Tag: M.W=200-300

Related Products of 150529-73-0,Some common heterocyclic compound, 150529-73-0, name is Methyl 2-(3-bromophenyl)acetate, 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.

Tributyltin methoxide (28.3 mL, 98 mmol), the product of preparation 8 (15.0 g, 65mol), isopropenyl acetate (10.8 mL, 98 mmol), palladium (II) acetate (750 mg, 3.30 mmol) and tri-ortho-tolylphosphine (2.0 g, 6.5 mmol) were stirred together in toluene (75 mL) at 100C for 5 hours. After cooling, the reaction was diluted with ethyl acetate (150 mL) and 4M aqueous potassium fluoride solution (90mL), and stirred for 15 minutes. The mixture was filtered through Arbocele and the organic phase was separated and concentrated in vacuo. The residue was then purified by column chromatography on silica gel eluting with diethyl ether : pentane, 0: 100 to 25: 75, followed by dichloromethane to give the title compound as a pale yellow oil in 94% yield (12.6 g). 1H NMR (400MHz, CDCI3) : 6 : 2.15 (3H, s), 3.61 (2H, s), 3.69 (5H, s), 7.10-7. 13 (2H, m), 7.19 (1H, d), 7. 30 (1H, t). LRMS ESI : m/z 229 [M+Na] +.

The synthetic route of 150529-73-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER LIMITED; PFIZER INC; WO2005/92860; (2005); 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. 6279-86-3, name is Triethyl methanetricarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of Triethyl methanetricarboxylate

Preparation of ethyl 1-hexyl-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylate In a round-bottomed flask equipped with a condenser, N-hexylaniline (355 mg, 2 mmol) is added to a solution of methanetricarboxylic acid triethyl ester (1.35 ml, 6.4 mmol). The resulting reaction mixture is placed in a CEM Discovery microwave oven and irradiated in the open round-bottomed flask, and then the ethanol formed is distilled off (the parameters are the following: power=250 W, temperature=225 C., execution time=5 min, hold time=15 min). After microwave heating, the reaction crude is purified on a chromatographic column, with petroleum ether, ethyl acetate at 4:1. The crystalline product obtained is dried to give the compound: yield=430 mg (69%). 1H NMR (CDCl3): delta 8.16 (d, J=8 Hz, 1H), 7.64 (m, 1H), 7.27-7.19 (m, 2H), 4.48 (q, J=8 Hz, 2H), 4.18 (t, J=8 Hz, 2H), 1.72-0.86 (m, 14H).

The synthetic route of 6279-86-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; Ruat, Martial; Faure, Helene; Gorojankina, Tatiana; Mann, Andre; Taddei, Maurizio; Manetti, Fabrizio; Solinas, Antonio; US2013/267559; (2013); A1;,
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Adding a certain compound to certain chemical reactions, such as: 126541-82-0, name is Methyl 3-amino-4-(trifluoromethyl)benzoate, 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 126541-82-0, Formula: C9H8F3NO2

Step A: Methyl 3-bromo-4-(trifluoromethyl)benzoatet-BuONO (79.0 g, 765 mmol) was added to a solution of methyl 3-amino-4- (trifluoromethyl)benzoate (67.0 g, 306 mmol) and CuBr (88.0 g, 612 mmol) in acetonitrile (1000 mL) at 0 C, and the resulting mixture was warmed to 25 C and stirred for 12 h. The mixture was then poured into EtOAc (600 mL) and filtered. The filtrate was washed with an aqueous HCl solution (1 M, 200 mL x 3), then brine (200 mL), dried over Na2S04 and concentrated. The residue was purified by column chromatography on silica gel (PE:EA = 200: 1) to give the title compound. MS: mlz = 283, 285 (M + 1). *H NMR (400 MHz, CDC13) delta 8.37 (s, 1H), 8.06 (d, J = 8.0 Hz, 1H), 7.77 (d, J= 8.0 Hz, 1H), 3.97 (s, 3H).

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 3-amino-4-(trifluoromethyl)benzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MSD R&D (CHINA) CO., LTD.; MITCHELL, Helen; FRALEY, Mark, E.; COOKE, Andrew, J.; CHEN, Yi-Heng; STUMP, Craig, A.; ZHANG, Xu-Fang; MCCOMAS, Casey, C.; SCHIRRIPA, Kathy; MCWHERTER, Melody; MERCER, Swati, P.; BABAOGLU, Kerim; MENG, Dongfang; WU, Jane; LIU, Ping; WOOD, Harold, B.; BAO, Jianming; LI, Chun Sing; MAO, Qinghua; QI, Zhiqi; (263 pag.)WO2015/148344; (2015); A2;,
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Reference of 541-16-2, These common heterocyclic compound, 541-16-2, name is Di-tert-Butyl malonate, 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: alpha,beta-Unsaturated aldehyde (3.0 mmol) and malonate (3.0 mmol) were added into asolution of TiCl4 (6.0 mmol) in CCl4 (2.0 mL) and THF (10 mL) at 0 C, Then, pyridine (0.96 mL, 12.0 mmol) in THF (2 mL) was added dropwisely over 1 h. The resulting mixture was stirred at room temperature overnight. After quenched with water, the mixture was extracted with ethyl acetate, dried over Na2SO4, filtered and concentrated under vacuum. The residue was purified by silica gel chromatography with hexane/ethyl acetate = 20/1 to afford the product.

