Tag: M.W=200-300

Application 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.

Step 7.1 : (preparation of a compound of formula (XI)) 3-(2-Hydroxy-2-methylpropylamino)propionic acid tert-butyl ester 1 g of 1 -aminomethylpropan-2-ol (1 1 .22 mmol) is placed in 10 ml of DMF. 1 .58 ml of triethylamine (1 1 .22 mmol) and 1 .87 ml of tert-butyl 3-bromopropionate (1 1.22 mmol) prediluted in 5 ml of DMF are successively added dropwise. After stirring for 18 hours at room temperature, the solvent is evaporated off. The residue is chromatographed on silica gel with a gradient of from 0% to 20% MeOH in DCM to give 2 g of 3-(2-hydroxy-2- methylpropylamino)propionic acid tert-butyl ester.

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

Reference:
Patent; SANOFI; BRAUN, Alain; CRESPIN, Olivier; FORICHER, Yann; MARCINIAK, Gilbert; MUZET, Nicolas; NICOLAI, Eric; PASCAL, Cecile; VIVET, Bertrand; VIVIANI, Fabrice; WO2013/111106; (2013); A1;,
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Reference of 75567-84-9,Some common heterocyclic compound, 75567-84-9, name is Methyl 3-(4-bromophenyl)propanoate, molecular formula is C10H11BrO2, 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.

Methyl 3-(4-bromophenyl)propanoate (1a) (1.0 g, 4.11 mmol) was dissolved in 7mL ofN,N?-dimethylformamide (DMF). Copper (I) iodide (156 mg, 0.82 mmol),triethylamine (TEA 1.2mL, 8.23mmol), tetrakis (triphenylphosphine) palladium (0)Pd(PPh3)4 475 mg, 0.41 mmol, trimethylsilylacetylene (TMSA 0.74 mL, 5.35mmol) were added and the reaction mixture was stirred at 80 C under Ar until all thestarting material was consumed, as was monitored by TLC. The reaction mixture wasfiltered through a pad of celite and organic solvent (ethyl acetate: n-hexane = 10:1) wasadded. The organic phase was washed two times with saturated ammonium chloride,brine and then dried over magnesium sulfate. The solvent was evaporated to yield theproduct 740 mg and it was used to next without further purification.

The synthetic route of 75567-84-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ebara, Yasuhito; Hayashi, Tenko; Hori, Sakiko; Kaihatsu, Kunihiro; Kato, Nobuo; Ogata, Katsuya; Okazaki, Miku; Sawada, Shinjiro; Takagi, Kenji; Molecules; vol. 25; 4; (2020);,
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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. 457097-93-7, name is Methyl 4-amino-3-(trifluoromethoxy)benzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 457097-93-7

To a 500 mL round-bottom flask was added methyl 4-amino-3- (trifluorornethoxy)benzoate (7.1 g, 30.19 mmol, 1.0 equiv.), AcOH (100 mL), and NaSCN (12.1 g, 149.25 mmol, 5.0 equiv.) followed by the dropwise addition of bromine (9.6 g, 60.07 mmol, 2.0 equiv.) in AcOH (50 mL) at 0 C over a 1 h. The mixture was stirred at 0 C for 2 h, and then at 40 C overnight. The reaction mixture was again cooled to 0 C, and NaSCN (12.2 g, 150.49 mmol, 5.0 equiv.) was added, followed by the dropwise addition of bromine (9.6 g, 60.07 mmol, 2.0 equiv.) in AcOH (50 mL) over a 1 hr period. The reaction mixture was stirred at 0 C for 2 h, then at 40 C for 3 days. The resulting mixture was diluted with water (200 mL) and the pH value of the solution was adjusted to 9 using sodium hydroxide. The resulting solids were collected by filtration, washed with water (20 ml x 2), and dried in an oven at 60 C for 6 h to provide methyl 2-amino-4-(trifluoromethoxy)-l,3-benzothiazole-6-carboxylate A4b (5.4 g, 61%) as a brown solid.

