Tag: M.W=100-200

Application of 31930-34-4,Some common heterocyclic compound, 31930-34-4, name is Ethyl cis-3-Bromoacrylate, molecular formula is C5H7BrO2, 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.

In a round-bottomed flask, at 0 C,were successively added Et3N (45 mL), F (5.25 g, 29 mmol), triisopropylsilylacetylene(6.5 mL, 29 mmol), PdCl2(PPh3)2 (330 mg, 0.5 mmol) and CuI (95 mg, 0.5 mmol). The mixture was stirred at 0 C for 4 h, then water (50 mL) was added. The crude was extracted with EtOAc(2 × 50 mL), washed with brine, dried over Na2SO4, filtered and concentrated in vacuum. After purification by chromatography on silica gel (cyclohexane/ethyl acetate 98:2), 6.6 g of an orange liquid were obtained (81% yield). 1H NMR (300 MHz, CDCl3) delta 6.14 (d, J = 11.7 Hz,1H), 6.05 (d, J = 11.7 Hz, 1H), 4.21 (q, J = 7.1 Hz, 2H), 1.27 (t, J = 7.1 Hz, 3H), 0.80-1.50 (m,21H). 13C NMR (126 MHz, CDCl3) delta 164.6, 129.4, 122.4, 105.1, 102.6, 60.5, 18.7, 14.4, 11.5. HRMS (ESI-TOF) m/z [M + Na]+ Calcd for C16H28NaO2Si 303.1751; Found 303.1764.

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

Reference:
Article; Fuentespina, Ruben Pomar; De La Cruz, Jose Angel Garcia; Durin, Gabriel; Mamane, Victor; Weibel, Jean-Marc; Pale, Patrick; Beilstein Journal of Organic Chemistry; vol. 15; (2019); p. 1416 – 1424;,
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These common heterocyclic compound, 455-75-4, name is Ethyl 3-amino-4-fluorobenzoate, 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: C9H10FNO2

To a stirred solution of [3-(1, 1-DIMETHYLETHYL)-1-ETHYL-4, 5-DIHYDRO-LH-PYRAZOLE-] 5-carboxylic acid (i. e. the product of Step D) (0.8 g, 4.1 mmol) in dichloromethane (5 mL) was added 1-propanephosphonic acid cyclic anhydride (50 wt % solution in ethyl acetate, 3.9 g, 6.14 mmol) followed by 4- (dimethylamino) pyridine [(0. 75] g, 6.14 mmol). After stirring for 1 h, ethyl [3-AMINO-4-FLUOROBENZOATE] (0.68 g, 3.7 mmol) was added, and the resulting solution was stirred at room temperature overnight. The solvent was removed in vacuo and partitioned between water (50 mL) and ethyl acetate (100 mL). The aqueous layer was extracted with ethyl acetate (30 mL). The organic layer was washed with aqueous saturated sodium bicarbonate (50 mL) and water (50 mL), and dried [(MGSO4).] The solvent was removed in vacuo to provide the title product, a compound of the present invention, as an oil (1.36 g). 1H NMR (CDC13): [B] 9.3 (s, 1H), 8.95 (d, 1H), 7.80 (m, 1H), 7.16 (t, 1H), 3.70 (t, 1H), 3.33 (dd, 1H), 3.18 (dq, 1H), 2.95 (dq, 1H), 2.83 (dd, 1H), 1.39 (t, 3H), 1.21 (t, 3H), 1.17 (s, 9H).

The synthetic route of Ethyl 3-amino-4-fluorobenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; E.I. DU PONT DE NEMOURS AND COMPANY; WO2004/35545; (2004); A2;,
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Related Products of 87661-20-9, A common heterocyclic compound, 87661-20-9, name is tert-Butyl cyclopropanecarboxylate, molecular formula is C8H14O2, 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.

Step 1; 4-(l-terf-Butoxycarbonyl-cyclopropyl)-4-hydroxy-piperidine-l-carboxylic acid benzyl ester: To a cooled (-780C) solution of 2.OM lithium dsopropylamide in heptane/ THF/ ethylbenzene (27.4 mL, 54.8 mmol) was added cyclopropanecarboxylic acid terf-butyl ester (7.08 g, 49.8 mmol) in THF (35 mL). After stirring at -780C for 1 h, a solution of 4-oxo-piperidine-l- carboxylic acid benzyl ester (11.6 g, 49.8 mmol) in THF (50 mL) was added. The reaction mixture was stirred at -780C for 3 h then warmed to room temperature. After stirring at ambient temperature for 16 h, the mixture was quenched with saturated aqueous solution of NH4Cl (150 mL) and extracted with EtOAc (150 mL x 3). The combined organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (0-40% EtOAc in Hexane) to yield 4-(l-tert-butoxycarbonyl- cyclopropyl)-4-hydroxy-piperidine-l-carboxylic acid benzyl ester (8.07 g, 43%). 1H NMR (400 MHz, CDCl3) delta 7.36-7.28 (m, 5H), 5.11 (s, 2H), 4.50 (s, IH), 4.00 (bis, 2H), 3.20 (brs, 2H), 1.72- 1.64 (m, 2H), 1.42 (s, 9H), 1.40-1.30 (m, 2H), 1.10 (dd, J=7.0 and 2.4 Hz, 2H), 0.88 (dd, J=7.0 and 2.4 Hz, 2H).

The synthetic route of 87661-20-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; H. LUNDBECK A/S; PETERSON, John; CHEN, Chien-an; CHEN, Bin; WU, Lingyun; SABIO, Michael; WO2010/53861; (2010); A2;,
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Related Products of 40872-87-5, These common heterocyclic compound, 40872-87-5, name is Methyl 3-amino-4-chlorobenzoate, 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.

It heated and dried at 120 degrees C under decompression of a p-toluenesulfonic-acid monohydrate (25.6g) for 1 hour. The methyl 3-amino-4-chlorobenzoate (10g) and the propiononitrile (20 ml) were added there, and it heated at reflux for 16 hours. After cooling a reaction mixture radiationally, the saturated sodium bicarbonate aqueous solution (250 ml) was added, and it stirred for 10 minutes. Ethyl acetate extracted, after carrying out decompression distilling off of the propiononitrile (50mlx3). The organic layer was dried and concentrated in vacuum with anhydrous sodium sulfate. Silica gel column chromatography (developing solvent: petroleum ether/ethyl acetate) refined the obtained residue, and it obtained the mark compound (8.5g).

The synthetic route of 40872-87-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUMITOMO DAINIPPON PHARMA COMPANY LIMITED; IKEDA, JUNYA; NAKAMURA, TAKANORI; OTAKA, HIROMICHI; (133 pag.)JP2016/28016; (2016); A;,
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Reference of 37746-78-4, 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 37746-78-4 as follows.

To a solution of ethyl 4-bromocrotonate 23 (0.9 mL, 5.18 mmol) in anhydrous dioxane (10 mL), palladium triphenyl phosphine tetrakis (300 mg, 0.26 mmol) was added to the round bottom flask. The flask was then evacuated three times at rt and backfilled with argon. The reaction mixture was allowed to stir for 15 min at rt then phenyl boronic acid (1.84 g, 10.36 mmol) and Na2CO3 (2.75 g, 25.9 mmol) were added under a positive pressure of argon. The reaction mixture which resulted was heated at reflux for 18 h and then cooled to rt. It was then passed through a short bed of celite. The celite bed was washed with EtOAc (50 mL) and the combined organic layers were washed with water (50 mL) and brine (30 mL). The organic layer was dried (Na2SO4) and concentrated under reduced pressure. The crude oil was purified by flash column chromatography (5% EtOAc in hexanes) on silica gel to afford ester 18 (893 mg, 70%). 1H NMR (300 MHz, CDCl3): delta 7.37 (d, J = 8.1 Hz, 2H), 7.14 (d, J = 7.8 Hz, 2H), 7.12 (d, J = 15.6 Hz, 1H), 5.85 (d, J = 15.3 Hz, 1H), 4.21 (q, J = 7.2 Hz, 2H), 3.52 (d, J = 6.9 Hz, 2H), 1.35 (S, 9H), 1.31 (t, J = 6.9 Hz, 3H); 13C NMR (75 MHz, CDCl3): delta 166.5, 149.6, 147.5, 134.7, 128.5, 125.6, 122.2, 60.2, 38.0, 34.4, 31.4, 14.3. HRMS (ESI) (M+Na)+, calcd for C16H22O2Na 269.1518; found 269.1512.

According to the analysis of related databases, 37746-78-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Tiruveedhula, V.V.N. Phani Babu; Witzigmann, Christopher M.; Verma, Ranjit; Kabir, M. Shahjahan; Rott, Marc; Schwan, William R.; Medina-Bielski, Sara; Lane, Michelle; Close, William; Polanowski, Rebecca L.; Sherman, David; Monte, Aaron; Deschamps, Jeffrey R.; Cook, James M.; Bioorganic and Medicinal Chemistry; vol. 21; 24; (2013); p. 7830 – 7840;,
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Adding a certain compound to certain chemical reactions, such as: 924-99-2, name is Ethyl 3-(dimethylamino)acrylate, 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 924-99-2, Product Details of 924-99-2

[1311] to a solution of ethyl 3-(dimethylamino)acrylate (165 mg, 1.2 mmol) and tea (233 mg, 2.3 mmol) in THF (15 ml) was added a solution of compound 277b (400 mg, 2.3 mmol) in THF (5 ml) drop-wise over 30 mins. The mixture was stirred at 20 C for 12 hours. The reaction mixture was concentrated under reduced pressure to give a residue. The residue was purified by preparatory-tlc (SiO2, petroleum ether: ethyl acetate = 1: 1) to give compound 277c (240 mg, yield: 44.4%) as a pale yellow oil. 1H NMR (400mhz, CDCl3) delta 8.94 (s, 1h), 7.51 – 7.36 (m, 2h), 7.21 – 7.14 (m, 1h), 7.13- 7.04 (m, 1h), 4.17 (q, 7 = 7.1 hz, 2h), 1.15 (t, 7 = 7.2 hz, 3h).

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; BLADE THERAPEUTICS, INC.; BUCKMAN, Brad, Owen; YUAN, Shendong; ADLER, Marc; EMAYAN, Kumaraswamy; MA, Jingyuang; (687 pag.)WO2018/64119; (2018); 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, Recommanded Product: Methyl 2-amino-3-methylbenzoate

A solution of methyl 2-amino-3-methylbenzoate (142.1 g, 0.843 mol, purity: 98% quantitative NMR) in 240 mL of H2O is gradually admixed at 30 C. with hydrogen bromide (48% of H2O, 149.2 g, 0.885 mol) added dropwise. The suspension obtained is admixed with hydrogen peroxide (30% in H2O, 105.1 g, 0.927 mol) added dropwise over 2 h, and the temperature is kept below 70 C. After 1 hour of subsequent stirring, NaHSO3 (39% in H2O, 33.7 g, 0.126 mol) is added a little at a time (peroxide test was negative). The suspension obtained is adjusted to pH7-8 with Na2CO3 (0.1 eq., 9.0 g, 0.084 mol), which is added a little at a time. Following filtration and drying in a vacuum drying cabinet, methyl 2-amino-5-bromo-3-methylbenzoate is isolated as a pale brown solid. Yield: 204.2 g, 97.7% of theory, purity: 98.5% quantitative NMR). 1H NMR (600 MHz, (d6-DMSO): delta=7.70 (d, 1H), 7.36 (pt, 1H), 6.63 (br s, 2H), 3.80 (s, 3H), 2.12 (s, 3H)).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2-amino-3-methylbenzoate, and friends who are interested can also refer to it.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; Volz, Frank; Himmler, Thomas; Mueller, Thomas Norbert; Lehmann, Sandra; Von Morgenstern, Sascha; Moradi, Wahed Ahmed; Pazenok, Sergii; Lui, Norbert; US2014/148611; (2014); A1;,
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Application of 4630-82-4,Some common heterocyclic compound, 4630-82-4, name is Methyl cyclohexanecarboxylate, molecular formula is C8H14O2, 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 for the catalytic hydrogenation of methyl benzoate as substrate: Under argon, a Keim autoclave was charged with [Ru Cl2(R-BINAP)(dm02] (0.01 mmol, 0.05 mol %) and S,S-DPEN (0.01 mmol, 0.05 mol %) followed by THF (2 ml) and the solution stirred for 5 minutes. Then a solution of the desired ester (20 mmol) in THF (2 ml), followed by more THF (2×1 ml), and a solution of tridecane (1 mmol) in THF (2 ml), as internal standard, followed by more THF (2×1 ml), were successively added to the autoclave. Finally, solid NaOMe (1 mmol, 5 mol %) was added and the autoclave was pressurised with hydrogen gas at 50 bars and placed in a thermostatted oil bath set at 60 C. After the mentioned time, the autoclave was removed from the oil bath, and cooled in a cold-water bath. Then, an aliquot (0.4 ml) was taken, diluted with MTBE (5 ml), washed with aq. sat. NH4Cl (5 ml), and filtered over a plug of celite and analyzed by GC.

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

Reference:
Patent; Saudan, Lionel; Saudan, Christophe; Saudan, Michel Alfred Joseph; Saudan, Sylvia Joyeuse Adelaide Ada; US2010/286452; (2010); A1;,
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Some common heterocyclic compound, 20754-20-5, name is Methyl 3-(p-tolyl)acrylate, molecular formula is C11H12O2, 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. Application In Synthesis of Methyl 3-(p-tolyl)acrylate

A method for constructing a quaternary carbon ring by visible light catalysis [2+2] reaction, comprising the following steps: The ruthenium complex 1 was used as a visible light catalyst, and 1.3 mg of the catalyst and 0.2 mmol were added to 2 mL of 1,4-dioxane.(E)-methyl-3-p-tolyl acrylate(corresponding R2 is p-tolyl and R3 is methoxy), wherein the concentration of the visible light catalyst is 1.0 x 10-3 M. Argon gas was introduced for ten minutes, and then light-illuminated in an argon atmosphere at 25 ° C for 36 hours with Blue LEDs of 450 nm ± 10 nm. After the reaction was completed, the mixture was directly dried and separated by column. Nuclear magnetic resonance, carbon, and mass spectrometry identify products as racemic(1R, 2R, 3S, 4S)-dimethyl-3,4-di-p-methylphenylcyclobutane-1,2-dicarboxylate. The conversion of the starting material was 100percent and the yield of the cyclobutane product was 90percent.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 20754-20-5, its application will become more common.

Reference:
Patent; Chinese Academy Of Sciences Physics And Chemistry Technology Institute; Wu Lizhu; Lei Tao; Zhao Leimin; Zhou Chao; Liu Zan; Tong Zhenhe; (89 pag.)CN108623425; (2018); A;,
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Synthetic Route of 4630-80-2, The chemical industry reduces the impact on the environment during synthesis 4630-80-2, name is Methyl cyclopentanecarboxylate, I believe this compound will play a more active role in future production and life.

To LDA (17.03 ml, 17.03 mmol) (1M in THF) at 0 oc was addedmethyl cyclopentanecarboxylate (1.75 g, 13.6 mmol) and the mixture stirred for 5 min. Asolution of 4-(bromomethyl)-1-chloro-2-(3-methoxypropoxy)benzene (2 g, 6.8 mmol) in THF(5ml) was added dropwise then the mixture was allow to warm toRT. The mixture wasquenched with ice and NH4CI (aq), and then extracted with EtOAc. The organics werecombined, dried (brine, Na2S04), and concentrated to an oil. The oil was purified on silicagel hex:EtOAc (eluting at -1 0%) to give methyl 1-(4-chloro-3-(3- methoxypropoxy)benzyl)cyclopentane-1-carboxylate (2.28 g, 6.69 mmol, 98% yield) as ayellow oil. LCMS (ESI) (m/z): 363.3 (M+23t.

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 cyclopentanecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; CATALANO, John G.; DICKSON, Hamilton D.; KAZMIERSKI, Wieslaw Mieczyslaw; LEIVERS, Martin R.; WEATHERHEAD, John Gordon; (389 pag.)WO2018/154466; (2018); A1;,
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