The synthetic route of 541-16-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wei, Xu; Lu, Junzhu; Duan, Wei-Liang; Synthesis; vol. 48; 23; (2016); p. 4155 – 4160;,
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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. 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. Computed Properties of C9H9BrO3

Under an argon atmosphere, 2.300 g (approx. 10.298 mmol) of the compound from example 51A was dissolved in 20 ml toluene and 2.103 g (8.585 mmol) of methyl-2-bromo-5-methoxybenzoate, 2.551 g (12.014 mmol) potassium phosphate, 0.346 g (1.159 mmol) of (2-biphenyl)di-tert.- butylphosphine and 0.173 g (0.772 mmol) of palladium(II) acetate were added. The mixture was boiled under reflux overnight. After cooling, it was extracted with ethyl acetate. The combined organic phases were washed with water, dried over sodium sulfate and concentrated in a rotary evaporator at reduced pressure. The residue was purified by preparative HPLC (eluent: acetonitrile/water, gradient 10:90 ? 90:10). We obtained 135 mg (4% of theor.).LC-MS (method 4): R, = 1.28 min; MS (EIpos): m/z = 368 [M+H]+.1H-NMR (400 MHz, DMSO-D6): delta [ppm] = 2.20 (s, 3H), 3.70 (s, 3H), 3.80 (s, 3H), 3.84 (s, 3H), 6.07 (s, IH), 7.04 (dt, IH), 7.11 (dd, IH), 7.16-7.24 (m, 2H), 7.30 (d, IH), 7.34 (dd, IH), 7.41-7.46 (m, IH), 9.14 (sbr, IH).

The synthetic route of 35450-36-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; BAeRFACKER, Lars; KAST, Raimund; GRIEBENOW, Nils; MEIER, Heinrich; KOLKHOF, Peter; ALBRECHT-KUePPER, Barbara; NITSCHE, Adam; STASCH, Johannes-Peter; SCHNEIDER, Dirk; TEUSCH, Nicole; RUDOLPH, Joachim; WHELAN, James; BULLOCK, William; PLEASIC-WILLIAMS, Susan; WO2010/20363; (2010); A1;,
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Electric Literature of 55666-43-8,Some common heterocyclic compound, 55666-43-8, name is tert-Butyl 3-bromopropanoate, 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.

To a solution of 2,2,2-trifluoro-N-(trans-2-phenylcyclopropyl)-N-(piperidin-4-ylmethyl)acetamide (300 mg, 0.919 mmol) in acetonitrile (10 mL) was added potassium carbonate (381 mg, 2.76 mmol) followed by tert-butyl 3-bromopropanoate (211 mg, 1.011 mmol) was heated in a seal tube at 80 C. for 4 hours. The reaction mixture was filtered, and the filtrate evaporated to dryness. The resulting oil was dissolved in 2 ml of EtOH and 2 ml of 1 M NaOH. The reaction mixture was stirred for 20 min. The solution injected on a preparatory HPLC (2 to 10% AcCN: H2O with 0.1% formic acid modifier). The fractions were collected. To each fraction was added 0.1 ml of 6 M HCl, and the fractions were evaporated to dryness. Acid was formed by deprotection of t-butyl during evaporation. 3-(4-(((trans-2-phenylcyclopropyl)amino)methyl)piperidin-1-yl)propanoic acid (140 mg, 0.354 mmol, 38.5% yield) was isolated as yellow oil. 1H NMR (400 MHz, METHANOL-d4) delta 7.29-7.37 (m, 2H), 7.11-7.29 (m, 3H), 3.65 (br. s., 2H), 3.45 (t, J=7.07 Hz, 2H), 3.23 (d, J=5.81 Hz, 2H), 3.11 (br. s., 2H), 3.04 (dt, J=4.01, 7.89 Hz, 1H), 2.90 (t, J=7.07 Hz, 2H), 2.62 (ddd, J=3.54, 6.63, 10.29 Hz, 1H), 2.04-2.29 (m, 3H), 1.70 (dd, 2H), 1.62 (ddd, J=4.42, 6.51, 10.55 Hz, 1H), 1.42 (q, J=6.91 Hz, 1H); LC-MS Rt=0.42 min; MS (ESI): 303.3 [M+H]+.