The synthetic route of 457097-93-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARDELYX, INC.; CHAO, Jianhua; JAIN, Rakesh; HU, Lily; LEWIS, Jason Gustaf; BARIBAULT, Helene; CALDWELL, Jeremy; (249 pag.)WO2018/39384; (2018); 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. 52727-57-8, name is Methyl 2-amino-5-bromobenzoate, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H8BrNO2

A suspension of methyl 2-amino-5-bromobenzoate (460 mg, 2.0 mmol), potassium acetate (441 mg, 4.5 mmol) and pinacol diborane (1.52 g, 6.0 mmol) in 1,4-dioxane (20 mL) was degassed under a flow of N2 for 15 minutes. PdCb(dppf) (73 mg, 0.1 mmol) was added and the mixture heated to 95C for 16 hours. The reaction was deemed complete by LCMS. After cooling, the contents were partitioned between CH2C12 and water. The organic layer was washed with water, dried over anhydrous MgS04, filtered and evaporated. The product was purified by automated silica-gel chromatography eluting with a hexanes/EtOAc gradient. The fractions containing methyl 2- amino-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)benzoate were concentrated to yield the product as a colorless oil = 560 mg (2.00 mmol, quant.). (0566) LC/MS – HPLC (254 nm) – Rt 3.32 min. MS (ESI) m/z 278.3 [M + H]+.

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; SIGNALRX PHARMACEUTICALS, INC.; MORALES, Guilermo, A.; GARLICH, Joseph, R.; DURDEN, Donald, L.; (166 pag.)WO2018/140730; (2018); A1;,
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Application of 874649-82-8,Some common heterocyclic compound, 874649-82-8, name is Methyl 6-fluorochroman-2-carboxylate, molecular formula is C11H11FO3, 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.

Example4: Synthesis of 4hioro-3, 4-dihydro–2Wchromene4–carb&dehyde of Formu1using Vitride in presence of IPA:A solution of methyl (50gm, 0238 moles) in Methylene dichioride (MDC) (500m1) is prepared under nitrogen atmosphere and cooled to 48C. In another flask 100 ml Toluene is added in 86.7 gm of 70% Sodium bis(2 methoxyethoxy)aluminium dihydride (vitride) solution in toluene under nitrogen atmosphere andcooled to 05C. In this solution of vitride 12.63 ml of IPA is added slowly at 05C. This vitride PA solution is added in reaction mass in 34 hrs at 43 to 48C. After the end of addition reaction mass is stirred for 0.5 hrs and then added 22.97 ml IPA at 43 to 48C. Reaction mass then quenched with 130 ml of 15% aqueous HCI solution at 43 to 48C. 250 ml water s added. Organic layer separated at RT and Aqueous layer is washed with 250 ml MDC. Finalorganic layer containing Methyl 6tuoro34dihydro2H-chromene-2-carhaldehyde is washed wti 375 m ounned water and dried over 20 gm sodun suiphatrr HPLC purity- Formula-i 85.94%, hormuia-2-1 1.08%, NOeld 99.01%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 6-fluorochroman-2-carboxylate, its application will become more common.

Reference:
Patent; CADILA PHARMACEUTICALS LIMITED; MODI, Rajiv Indravadan; ISMAILI, Aminmahamad Nasiruddin; RAUT, Dipak Bhikanrao; MANSURI, Javedhusen Karimbhai; DESAI, Chaitanya Chhotubhai; WO2014/111903; (2014); A2;,
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Synthetic Route of 41841-16-1, 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. 41841-16-1, name is Methyl 2-(4-bromophenyl)acetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Methyl 4-bromophenylacetate (0.9 g, 4.5 mmol) was dissolved in chloroform (30 mL).Add NBS (0.3g, 4.5mmol),Stir at 70 C for 2 hours.After the reaction solution is diluted, it is washed with water.The mixture was washed with saturated brine, dried over anhydrous sodium sulfate and evaporated.Purified by silica gel column chromatography,A colorless liquid (0.5 g, 38%) was obtained.

The synthetic route of Methyl 2-(4-bromophenyl)acetate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Xiangjin Biological Technology Co., Ltd.; Sun Fang; Zhan Youni; (53 pag.)CN108341814; (2018); A;,
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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 721-63-1 as follows. SDS of cas: 721-63-1

A 100 mL two-necked reaction flask was placed in an ice bath at 0 C, p-trifluoromethylphenylacetate 2i (10.0 mmol) and 20 mL of acetonitrile were added, and p-toluenesulfonyl azide 3a (11.0 mmol) was added.1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (15.0 mmol) was slowly added.Stir for 5 minutes in an ice bath and place in a microwave reactor.Set power 400W, heating temperature 40 C, heating time 60 min,Turn on the exhaust fan.After the reaction is completed, the mixture is cooled to room temperature, quenched by the addition of ammonium chloride solution, and extracted with dichloromethane and water. The organic phase is collected, dried over anhydrous sodium sulfate, filtered, and evaporated. Chromatography (eluent is petroleum ether (60-90 C) / ethyl acetate, v / v = 80:1),The red solid target product 1i (2.06 g, yield 80%) was obtained.The target product was confirmed by nuclear magnetic resonance spectroscopy and high resolution mass spectrometry.

According to the analysis of related databases, 721-63-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Nanjing Tech University; Gao Zhen; Yi Xiangyan; Huang Fei; Huang He; Yu Yang; Zhang Zhipeng; Xue Lian; Wang Lize; Qiao Nasen; (12 pag.)CN108727216; (2018); A;,
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Synthetic Route of 206548-14-3, A common heterocyclic compound, 206548-14-3, name is Methyl 2-amino-5-bromo-3-methylbenzoate, molecular formula is C9H10BrNO2, 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 solution of 5.0g (0.021 mol) of 2-amino-5-bromo-3-methyl-benzoic acid methyl ester and 2.8g (0.023 mol) of phenyl boronic acid in 150 mL of dimethoxyethane was added 20.5 mL of a 2.0M aqueous solution of Na2CO3 and 1.18g (1.02 mmol) of Pd(PPh3)4. The reaction mixture was evacuated and filled with N2 three times and was then heated to reflux overnight. The reaction was then cooled to room temperature, and poured into ethyl acetate and water. The aqueous layer was extracted three times with ethyl acetate. The combined organics were washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was chromatographed on silica gel using gradient elution (100% hexane to 4/1 hexane/ethyl acetate) to provide 2.5 g (50%) of 4-amino-5-methyl-biphenyl-3-carboxylic acid methyl ester. Electrospray Mass Spec: 241.8 (M+H)+

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; Wyeth Holdings Corporation; EP1144369; (2004); B1;,
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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. 792-74-5, name is Dimethyl [1,1′-biphenyl]-4,4′-dicarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of Dimethyl [1,1′-biphenyl]-4,4′-dicarboxylate

The detailed procedure is as follows; to the solution of MBPDC (600 mg, 2.22 mmol) in 40 mL acetic acid, 20 mL of4:1 (v/v) H2SO4/H2O solution was added. Then the reaction mixture was refluxed for 24 h at 120C. The product was washed thoroughl ywith ethanol and dried in oven at 80¡ãC overnight (Yield: 520 mg,96.6percent).

The synthetic route of 792-74-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Medabalmi, Veerababu; Ramanujam, Kothandaraman; Journal of the Electrochemical Society; vol. 164; 7; (2017); p. A1720 – A1725;,
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Adding a certain compound to certain chemical reactions, such as: 619-42-1, name is Methyl 4-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 619-42-1, HPLC of Formula: C8H7BrO2

[0246] Step 1: 4-Bromobenzohydrazide : To a stirred solution of methyl 4- bromobenzoate (10 g, 46.51 mmol) in methanol (200 mL) was added hydrazine hydrate (23.2 g, 465.1 mmol) at rt. The mixture was then refluxed for 16 h. The mixture was concentrated, diluted with water (70 mL) and extracted with ethyl acetate (3 X 70 mL). The combined organic layers were washed with brine (30 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was triturated with diethyl ether (30 mL) to afford 4-bromobenzohydrazide (8 g, 37.38 mmol, 80% yield ) as an off white solid . XH NMR (300 MHz, DMSO-d6) delta 7.68-7.53 (m, 4H), 7.38 (br s, 1H), 4.10 (br+2H]+.

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; KALYRA PHARMACEUTICALS, INC.; HUANG, Peter Qinhua; KAHRAMAN, Mehmet; SLEE, Deborah, Helen; BUNKER, Kevin, Duane; HOPKINS, Chad, Daniel; PINCHMAN, Joseph, Robert; ABRAHAM, Sunny; SIT, Rakesh, Kumar; SEVERANCE, Daniel, Lee; (248 pag.)WO2016/161160; (2016); A1;,
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