Tag: M.W=100-200

3196-15-4, 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 3196-15-4 as follows.

Potassium carbonate (8.7 g, 63 mmol) was added to a solutionof 3-bromo-8-methylquinolin-6-ol (7, 5.0 g, 21 mmol) in 70 ml ofN,N-dimethylformamide. After the addition of methyl 2-bromobutyrate(7.1 g, 38 mmol), the reaction mixture was stirred for 16 h atroom temperature. Subsequently the mixture was filtered and thefiltrate was diluted with ethyl acetate. This organic phase waswashed with water and brine, dried over magnesium sulfate andevaporated under reduced pressure. The residue was purified bychromatography on silica gel, using ethyl acetate and cyclohexaneas eluents to yield 2-(3-bromo-8-methylquinolin-6-yloxy)-butyricacid methyl ester (8, 6.5 g, 19 mmol, 91%). 1H NMR (CDCl3):d = 1.04 (t, 3H, J = 7.3 Hz), 1.99 (q, 2H, J = 7.1 Hz), 2.68 (s, 3H),3.70 (s, 3H), 4.63 (t, 1H, J = 7.7 Hz), 6.65 (d, 1H, J = 2.3 Hz), 7.22(d, 1H, J = 2.2 Hz), 8.06 (d, 1H, J = 2.1 Hz), 8.68 (d, 1H, J = 2.1 Hz).LC-MS: Rt = 1.12 min; MS: m/z = 340 [M+1]+, 341 [M+2]+.

According to the analysis of related databases, Methyl 2-bromobutyrate, the application of this compound in the production field has become more and more popular.

Reference:
Article; Lamberth, Clemens; Kessabi, Fiona Murphy; Beaudegnies, Renaud; Quaranta, Laura; Trah, Stephan; Berthon, Guillaume; Cederbaum, Fredrik; Knauf-Beiter, Gertrud; Grasso, Valeria; Bieri, Stephane; Corran, Andy; Thacker, Urvashi; Bioorganic and Medicinal Chemistry; vol. 22; 15; (2014); p. 3922 – 3930;,
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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. 344-14-9, name is Dimethyl 2-fluoromalonate, A new synthetic method of this compound is introduced below., 344-14-9

General procedure: In a 50 mL two-necked flask containing dichloromethane (10 mL) were added the amine (17 mmol) followed by the aldehyde (15 mmol) and the resulting reaction mixture was allowed to stir at rt for 2 h, before the fluorinated dicarbonyl system (10 mmol) was added. The reaction mixture was stirred at rt for 16 h, evaporated and the residue dissolved in dichloromethane (20 mL), washed with distilled water (2¡Á20 mL), dried over magnesium sulfate and evaporated, to give the desired product. Further purification by distillation or column chromatography eluting from hexane/ethyl acetate was carried out when appropriate. Analytical and spectroscopic data for each individual compound are listed below. For NMR data only resonances of one diastereoisomer or conformer is given for clarity.

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:
Article; Lisse, Etienne; Sandford, Graham; Journal of Fluorine Chemistry; vol. 206; (2018); p. 117 – 124;,
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Some common heterocyclic compound, 105-53-3, name is Diethyl malonate, molecular formula is C7H12O4, 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. 105-53-3

To a solution of diethyl malonate (3.2 g, 20 mmol) and anhydrous potassium carbonate powder (6.9 g, 50 mmol) in DMF (50.0 mL) was added 1,2-dibromoethane (4.136 g, 22 mmol). After stirring for 2 hrs, catalytic amount of TBAI (0.738 g, 2.0 mmol) was added and the mixture was continued to stir at room temperature for 8 hrs. The reaction mixture was filtered and the solid was washed with diethyl ether 3 times. The filtrate was diluted with water (200 mL) and extracted with diethyl ether (75 mL*4). The combined organic phases were washed with 70 mL of brine, dried over Na2SO4 and concentrated in vacuo. The residue was chromatographed with a short alumina column (1: 10 (v/v) EtOAc / n-hexane) to afford the desired compound as yellow oil (3.3 g, 88.7 %). 1H NMR (400MHz, CDCl3): delta 1.27 (m, J=6.8Hz, 6H), 1.42 (m, 4H), 4.18 (m, 4H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 105-53-3, its application will become more common.

Reference:
Patent; Sunshine Lake Pharma Co., Ltd.; Xi, Ning; XI, Ning; (152 pag.)EP2408300; (2016); B1;,
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369-26-6, Adding some certain compound to certain chemical reactions, such as: 369-26-6, name is Methyl 3-amino-4-fluorobenzoate, 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 369-26-6.

To a solution of methyl 3-amino-4-fluorobenzoate (100 mg, 0.591 mmol) in DCM (3 ml) was added 4-(l-methylethyl)benzoyl chloride (162 mg, 0.887 mmol) and pyridine (96 mu, 1.18 mmol) at room temperature. The mixture was stirred for 1 h. 1 M HC1 and DCM were added and the phases were separated, the organic phase collected and the volatiles were removed in vacuo. The compound was purified by flash column chromatography. Yield: 135 mg (72percent); white solid. MS (ESI+) m/z 316 [M+H]+. HPLC purity: 99percent.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 369-26-6.

Reference:
Patent; KANCERA AB; HAMMER, Kristin; JOeNSSON, Mattias; KRUeGER, Lars; (230 pag.)WO2017/108282; (2017); A1;,
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56525-63-4, Name is Methyl 3-chloro-4-methylbenzoate, 56525-63-4, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows.

(2-Chloro-4-(methoxycarbonyl)benzyl)triphenylphosphonium bromideMethyl 3-chloro-4-methylbenzoate (2.20 g, 11.96 mmol) was dissolved in carbon tetrachloride (30 mL) and N-bromosuccinimide (2.10 g, 11.80 mmol) was added followed by a catalytic amount of benzoyl peroxide (25 mg). The reaction mixture was refluxed for 6h. (ca. 90% conversion). After cooling to room temperature, a precipitate was filtered. The filtrate was concentrated to give crude brominated intermediate (3.20 g), which was used for the next step without further purification.

Statistics shows that Methyl 3-chloro-4-methylbenzoate is playing an increasingly important role. we look forward to future research findings about 56525-63-4.

Reference:
Patent; REPLIGEN CORPORATION; JACQUES, Vincent; RUSCHE, James R.; PEET, Norton P.; SINGH, Jasbir; WO2012/118782; (2012); A1;,
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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 701-83-7 as follows. 701-83-7

To 122 g (0.79 mol) of 3-fluorophenylacetate was added Aids (137 g, 1.03 mol) and theresulting mixture was heated at 160 C for 1.5 h then cooled at 0 C. HC1 IN was carefully addedfollowed by Et2O. The aqueous phase was extracted(2X) with Et2O and the combined organic phasewashed with brine, dried over Na2SO4 and evaporated to give the title compound.

According to the analysis of related databases, 701-83-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK FROSST CANADA & CO.; WO2004/108720; (2004); A1;,
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These common heterocyclic compound, 4897-84-1, name is Methyl 4-bromobutanoate, 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. 4897-84-1

STEP B: methyl 4- (nitrooxy) butanoateMethyl 4-bromobutanoate (6.0 g; 33 mmol) was dissolved in C3/4CN (120 mL) and silver nitrate (14.0 g, 82.6 mmol) was added. The reaction was heated at 80¡ãC in the dark for 4 hours. Solvent was evaporated and the crude was dissolved in EtOAc (80 ml) .Precipitate was filtered off and organic phase was washed with water (2 x 100 ml) and brine (1 x 100 ml), dried over Na2SC>4 and concentrated affording the title compound as an oil. (5.0 g, 93percent)1H-NMR (CDC13) : 4.54 (2H,t J=6.31); 3.73 (3H,s); 2.48 (2H,t J=7.15) ; 2.08 (2H,m) .

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 4897-84-1.