The synthetic route of 55666-43-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GlaxoSmithKline Intellectual Property (No. 2) Limited; Johnson, Neil W.; Kasparec, Jiri; Rouse, Meagan B.; Tian, Xinrong; Miller, William Henry; Suarez, Dominic; (79 pag.)US9346840; (2016); B2;,
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Related Products of 176694-36-3, 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. 176694-36-3, name is Methyl 4-fluoro-3-(trifluoromethyl)benzoate, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of methyl 4-fluoro-3-(trifluoromethyl)benzoate (9.60 g, 43.2 mmol) in N,N-dimethylformamide (100 mL) was added mercaptan sodium (3.33 g, 47.5 mmol) at 0 C. by small portions, and the resulting mixture was stirred at room temperature for 2 hr. The reaction mixture was diluted with ethyl acetate, washed twice with water and once with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was recrystallized from hexane to give the title compound (10.1 g, yield 93%) as colorless crystals.melting point 76-77 C.1H NMR (CDCl3) delta 2.57 (3H, s), 3.94 (3H, s), 7.36 (1H, d, J=8.3 Hz), 8.11 (1H, dd, J=1.9, 8.3 Hz), 8.27 (1H, d, J=1.9 Hz).Elemental analysis (for C10H9F3O2S)Calculated (%): C, 48.00; H, 3.63.Found (%): C, 47.97; H, 3.62.

The chemical industry reduces the impact on the environment during synthesis Methyl 4-fluoro-3-(trifluoromethyl)benzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Itoh, Fumio; US2010/69381; (2010); A1;,
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These common heterocyclic compound, 53518-15-3, name is 7-Amino-4-(trifluoromethyl)-2H-chromen-2-one, 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. HPLC of Formula: C10H6F3NO2

EXAMPLE 61 Preparation of 7-[N’-(3,5-diaminopyrazol-4-ylidene)hydrazino]-4-trifluoromethylchroman-2-one In a manner similar to that described in Example 2, 7-[N’-(3,5-diaminopyrazol-4-ylidene)hydrazino]-4-trifluoromethylchroman-2-one was prepared from 7-amino-4-trifluoromethylchromen-2-one (0.25 g), malononitrile (0.15 g) and hydrazine hydrate (0.3 mL). The title compound (0.101 g) was isolated after purification by column chromatography.

The synthetic route of 7-Amino-4-(trifluoromethyl)-2H-chromen-2-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhang, Zaihui; Daynard, Timothy Scott; Sviridov, Serguei V.; Chafeev, Mikhail A.; Wang, Shisen; US2003/60453; (2003); A1;,
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Application of 6279-86-3,Some common heterocyclic compound, 6279-86-3, name is Triethyl methanetricarboxylate, molecular formula is C10H16O6, 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: To a solution of carbonyl compound (1.0-2.0 equiv) in CH2Cl2 or 1,2-dichloroethane, Tf2CHCH2CHTf2(5, 0.50 mmol) was added at room temperature. After stirring at room temperature to 80 C, the reaction mixture was concentrated under reduced pressure. The resultant residue was purified by bulb-to-bulb distillation using a Kugelrohr oven to give bis(triflyl)ethylated product 4.

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

Reference:
Article; Yanai, Hikaru; Fujita, Masaya; Takahashi, Arata; Zhang, Min; Mishima, Masaaki; Kotani, Akira; Matsumoto, Takashi; Taguchi, Takeo; Molecules; vol. 18; 12; (2013); p. 15531 – 15540;,
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Electric Literature of 474709-71-2,Some common heterocyclic compound, 474709-71-2, name is Ethyl 4-bromo-2-fluorobenzoate, molecular formula is C9H8BrFO2, 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 solution LHMDS (38 mL, 1 M solution) in THF (40 mL) cooled to -78C, was added acetonitrile (2.1 mL, 40.5 mmol) drop-wise. The reaction was stirred at -78C for 60 min, and a solution of ethyl 4-bromo-2-fluorobenzoate (Example 286, 5 g, 20.2 mmol) in THF (10 mL) was added. The reaction mixture was left to warm to rt over 16 h. Then, NH4CI (50 mL, 10% aqueous solution) was added, and the organic solvent was removed under reduced pressure. The resulting aqueous suspension was filtered, and the filter cake was washed successively with water and ether, and then dried under mechanical vacuum at 40C to give the desired product (4.4 g). EI-MS m/z [M+Hf 241.2, GCMS RT 12.64 min.

The synthetic route of 474709-71-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2006/34491; (2006); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics