Author: Jessica.F

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. 1150566-27-0, name is Ethyl 6-chloroimidazo[1,2-b]pyridazine-3-carboxylate, A new synthetic method of this compound is introduced below., Application In Synthesis of Ethyl 6-chloroimidazo[1,2-b]pyridazine-3-carboxylate

A 500 ml one-necked flask was charged with ethyl 6-chloroimidazo [1,2-b] pyridazine-3-carboxylate (11.28 g, 50 mmol)And methanol 50ml,Sodium hydroxide (4.0 g, 100 mmol)Dissolved in 100ml of water,Added to the reaction flask,The reaction was completed at 25 C for 4 hours. The reaction was completed by TLC and neutralized with 30% hydrochloric acid until pH = 4. The mixture was suction filtered, the filter cake was washed with a small amount of water,Dry to give 6-chloroimidazo [1,2-b] pyridazine-3-carboxylic acid purity, yield 91%.

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; Shandong Youbang Biochemical Technology Co., Ltd.; Tan Pingzhong; Geng Xuanping; Cheng Wei; Lai Xinsheng; Lai Chao; Lai Ziteng; (7 pag.)CN106831782; (2017); A;,
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Related Products of 27492-84-8,Some common heterocyclic compound, 27492-84-8, name is Methyl 4-amino-2-methoxybenzoate, molecular formula is C9H11NO3, 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 2-methoxy-4-aminobenzoate (10g, 55.25mmol) and hydroxylamine hydrochloride (15.36g, 221mmol) were taken up in MeOH (80ml) and a solution of KOH (15.4g, 275mmol) in MeOH (55ml) was added carefully. The resultant mixture was stirred at reflux for 36hrs. The volatiles were removed in vacuo. The residue was taken up in 1 M NaOH (50ml) and washed with ethyl acetate (EtOAc, 50ml). Concentrated HCl was added slowly until precipitation of a solid (pH was 10). The solid was filtered off, washed with H2O, then methyl-tert-butyl ether (MTBE) and dried under vacuum. 1H NMR showed the solid contained approx. 1/3 molar equivalent of ethyl acetate. The solid was taken up in 1M NaOH (100ml) and the EtOAc was removed in vacuo. Concentrated HCl was added carefully until precipitation of a solid (pH was 8). The solid was collected by filtration, washed with H2O, then MTBE and dried under vacuum to give 4.67g (47%) of the title compound as a dark red solid.1H NMR (delta, 250MHz, d6-DMSO): 3.75 (s, 3-H, OMe), 5.64 (s, 2-H, NH2), 6.14 (dd, 1-H, aromatic), 6.18 (brs, 1-H, aromatic), 7.48 (d, 1-H, aromatic), 8.73 (s, 1-H, NH), 10.06 (s, 1-H, OH).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 4-amino-2-methoxybenzoate, its application will become more common.

Reference:
Patent; Nogra Pharma Limited; NACCARI, Giancarlo; BARONI, Sergio; EP1910275; (2013); B1;,
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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. 6642-30-4, name is Methyl methylcarbamate, This compound has unique chemical properties. The synthetic route is as follows., Formula: C3H7NO2

EXAMPLE 10 2-SEC BUTYLPHENYL N-METHYLCARBAMATE To a mixture of methyl N-methylcarbamate (0.89 g, 0.01 mole) and 2-sec butylphenol (1.5 g, 0.01 mole) in dichloroethane (10 ml), a solution of phosphorus tribromide (2.7 g, 0.01 mole) in dichloro-ethane (6 ml) was added and the mixture was refluxed for eight hours. It was then worked up and purified as described earlier to give 2-sec butylphenyl N-methylcarbamate.

According to the analysis of related databases, 6642-30-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Council of Scientific and, Industrial Research; EP446514; (1991); A1;,
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Adding a certain compound to certain chemical reactions, such as: 41841-16-1, name is Methyl 2-(4-bromophenyl)acetate, 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 41841-16-1, Product Details of 41841-16-1

At 40 C., a solution of intermediate B.i (52 g) in THF (100 mL) was carefully added over a period of 40 min to a suspension of NaH (15.6 g) in dry THF (450 mL). Stirring was continued for 70 min without heating and the temperature dropped to 27 C. The evolution of gas stopped before dimethylcarbonate (76.42 mL) was added dropwise while the temperature of the mixture was maintained at 29-31 C. Stirring was continued for 22 h at rt. The mixture was cooled to -10 C. and then carefully neutralized to pH 6-7 with aq. HCl before bulk of the THF was removed in vacuo. The residue was dissolved in EA (700 mL), washed 3 times with 1 N aq. HCl-solution and once with brine, dried over MgSO4. Most of the EA was evaporated before Hex was added. The product crystallised overnight at 4 C. The crystals were collected, washed with Hex and dried to give the expected product as pale yellow crystals (45.9 g).1H-NMR (D6-DMSO): delta 3.66 (s, 6H); 5.07 (s, 1H); 7.30-7.34 (m, 2H); 7.55-7.59 (m, 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; Bolli, Martin; Boss, Christoph; Treiber, Alexander; US2012/142716; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 79669-50-4, name is methyl 5-bromo-2-methyl-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 79669-50-4, