Tag: M.W=100-200

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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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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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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Synthetic Route of 1559-02-0, These common heterocyclic compound, 1559-02-0, name is Diethyl 1,1-cyclopropanedicarboxylate, 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 mixture of diethyl 1 ,1-cyclopropanedicarboxylate (10.0 g, 53.7 mmol) in ethanol (70 mL) and water (35 mL) was added sodium hydroxide (2.1 g, 53.7 mmol). The reaction was stirred at 25 C for 16 h and diluted with ethyl acetate (60 mL). The organic layer was discarded. The aqueous phase was adjusted to pH = 3 by addition of aqueous hydrochloric acid (4 M). The mixture was extracted with ethyl acetate (3 x 80 mL). The combined organic layers were washed with brine (30 mL), dried over sodium sulfate and concentrated under reduced pressure to give crude 1- ethoxycarbonylcyclopropanecarboxylic acid (6.6 g, 78%) as a colorless oil. NMR (400MHz, CDCl3) delta 12.86 (br s, 1H), 4.31 – 4.17 (m, 2H), 1.87 – 1.81 (m, 2H), 1.77 – 1.69 (m, 2H), 1.32 – 1.24

The synthetic route of 1559-02-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; PATEL, Snahel; HAMILTON, Gregory; ZHAO, Guiling; CHEN, Huifen; DANIELS, Blake; STIVALA, Craig; (358 pag.)WO2019/12063; (2019); A1;,
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Adding a certain compound to certain chemical reactions, such as: 22223-49-0, name is Methyl 2-amino-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 22223-49-0, HPLC of Formula: C9H11NO2

N-Bromosuccinimide (38.5 g, 216 mmol) was added to a mixture consisting of methyl 2-amino-3-methylbenzoate (32.4 g, 196 mmol, Intermediate 89: step a) and dichloromethane (300 mL). The resultant reaction mixture was stirred at room temperature for 16 hours before it was poured into water (200 mL) and the aqueous phase was extracted with dichloromethane (200 mL*3). The combined organic extracts were dried over Na2SO4, filtered and concentrated to dryness under reduced pressure to afford the title compound.

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; JOHNSON & JOHNSON; LEONARD, KRISTI A.; BARBAY, KENT; EDWARDS, JAMES P.; KREUTTER, KEVIN D.; KUMMER, DAVID A.; MAHAROOF, UMAR; NISHIMURA, RACHEL; URBANSKI, MAUD; VENKATESAN, HARIHARAN; WANG, AIHUA; WOLIN, RONALD L.; WOODS, CRAIG R.; FOURIE, ANNE; XUE, XIAOHUA; CUMMINGS, MAXWELL D.; MCCLURE, KELLY; TANIS, VIRGINIA; US2015/111870; (2015); A1;,
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Synthetic Route of 106-32-1, A common heterocyclic compound, 106-32-1, name is Ethyl octanoate, molecular formula is C10H20O2, 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.

General procedure: Ester, ruthenium catalyst , metal alkoxide co-catalyst (used as a solid or some alcoholic solution) and optionally solvent (see Table 1) were loaded altogether in an 100 mL or 1L autoclave equipped with a mechanical stirring device, pressure and internal temperature sensors and a heating/cooling system for internal temperature regulation. Sealed autoclave was then purged under stirring with nitrogen (3 times 5 bars) and hydrogen (3 times 5 bars) before being pressurized to required hydrogen pressure via an hydrogen tank equipped with a way out pressure regulator and also an internal pressure sensor to follow and determine hydrogen consumption. Reaction mixture was then heated to required temperature and hydrogen pressure into the autoclave was maintained to the desired value during the whole reaction. Upon reaction completion also determined by GC analysis with complete disappearance of both starting material and mixed ester coming from transesterification reaction with product and eventually with metal alkoxide co-catalyst and/or alcoholic solvent, autoclave was then cooled down to 25 C. It was then depressurized and purged with nitrogen (3 times 5 bars) and reaction mixture was then transferred to a round-bottomed flask and lights compounds were removed under vacuum. Crude product was then flash distilled in order to determine the quantity of residues formed during the reaction and yield was calculated based on GC purity of distilled product.

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; FIRMENICH SA; DUPAU, Philippe; BONOMO, Lucia; KERMORVAN, Laurent; HALDIMANN SANCHEZ, Murielle; (46 pag.)WO2019/175158; (2019); A1;,
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Adding a certain compound to certain chemical reactions, such as: 14064-10-9, name is Diethyl 2-chloromalonate, 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 14064-10-9, Application In Synthesis of Diethyl 2-chloromalonate

3-Bromobenzenecarbothioamide (1.00 g, 4.62 mmol) and diethyl chloropropanedioate (1.0 mL, 6.0 mmol) were dissolved in dioxane (35 mL). The mixture was heated at 80¡ãC and stirred overnight, whereupon the solvent was removed under vacuum. Ethyl 2-(3-bromophenyl)-4-hydroxy-1 ,3-thiazole-5-carboxylate was obtained as a yellow solid (1.09 g, 72percent) by trituration in acetonitrile. An oven-dried Schlenk tube equipped with a magnetic stir bar was charged with 1.5 mL of an aqueous solution of K2CO3 (2M, 3.0 mmol), tetrakis(triphenylphosphine)palladium(0) (140 mg, 0.121 mmol) and toluene (3 mL). The tube was capped with a rubber septum and immersed in an oil bath at 80 ¡ãC for 30 min. Ethyl 2-(3′-bromophenyl)-4-hydroxy-1 ,3- thiazole-5-carboxylate (188 mg, 0.575 mmol) and 2-trifluoromethyl-phenylboronic acid (218 mg, 1.15 mmol) were then added, and the reaction mixture stirred at 80¡ãC. Upon complete consumption of the starting material (12 h), as judged by thin-layer chromatography analysis, the reaction mixture was filtered on a celite pad. The filtrate was diluted with ethyl acetate, and extracted with water. The organic layers were further washed with brine and dried over sodium sulfate. The product was isolated by column chromatography (hexanes/EtOAc) as a yellow solid (56 mg, 25percent). 1H-NMR (DMSO-cie) delta (ppm): 10.82 (br s, 1 H), 7.96 (d, 2H, J=8.11), 7.86 (d, 2H, J=7.57), 7.78-7.73 (m, 1 H), 7.67-7.62 (m, 1 H), 7.47-7.41 (m, 2H), 4.16 (q, 2H, J=7.03), 1.24 (t, 3H, J=7.03).

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; DOMPE’ S.P.A.; MORICONI, Alessio; BIANCHINI, Gianluca; COLAGIOIA, Sandro; BRANDOLINI, Laura; ARAMINI, Andrea; LIBERATI, Chiara; BOVOLENTA, Silvia; WO2013/92711; (2013); A1;,
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Application of 106-32-1, A common heterocyclic compound, 106-32-1, name is Ethyl octanoate, molecular formula is C10H20O2, 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.

Dissolve 0.155037g (0.00189mol, 0.02eq) of sodium acetate and 0.100161g (0.000945mol, 0.01eq) of sodium carbonate in 5mL of water, add 100mL of ethanol, and add the colorless liquid product obtained in step (a) (containing 0.0945mol of compound 2. Based on 1.0eq), react at 40 C for 2.5 hours. During the reaction, 6.2676g (0.094878mol, 1.004eq) hydroxylamine aqueous solution was added dropwise. After the reaction was completed, it was filtered and distilled under reduced pressure to remove ethanol. After adding 100 mL of water, the temperature was lowered to 0 C, and then slowly added dropwise sulfuric acid to adjust the pH to 3.5 to precipitate a white solid, which was filtered, washed with water, and dried to obtain 14.415 g of a white solid. Based on octanoyl hydroxamic acid, the white The purity of the solid was 99.9%, and the yield was 95.7%.

The synthetic route of 106-32-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Heze Xin Eastern Countries Rihua Technology Co., Ltd.; Xue Tianhui; Chen Xiaohui; Chen Kun; Qin Lijin; (12 pag.)CN110845367; (2020); A;,
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Reference of 32122-09-1, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 32122-09-1 name is Ethyl 2-(benzyloxy)acetate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

EXAMPLE 83 Preparation of 2-benzyloxyacetyl-gamma-butyrolactone: A solution of 10.6 ml of diisopropylamine in 75 ml of tetrahydrofuran was chilled to -70 C., and 46 ml of a 1.6N hexane solution of n-butyllithium were added dropwise to the solution. After completion of the addition, the mixture was stirred for 15 minutes, and a solution of 54.8 g of gamma-butyrolactone in 50 ml of tetrahydrofuran was added dropwise over 55 minutes, and the mixture was stirred for 50 minutes. Further, a solution of 14.75 g of ethyl benzyloxyacetate in 50 ml of tetrahydrofuran was added, and the resultant mixture was stirred for 2.5 hours at -60 to -50 C. 5N hydrochloric acid was then added so as not to exceed 20 C. to adjust the pH of the mixture to 1-2. Ethyl acetate was added to the reaction system, and the resultant mixture was washed with a saturated saline solution. The organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The thus-obtained crude product was subjected to column chromatography on silica gel (elution solvent: hexane:ethyl acetate=3:1?2:1?1:1) to obtain 13.01 g (yield: 87.2%) of the intended product as a colorless oil. 1 H-NMR (CDCl3, ppm): 2.30(1H,m), 2.75(1H,m), 3.88(1H,m), 4.27-4.47(4H,m), 4.68(2H,s), 7.29-7.38(5H,m).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 2-(benzyloxy)acetate, and friends who are interested can also refer to it.

Reference:
Patent; Pola Chemical Industries, Inc.; US5942515; (1999); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 110928-44-4, 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. 110928-44-4, name is trans-Methyl 4-(hydroxymethyl)cyclohexanecarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of compound 14 ( 17.26 g) in THF (450 ml_) stirred at 0 C was added triethylamine (39.4 ml284.5 mmol) followed by methanesulfonyl chloride (14.9 ml151.7 mmol). The mixture was stirred at 0 C for additional 10 min then the reaction mixture was stirred at room temperature for 2 h . The reaction mixture was filtered through a Celite (0,01-0,04 mm) bed that was then washed with fresh TH F; the resulting solution was evaporated under reduced pressure to give 15 as a yellow oil (30.95 g) that was employed in the following reaction without further purification. Quantitative yield . Analytical data : Mr: 250.30 (C10H 18O5S) and 13C-NMR and MS are compatible with the structure

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, trans-Methyl 4-(hydroxymethyl)cyclohexanecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRACCO IMAGING SPA; MAIOCCHI, Alessandro; VISIGALLI, Massimo; BELTRAMI, Lorena; SINI, Loredana; LATTUADA, Luciano; WO2013/135750; (2013); A1;,
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Ester – an overview | ScienceDirect Topics