Tag: M.W=200-300

Synthetic Route of 609-12-1,Some common heterocyclic compound, 609-12-1, name is Ethyl 2-bromo-3-methylbutanoate, molecular formula is C7H13BrO2, 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.

Reference Example 6; Ethyl 3-methyl-2-(5-phenyl-1,1-dioxothieno[2,3-d]isothiazol-2(3H)-yl)butyrate; The compound of Reference Example 5 (67 mg) and sodium hydride (13 mg, Wako Pure Chemical Industries, Ltd., containing 40% mineral oil) were dissolved in N,N-dimethylformamide (1 ml), and the resultant solution was stirred at 60 C. for 1 hour. Then, ethyl 2-bromoisovalerate (68 mul, manufactured by Wako Pure Chemical Industries, Ltd.) was added thereto and the reaction solution was further stirred for 24 hours. The reaction mixture was stood to cool to room temperature and then concentrated, and ethyl acetate (2 ml) and water (2 ml) were added thereto. A product was extracted with ethyl acetate, washed with saturated saline, dried with magnesium sulfate and then concentrated. The obtained residue was put into a silica gel column (hexane:ethyl acetate=5:1) to give 16 mg of the titled compound. LC-MS: HPLC retention time 4.94 minutes (LC Condition 2), m/z 380 (MH+)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 2-bromo-3-methylbutanoate, its application will become more common.

Reference:
Patent; Asahi Kasei Pharma Corporation; US2009/192154; (2009); A1;,
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Synthetic Route of 148547-19-7, A common heterocyclic compound, 148547-19-7, name is Methyl 4-bromo-3-methylbenzoate, molecular formula is C9H9BrO2, 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-Bromo-3-methylbenzylalcohol (4) A solution of methyl 4-bromo-3-methylbenzoate (2.0 g, 8.7 mmol) in dry THF (10 mL) was added to an ice-cooled suspension of lithium aluminiumhydride (400 mg, 10.4 mmol) in dry THF (30 mL). After addition, the mixture was warmed to room temperature and then stirred for 3 h. The excess lithium aluminiumhydride was quenched by successive addition of water (0.4 mL), 15% NaOHaq (0.4 mL), and water (1.2 mL) under ice cooling. The insoluble material appeared was removed by filtration (celite), and the precipitate was washed by AcOEt (20 mL*5). The combined filtrates were washed with brine (50 mL) and then dried over Na2SO4. The solvent was evaporated, and the obtained product (1.6 g, 100%) was used for next step without further purification. 1H-NMR (CDCl3, 400 MHz): delta7.53 (1H, d, J=8.1 Hz), 7.26 (1H, d, J=1.5 Hz), 6.40 (1H, dd, J=8.1, 1.5 Hz), 4.68 (2H, s), 2.44 (3H, s).

The synthetic route of 148547-19-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHANG, Christopher J.; VAN DE BITTNER, Genevieve V.; HIRAYAMA, Tasuku; CHAN, Jefferson; US2014/51863; (2014); A1;,
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These common heterocyclic compound, 2876-78-0, name is Methyl 1-Naphthaleneacetate, 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. Product Details of 2876-78-0

General procedure: Aryl acetate 1a (2.0 mmol, 1.0 equiv.), CuO (0.2 mmol, 0.1equiv.) and aq TBHP (6.0 mmol, 3.0 equiv.) were added to aflask connected to a reflux condenser. The flask was heated at 110 C for 4.5 h and then cooled to room temperature.Pyridine (0.5 mL, 3.0 equiv.) was added and the mixture washeated to 50 C and stirred for 4.0 h. Thereafter, an aqueoussolution of Na2S2O3 (0.5 mol L-1, 10.0 mL) was added, andthe mixture was extracted with EtOAc (¡Á3). The organiclayers were combined, washed with brine, dried overanhydrous Na2SO4, filtered, concentrated and purified byflash column chromatography over silica gel (200-300 mesh) using petroleum ether/EtOAc (25:1) to afford thedesired compound 2a (172.3 mg, 53% yield) as a colourlessoil.

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

Reference:
Article; Jiang, Jin; Journal of Chemical Research; vol. 48; 7-8; (2019); p. 235 – 240;,
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Synthetic Route of 148547-19-7, These common heterocyclic compound, 148547-19-7, name is Methyl 4-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.

Pottasium Ferrocyanide trihydrate (3.70 g, 17.5 mmol) was added to a solution of 4-bromo-3-nnethyl-benzoic acid methyl ester (4.00 g, 17.46 mmol) in dimethylacetamide (10 ml_), followed by sodium carbonate (1 .85 g, 17.5 mmol) and palladium acetate (78 mg, 0.35 mmol). This mixture was heated at 12O0C for 15 hours, after which time it was quenched onto water (150 ml_) and extracted with tert-butylmethylether (3 x 50 ml_). The combined organic extracts were washed with water (150 ml_), dried over magnesium sulphate, filtered and evaporated under reduced pressure to give a solid (2.53 g, 83%). 1H NMR (400 MHz, CDCI3): delta 2.60 (s, 3H), 3.95 (s, 3H), 7.65 (d, 1 H), 7.95 (m, 1 H), 8.00 (d, 1 H).

Statistics shows that Methyl 4-bromo-3-methylbenzoate is playing an increasingly important role. we look forward to future research findings about 148547-19-7.

Reference:
Patent; PFIZER LIMITED; GIBSON, Karl Richard; GREEN, Martin Peter; UNDERWOOD, Toby James; WAKENHUT, Florian; WO2010/32200; (2010); A1;,
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Application of 15448-76-7, These common heterocyclic compound, 15448-76-7, name is Dimethyl bicyclo[2.2.1]heptane-1,4-dicarboxylate, 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 dimethyl bicyclo[2.2.1]heptane-l ,4-dicarboxylate (1.5 g, 7.07 mmol), chromium(VI) oxide (4.24 g, 42.4 mmol) in acetic acid (15 mL) was heated at 90 C for 14 hours. The reaction mixture was diluted with ethyl acetate, washed with water, saturated NaHCC>3 and brine, dried (Na2SO/t), and concentrated. The residue was purified bychromatography eluting with 10-60% ethyl acetate in heptane to give the title compound (400 mg, 25% yield).JH NMR (400 MHz, CDC13) delta ppm 3.78 (d, J = 5.2 Hz, 6H), 2.67 (dd, J = 18.0, 2.5 Hz, 1H), 2.44 – 2.32 (m, 2H), 2.32 – 2.16 (m, 3H), 1.98 – 1.78 (m, 2H).

The synthetic route of 15448-76-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CALICO LIFE SCIENCES LLC; ABBVIE INC.; MARTIN, Kathleen, Ann; SIDRAUSKI, Carmela; PLIUSHCHEV, Marina, A.; FROST, Jennifer, M.; TONG, Yunsong; BLACK, Lawrence, A.; XU, Xiangdong; SHI, Lei; ZHANG, Qingwei, I.; CHUNG, Seungwon; XIONG, Zhaoming; SWEIS, Ramzi, Farah; DART, Michael, J.; BROWN, Brian, S.; MURAUSKI, Kathleen; (673 pag.)WO2019/90069; (2019); A1;,
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Adding a certain compound to certain chemical reactions, such as: 135908-43-9, name is Methyl 4-aminobicyclo[2.2.2]octane-1-carboxylate hydrochloride, 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 135908-43-9, COA of Formula: C10H18ClNO2

(l-Cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-mo holino-carbenium hexafluorophosphate (COMU, 1181 mg, 2.76 mmol) was added to a N,N-dimethylformamide (6 mL) solution of Hunig’s base (1.47 mL, 8.40 mmol), methyl 4-aminobicyclo[2.2.2] octane- 1- carboxylate hydrochloride (527 mg, 2.40 mmol, ArkPharm), and 2-(4-chloro-3- fluorophenoxy)acetic acid (515 mg, 2.52 mmol) that was kept stirring at 0 C. The ice bath was removed, and the reaction was left stirring at ambient temperature for 1 hour. The resulting solution was filtered through a glass microfiber frit and purified by preparative HPLC [YMC TriArt C18 Hybrid 5 mupiiota column, 50 x 100 mm, flow rate 70 mL/minute, 5-100% gradient of acetonitrile in buffer (0.1 % trifluoroacetic acid)] to give the title compound (0.78 g, 2.11 mmol, 88 % yield).JH NMR (400 MHz, DMSO-+) m/z 370 (M+H)+.

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 4-aminobicyclo[2.2.2]octane-1-carboxylate hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CALICO LIFE SCIENCES LLC; ABBVIE INC.; MARTIN, Kathleen Ann; SIDRAUSKI, Carmela; FROST, Jennifer M.; TONG, Yunsong; XU, Xiangdong; SHI, Lei; XIONG, Zhaoming; (165 pag.)WO2019/90090; (2019); A1;,
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Electric Literature of 2967-66-0, 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 2967-66-0 as follows.

General procedure: Hydrazine hydrate 64% (v/v) (30.0 mL, 0.33 mol) was heated up to 50-60 C. The methyl ester 3 (0.01 mol) was added and the mixture was heated at reflux for 10 min. The cooling was performed sequentially in water bath, followed by ice bath and dry ice-ethanol bath. The precipitate was filtered and washed with cold water.

According to the analysis of related databases, 2967-66-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ishii, Marina; Jorge, Saloma?o Do?ria; De Oliveira, Alex Alfredo; Palace-Berl, Fanny; Sonehara, Ieda Yuriko; Pasqualoto, Kerly Fernanda Mesquita; Tavares, Leoberto Costa; Bioorganic and Medicinal Chemistry; vol. 19; 21; (2011); p. 6292 – 6301;,
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Synthetic Route of 54535-22-7,Some common heterocyclic compound, 54535-22-7, name is Diethyl 2-((phenylamino)methylene)malonate, molecular formula is C14H17NO4, 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.

Step B: Diethyl N-methyl-N-phenylaminomethylenemalonate To 10 mmol of the compound obtained in the previous Step, dissolved in tetrahydrofuran, there are added, slowly (in small portions) and under an inert atmosphere, 12 mmol of 95% NaH and then, dropwise, 30 mmol of iodomethane. The reaction mixture is then stirred, at ambient temperature and under an inert atmosphere, for 12 hours. 1 mL of methanol is added in order to neutralise the excess of sodium hydride. The solution is then concentrated in vacuo, and then water is added to the residual oil obtained. After extraction with dichloromethane, the combined organic phases are dried, filtered and concentrated under reduced pressure to yield the expected product in the form of a colourless oil. MS (EI, m/z): 276 (M+).

The synthetic route of 54535-22-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Brion, Jean-Daniel; Israel, Lucien; Le Ridant, Alain; Harpey, Catherine; Rabhi, Cherif; Kaloun, El Bachir; US2006/63801; (2006); A1;,
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Adding a certain compound to certain chemical reactions, such as: 35450-36-3, name is Methyl 2-bromo-5-methoxybenzoate, 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 35450-36-3, Recommanded Product: 35450-36-3

Intermediate 11 :Methyl 2-bromo-5-methoxy benzoate (20.0 g, 81.61 mmol), tri methyl bo roxine (13.36 ml_, 97.93 mmol), Pd(dppf)CI2 (1.0 g, 1.36 mmol), dioxane (350 ml_), water (50 ml_), and Cs2CO3 (22.5 g, 163 mmol) were stirred at 11OC (oil bath) under nitrogen for 16 hours. After cooling, the solid was removed by filtration. The solution was concentrated and purified by SGC (10:1 EtOAc/hexanes) to give 11 (12.1 g, 80%). Mass calculated for formula C10H12NO3 , 180.20, observed LCMS m/z 181.20 (M+H).NMR (H1); 2.35(3H,CH3) 3.73(3H, – OCH3),3.88(3 H, CO2-CH3),6.86-7.5(m,3H,Aromatic)

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; SCHERING CORPORATION; WO2009/14637; (2009); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 35450-36-3, 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. 35450-36-3, name is Methyl 2-bromo-5-methoxybenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

a) 2-[(E)-2-(3-Chlorophenyl)vinyl]-5-methoxybenzoic acid methyl ester To a stirred solution of 2-bromo-5-methoxybenzoic acid methyl ester (17.7 g, 72.2 mmol) and 3-chlorovinylbenzene (9.17 mL, 72.2 mmol) in anhydrous acetonitrile (180 mL) was added triethylamine (20.10 mL, 144 mmol) and tris(o-tolyl)phosphine (2.85 g, 9.38 mmol). The reaction mixture was sparged with argon for 5 min, palladium(II) acetate (1.62 g, 7.22 mmol) was added and the mixture heated at 85 C. under an argon atmosphere for 21 h. The product mixture was filtered through celite, concentrated in vacuo, the residue dissolved in ethyl acetate (400 mL) and washed with 1 N HCl (aq.) (200 mL) and brine (200 mL). The combined aqueous layers were back-extracted with ethyl acetate (200 mL). The ethyl acetate extracts were combined, dried (MgSO4) and concentrated under reduced pressure to give the crude 2-[(E)-2-(3-chlorophenyl)vinyl]-5-methoxybenzoic acid methyl ester as a red-brown, viscous oil which was used in the next step without further purification. Data for 2-[(E)-2-(3-chlorophenyl)vinyl]-5-methoxybenzoic acid methyl ester: 1H NMR (300 MHz, CDCl3): delta 7.91 (d, 1H), 7.63 (d, 1H), 7.49 (dd, 1H), 7.44 (d, 1H), 7.41 (ddd, 1H), 7.26 (d, 1H), 7.21 (ddd, 1H), 7.08 (dd, 1H), 6.83 (d, 1H), 3.94 (s, 3H), 3.86 (s, 3H) ppm.

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-bromo-5-methoxybenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; N.V. Organon; US2008/64678; (2008); A1;,
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