Tag: M.W=100-200

Related Products of 174403-69-1, 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. 174403-69-1, name is Methyl 4-fluoro-2-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of pyrazole (100 mg, 1.47 mmol), methyl 4-fluoro-2-methylbenzoate (123.51 mg, 0.73 mmol) and potassium carbonate (609.0 mg, 4.41 mmol) in N,N-dimethylformamide (5 mL) was stirred at 60 C for 16 h. The reaction was poured into water (5 mL) and extracted with EtOAc (20 mL). The organic extract was washed with water (20 mL x 2) and brine (10 mL), dried over Mg504 and concentrated. The residue was purified by prep-TLC (33% ethyl acetate in petroleum ether, Rf = 0.3) to afford methyl 2-methyl-4-(1H-pyrazol-1-yl)benzoate (50 mg, 15.7% yield) as a white solid. LCMS (Method 5-95AB): tR =0.732 mi [M + Hj = 216.9.

The chemical industry reduces the impact on the environment during synthesis Methyl 4-fluoro-2-methylbenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; RQX PHARMACEUTICALS, INC.; GENENTECH, INC.; CHEN, Yongsheng; SMITH, Peter Andrew; ROBERTS, Tucker Curran; HIGUCHI, Robert I.; PARASELLI, Prasuna; KOEHLER, Michael F. T.; SCHWARZ, Jacob Bradley; CRAWFORD, James John; LY, Cuong Q.; HANAN, Emily J.; HU, Huiyong; YU, Zhiyong; (424 pag.)WO2017/84630; (2017); A1;,
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These common heterocyclic compound, 108928-00-3, name is Ethyl 2,4-difluorobenzoate, 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. COA of Formula: C9H8F2O2

2,4-Difluorobenzoic acid ethyl ester (5.33g) was cooled to 0C and treated with concentrated sulfuric acid (3. 5mL) and then fuming nitric acid (3. 5mL). The mixture was stirred for 2 hours at 0C and then partitioned between dichloromethane (2x50mL) and water (25mL). The organic phase was back extracted with water (25mL) and then dried over magnesium sulfate and concentrated in vacuo. This provided the desired compound as a white solid (5. 00g) which was used without further purification.

The synthetic route of Ethyl 2,4-difluorobenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM P.L.C.; WO2003/87098; (2003); 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. 1260092-46-3, name is tert-Butyl 3-(2-aminoethoxy)propanoate, A new synthetic method of this compound is introduced below., name: tert-Butyl 3-(2-aminoethoxy)propanoate

To a solution of fert-butyl 3-(2-aminoethoxy)propanoate (246 mg, 1.302 mmol) in DMF (1.5 ml) at rt was added bis(2,5-dioxopyrrolidin-l-yl) 3,3′-oxydipropanoate (232 mg, 0.651 mmol) and followed DIPEA (0.284 ml, 1.628 mmol). The mixture was allowed to stir at rt over night and concentrated to dryness. To the resulting residure at 0 C was added 1.0 mL neat TFA, and the resulting mixture was allowed to stir at rt overnight. The mixture was concentrated to give the crude product, which was used without further purification. UPLC-MS Method A: TR = 0.7 min, m/z = 393 (z = 1).

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; MERCK SHARP & DOHME CORP.; LIN, Songnian; YAN, Lin; HUO, Pei; PISSARNITSKI, Dmitri; FENG, Danqing; NARGUND, Ravi; MADSEN-DUGGAN, Christina; ZHU, Yuping; KEKEC, Ahmet; WU, Zhicai; (191 pag.)WO2017/205309; (2017); 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. 13831-03-3, name is tert-Butyl propiolate, A new synthetic method of this compound is introduced below., Safety of tert-Butyl propiolate

To the mixture of methyl 3-iodobenzoate (157 mg, 0.60 mmol), potassium carbonate (166mg, 1.20 mmol), cupper(I) iodide (14 mg, 0.07 mmol) and PdC12(Ph3P)2 (21 mg, 0.03 mmol) in tetrahydroffiran (2 mE) was added tert-butyl propiolate (330 pL, 2.40 mmol) at room temperature. Afier stirred for 20 h at 60 C., the mixture was evaporated to dryness. Theresidue was chromatographed on a silica gel (EtOAc:hex- anes=0: 1 -1 :10) to give the title compound 9-1(155 mg, 99%yield) as a light brown oil.?H NMR (300 MHz, CDC13) oe 8.25 (t, J=1.4, 1H), 8.16- 8.05 (m, 1H), 7.80-7.68 (m, 1H), 7.46 (t, J=7.8, 1H), 3.93 (s,3H), 1.55 (s, 9H).

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; The Broad Institute, Inc.; Massachusetts General Hospital; Hung, Deborah; Stanley, Sarah; Kawate, Tomohiko; Iwase, Noriakie; Shimizu, Motohisa; (32 pag.)US9416121; (2016); B2;,
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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, Computed Properties of C7H13NO2

A mixture of 2,4-dichloro-5-fluoro-3-nitrobenzoic acid (10.2 g, 40 mmol) and thionyl chloride (19.0 g, 160 mmol) in dry benzene (120 ml) was refluxed for 3 – 4 h under anhydrous conditions. The solvent and excess thionyl chloride were then distilled off under reduced pressure, and dry benzene (20 ml) was then introduced into the reaction vessel and re-distilled so as to remove traces of thionyl chloride. The resulting 2,4-dichloro-5-fluoro-3-nitrobenzoyl chloride, formed as thick oil, was used as such for the next step without further purification. To a stirred and cooled (5-10 C) solution of ethyl 3-(N,N-dimethylamino)acrylate (6.3 g, 44 mmol) and triethylamine (8.1 g, 80 mmol) in dry benzene (50 ml) was added dropwise a solution of the crude acid chloride (prepared above) in dry benzene (25 ml). The resulting mixture was refluxed for 2 h, then cooled to rt and washed with water (2 x 30 ml). The organic layer was separated, dried (anhydrous MgSO4) and the solvent benzene was then evaporated to dryness under reduced pressure. The residual product was soaked in methanol (10 ml) whereby the title compound 5 was produced as yellowish powder which was collected by suction filtration and dried. Yield = 13.8 g (91%). IR (KBr): v 3074, 3037, 2988, 2928, 2873, 1689, 1619, 1554, 1454, 1397, 1375, 1344, 1321, 1278, 1206, 1177, 1129, 1030 cm-1; 1H NMR (300 MHz, CDCl3): delta 0.95 (t, J = 7.1 Hz, 3H, CH3), 2.97 (s, 3H) and 3.37 (s, 3H) [N (CH3)2], 3.94 (q, J = 7.1 Hz, 2H, CH2Me), 7.27 (d, 3JH-F = 8.2 Hz, 1H, H-6), 7.91 (br s, 1 H, N-C(3″)-H); 13C NMR (75 MHz, CDCl3): delta 13.8 (CH3CH2), 43.3, 48.4 [N (CH3)2], 60.2 (CH2Me), 100.9 (C-2″), 114.5 (d, 2JC-F = 23.3 Hz, C-4), 116.9 (d, 2JC-F = 23.1 Hz, C-6), 118.2 (d, 3JC-F = 4.5 Hz, C-1), 144.2 (d, 3JC-F = 6 Hz, C-3), 148.8 (br d, 4JC-F = 1.3 Hz, C-2), 156.6 (d, 1JC-F = 254 Hz, C-5), 160.5 (N-C-3″), 166.5 (CO2Et), 185.1 (C = O).

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, Ethyl 3-(dimethylamino)acrylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Universitaet Duisburg-Essen; EP2128160; (2009); A1;,
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Related Products of 37746-78-4, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 37746-78-4 name is (E)-Ethyl 4-bromobut-2-enoate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: To a vigorously stirring solution of alpha-imino ester 1 (0.5 mmol,1 equiv) and E-ethyl-4-bromocrotonate or methyl-4-bromocrotonate (2, 1.5 mmol, 3 equiv) in EtOH (2 mL) was added indium powder (1 mmol, 2 equiv). The mixture was allowed to stir vigorously for 6 h at 30 C. After this period, the reaction mixturewas quenched with 2 mL of water and transferred to a separating funnel and extracted using ethyl acetate (315 mL). The combined organic layers were dried over anhydrous Na2SO4. Then the solvent was evaporated under vacuum. Purification of the resulting crude reaction mixture by column chromatography on silica gel (EtOAc/Hexane as eluent) gave the product 3 (see Tables 1 and 2 and Scheme 2 for individual entries).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (E)-Ethyl 4-bromobut-2-enoate, and friends who are interested can also refer to it.

