with Aryl Neopentylglycolboronates Catalyzed by NiIICl(1-naph-thyl)(PCy3)2/PCy3 in Anhydrous THF at 23 C; General Procedure 2In an oven-dried test tube charged with a Teflon coated stirring barwere added aryl halide or aryl mesylate (0.3 mmol), aryl neopentyl-glycolboronates (0.315 mmol), K3PO4(H2O)3.2 (191.00 ¡À 1.00 mg, 0.9mmol), and NiIICl(1-naphthyl)(PCy3)2 (11.73 ¡À 0.0510 mg, 0.015mmol, 5% catalyst loading). The test tube was brought into a N2 filledglove box (moisture level <2 ppm) through three degassing cycles andPCy3 (8.4 mg, 0.03 mmol, 10% loading) ligand was added. Distilled sol-vent (1 mL) was added inside the glove box and the test tube wassealed by a rubber septum and left stirring at 23 C. A sample was tak-en by syringe and transferred outside the glove box. The sample wasdiluted by distilled THF (0.2 mL) and filtered through a short columnof Al2O3. The filtrate was concentrated and the GC analysis was car-ried out. The reaction mixture was diluted with CH2Cl2 (2 mL), filteredthrough a layer of Al2O3, and washed with CH2Cl2 (3 1 mL). The fil-trate was collected and concentrated under vacuum. The crude prod-uct was purified by column chromatography on silica gel with EtO-Ac/hexane mixture as eluent. The reductive elimination side-productwas also isolated and characterized. The synthetic route of 2905-65-9 has been constantly updated, and we look forward to future research findings. Reference:
Article; Malineni, Jagadeesh; Jezorek, Ryan L.; Zhang, Na; Percec, Virgil; Synthesis; vol. 48; 17; (2016); p. 2795 – 2807;,
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Adding a certain compound to certain chemical reactions, such as: 6942-37-6, name is Methyl 5-amino-2-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 6942-37-6, name: Methyl 5-amino-2-bromobenzoate

To a mixture of methyl5-amino-2-bromobenzoate 4a (0.436 g, 1.90 mmol), 2-bromoisobutyric acid 2b (0.479 g, 2.87 mmol) andanhydrous 2-PrOH (4.5 mL) was added Et3N (1.07 mL, 7.68 mmol), and the mixture was stirred for 19 hat 50 C. When the reaction was completed, the reaction mixture was evaporated under vacuum pressure.Water (30 mL) and 1M HCl (5 mL) were added and extracted with AcOEt (15 mL¡Á2). The combinedorganic layer was washed with brine and dried over anhydrous Na2SO4. After filtration, the organicsolution was concentrated to dryness under reduced pressure. The residue was was purified by columnchromatography to afford 9c as a pale yellow solution (0.407 g, 68%). 1H NMR (DMSO-d6, 400 MHz) delta:1.42 (s, 6H), 3.81 (s, 3H), 6.54 (dd, J = 8.8, 3.3 Hz, 1H), 6.88 (d, J = 3.3 Hz, 1H), 7.36 (d, J = 8.8 Hz, 1H),12.47 (s, 1H); 13C NMR (DMSO-d6, 100 MHz) delta: 25.52, 52.36, 56.04, 104.54, 115.26, 117.54, 132.11,133.83, 146.09, 166.57, 176.74; IR (KBr) cm-1: 1032, 1154, 1254, 1334, 1437, 1474, 1601, 1725, 2949,2991, 3388; HRMS (EI): calcd for C12H14BrNO4 [M+]: 315.0106. Found; 315.0090.

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:
Article; Kudo, Kazuhiro; Honda, Takahiro; Yamamoto, Noriyoshi; Heterocycles; vol. 91; 8; (2015); p. 1591 – 1602;,
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Synthetic Route of 35613-44-6, 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. 35613-44-6, name is Methyl 2-(2-aminophenyl)acetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

2-bromo-1-(3,4-dihydroisoquinolin-2(1H)-yl)ethanone (370 mg, 1.45 mmol), methyl 2-(2-aminophenyl)acetate (200 mg, 1.21) Methyl, anhydrous potassium carbonate (500 mg, 3.63 mmol) was added to acetonitrile (10 mL) successively, and the mixture was stirred and warmed at 80 C for 5 hours.. The TLC monitors the end of the reaction. The reaction mixture was cooled to room temperature, and the mixture was evaporated to dryness. Purification by crude silica gel column chromatography (petrole ether / ethyl acetate = 4 / 1) afforded 2-(2-((2-(3,4-dihydroisoquinolin-2(1Eta)yl)-2-oxoethyl)amino)phenyl)methyl acetate(N-001) was obtained as a pale yellow oil (150 mg, 31%).

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

Reference:
Patent; Shaoxing Cong Ling Pharmaceutical Technology Co., Ltd.; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Yang Huaiyu; (51 pag.)CN109020887; (2018); A;,
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These common heterocyclic compound, 23426-63-3, name is Methyl 2-bromo-2-methylpropanoate, 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: C5H9BrO2

To a solution of CH3ONa (587.78 mg, 10.88 mmol, 1.0 eq) in MeOH (20.0 mL) was addedmethyl 2-bromo-2-methyl-propanoate (1.97 g, 10.88 mmol, 1.41 mL, 1.0 eq) and tert-butyl Nhydroxy-N-methyl-carbamate (1.60 g, 10.88 mmol, 1.0 eq) at 15 C. The mixture was heated to 60 C with stirring for 16 h. TLC (PE: EtOAc = 5:1) showed that starting material was consumed completely and one main new spot formed. The mixture was evaporated to removethe solvent and get the residue. The residue was purified by column chromatography (5i02,Petroleum ether/Ethyl acetate=l0/l to 20/1) to obtain the title 0 (2.30 g, 9.30 mmol,85.49% yield) as off-white liquid. ?H NIVIR (4001V11{z, CHLOROFORM-d) = 3.74 (s, 3 H),3.11 (s, 3 H), 1.48 (d,J=4.9Hz, 15 H).

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

Reference:
Patent; NOVIRA THERAPEUTICS, INC.; KUDUK, Scott; HARTMAN, George, D.; (433 pag.)WO2018/5881; (2018); 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. 878207-28-4, name is Methyl 2-bromo-4,5-difluorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of Methyl 2-bromo-4,5-difluorobenzoate

A solution of phenylmethanol (4.32 g, 0.04 mol) in dry THF (250 mL) is added NaH (1.60 g, 0.04 mol, 60% in oil). The reaction mixture is stirred at 80 C for 2 h. Then the mixture is cooled and 2-bromo-4,5-difluorobenzoic acid methyl ester (10.0 g, 0.04 mol) is added at 0C. The reaction mixture wad stirred at 0C overnight. The solution is quenched with water (50 mL) and extracted with Et20 (60 mLx2). The combined organic layers are washed with saturated NaCl solution, dried over Na2S04 and concentrated under vacuum. The residue is purified by column chromatography on silica gel to give the desired product (9.00 g, 66 %).

The synthetic route of 878207-28-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; ANACOR PHARMACEUTICALS INC.; AKAMA, Tsutomu; JARNAGIN, Kurt; PLATTNER, Jacob J.; PULLEY, Shon Roland; WHITE, William Hunter; ZHANG, Yong-Kang; ZHOU, Yasheen; WO2014/149793; (2014); A1;,
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