Reference:
Patent; NICOX S.A.; ALMIRANTE, Nicoletta; IMPAGNATIELLO, Francesco; NICOTRA, Alessia; MANDELLI, Valentino; BRAMBILLA, stefania; WO2011/101245; (2011); A1;,
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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. 455-68-5, name is Methyl 3-fluorobenzoate, This compound has unique chemical properties. The synthetic route is as follows., 455-68-5

General procedure: Compounds 6a-t were synthesized from substituted benzoic acid via six steps according to the literature method as described. Various substituted benzoic acids 1a-t were treated with SOCl2 to give compounds 2a-t, which were reacted with CH3OH and EtN3 in CH2Cl2 at 0 to afford compounds 3a-t. Compounds 4a-t were prepared by the reaction of compounds 3a-t, hydrazine hydrate in CH3OH under reflux condition about 5h. Subsequently, compounds 5a-t were obtained by reaction of compounds 4a-t with CS2 and KOH in CH3OH. Compounds 6a-t were obtained by the cyclization reaction of compounds 5a-t in the presence of HCl at 0-5¡ãC.

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Reference:
Article; Li, Liangjing; Ding, Hao; Wang, Baogang; Yu, Shichong; Zou, Yan; Chai, Xiaoyun; Wu, Qiuye; Bioorganic and Medicinal Chemistry Letters; vol. 24; 1; (2014); p. 192 – 194;,
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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. 90030-48-1, name is Sodium 3-methoxy-3-oxopropane-1-sulfinate, A new synthetic method of this compound is introduced below., 90030-48-1

Cu(I)I (570 mg, 3.02 mmol) was added to a solution of 4-((8-(6-bromo-4- methylbenzo[d]thiazol-2-yl)-8-azabicyclo[3.2.l]octan-3-yloxy)methyl)-5-cyclopropyl-3-(2- (trifluoromethoxy)phenyl)isoxazole_(960 mg, 1.51 mmol), sodium 3-methoxy-3-oxopropane- 1-sulfinate (790 mg, 4.54 mmol ) and L-proline (174 mg, 1.51 mmol) in dimethylsulfoxide (20 ml) at room temperature and the resulting mixture warmed to 130 C. After 16 h, water and ethyl acetate were added and the mixture filtered through celite. The filtrate was then washed with cold water, brine, dried over anhydrous Na2S04, filtered, concentrated under reduced pressure and purified by flash column chromatography using silica gel 100-200 mesh, eluting with 0-65% ethyl acetate in petroleum ether to afford the titled compound (0.25 g, 25 %) as a solid. LC-MS: 2.57 mins, [M+H]+ 706

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; INORBIT THERAPEUTICS AB; SHARMA, Rajiv; BENTHEM, Lambertus; JUDKINS, Robert; (69 pag.)WO2020/33382; (2020); A1;,
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58101-60-3, The chemical industry reduces the impact on the environment during synthesis 58101-60-3, name is Methyl 3-cyclopentenecarboxylate, I believe this compound will play a more active role in future production and life.

EXAMPLE 39 (+-) Methyl 3-Butyl-4,5,6,6a-tetrahydro-3aH-cyclopenta[d]isoxazole-5-carboxylate (45, Scheme 9, Ester Group and Isooxazoline Ring are cis to Each Other), and (+-) Methyl 3-Butyl-4,5,6,6a-tetrahydro-3aH-cyclopenta[d]isoxazole-5-carboxylate. (46, Scheme 9, Ester Group and Isooxazoline Ring are trans to Each Other) To a refluxing solution of methyl 3-cyclopenten-1-carboxylate 43 (10.21 g, 80.9 mmol) and phenyl isocyanate (17.5 mL, 161 mmol) in dry benzene (50 mL) was added dropwise, a mixture of 1-nitropentane (10.8 mL, 87.8 mmol) and Et3N (20 drops) in dry benzene (30 mL) over a period of 1 h. The mixture was heated at reflux for an additional hour. The solids were removed by filtration, and washed with Et2O. The combined filtrate was concentrated to yield orange oil, which was purified by flash chromatography (silica gel, 0 to 50% ethyl acetate in hexanes).

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

Reference:
Patent; BioCryst Pharmaceuticals, Inc.; US6562861; (2003); B1;,
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