Reference:
Article; Aslam, Nayyar Ahmad; Babu, Srinivasarao Arulananda; Sudha, Arya Jayadev; Yasuda, Makoto; Baba, Akio; Tetrahedron; vol. 69; 32; (2013); p. 6598 – 6611;,
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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. 217314-47-1, name is Methyl 3-amino-5-methoxybenzoate, A new synthetic method of this compound is introduced below., Recommanded Product: 217314-47-1

To the solution of 1.57 g (8.7 mmol, 1 eq) 3-amino-5-methoxy-benzoic acid methyl ester (CAS 217314-47-1, can be prepared according to literature procedures) and 0.11 g (0.87 mmol, 0.1 eq) 4-dimethylaminopyridine in 18 ml THF is added the solution of 1.89 g (8.7 mmol, 1 eq) BOC-anhydride in 7 ml THF. The reaction mixture is stirred at rt over night. After dilution with EtOAc the mixture is washed with aqueous sodium bicarbonate and brine, dried over sodium sulfate, and the solvents are evaporated at reduced pressure. The residue is purified by chromatography on silica (flashmaster, hexane to hexane/EtOAc 7/3) to give 0.83 g (2.9 mmol, 34%) product as white solid.MS (LC/MS): 182=[M+H]+ 1H-NMR (400 MHz, CDCl3): 7.54-7.51 (m, 1H), 7.39 (br s, 1H), 7.29-7.28 (m, 1H), 6.59 (br s, 1H), 3.93 (s, 3H), 3.87 (s, 3H), 1.56 (s, 9H).

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; Betschart, Claudia; Lerchner, Andreas; Machauer, Rainer; Rueger, Heinrich; Tintelnot-Blomley, Marina; Veenstra, Siem Jacob; US2008/132477; (2008); A1;,
Ester – Wikipedia,
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Reference of 114312-57-1, A common heterocyclic compound, 114312-57-1, name is Ethyl 3-fluoro-2-methylbenzoate, molecular formula is C10H11FO2, 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.

Add ethyl 3-fluoro-2-methylbenzoate (5.1g, 28mmol) to the reaction flask,N-bromosuccinimide (5.6g, 31mmol),Benzoyl peroxide (0.34g, 1.4mmol) and CCl4 (30mL).Under the protection of nitrogen, the temperature of the reaction solution was raised to 82C and the reaction was stirred for 17 hours.After the reaction was completed, the reaction solution was cooled to room temperature, filtered, and the filter cake was washed with EtOAc (50 mL). The resulting filtrate was sequentially saturated sodium thiosulfate solution (100 mL×2),The citric acid solution (50 mL) and saturated brine (50 mL) were washed, dried over anhydrous sodium sulfate, filtered, and the filtrate was vortexed under reduced pressure.The obtained crude product was purified using silica gel column chromatography (eluent: PE/EA (v/v) = 10/1),The title compound was obtained as a light yellow oil (6.17g, 84%).

The synthetic route of 114312-57-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Luo Huichao; Ren Qingyun; Yin Junjun; Wu Chunlin; Fan Yuxin; Mo Yufeng; Zhang Yingjun; (102 pag.)CN111057074; (2020); A;,
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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. 685-88-1, name is Diethyl fluoromalonate, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of Diethyl fluoromalonate

To a solution of diethyl 2- fluoromalonate (5.00 g, 28.1 mmol) in EtOH (100 mL) was added LiOH H20 (2.70 g, 64.3 mmol) at 25 C. The mixture was heated to 50 C for 16 hours. The mixture was filtered to collect solid. The filtrate was concentrated to dryness to get oil. The oil and the solid were dissolved in H20 (30 mL) and MTBE (100 mL), the mixture was acidified by adding cone. HC1 to pH 1, the aqueous layer was extracted with MTBE (30 mL x2), the combined organic layers were dried over Na2S04, filtered and concentrated to give 2-fluoromalonic acid (3.00 g, yield 88%) as a solid.

According to the analysis of related databases, 685-88-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; N30 PHARMACEUTICALS, LLC; SUN, Xicheng; QIU, Jian; STOUT, Adam; WO2012/83165; (2012); 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. 18595-18-1, name is Methyl 3-amino-4-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of Methyl 3-amino-4-methylbenzoate

Step 1. Preparation of methyl 1H-indazole-6-carboxylate (i-14b).Methyl 3-amino-4-methylbenzoate (i-14a) (5.0 g, 30.2 mmol) was dissolved in AcOH (140 mL). Sodium nitrite (2.1 g, 30.2 mmol) in water (3.5 mL) was added dropwise to the solution of starting material under ice-cooling at room temperature. The ice bath was removed and themixture was stirred overnight. Half of the solvent was evaporated, the mixture was diluted with water (80 mL) and extracted with EtOAc (3×30 mL). The collected organic phase was washed with water and brine (2×200 mL), dried and evaporated to afford the title compound (4.4 g), yield 83%. LCMS (ESI): calc?d for C9H8N202, [M+H]: 177, found: 177.

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 18595-18-1.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BARR, Kenneth Jay; MACLEAN, John; ZHANG, Hongjun; BERESIS, Richard Thomas; WO2014/28600; (2014); A2;,
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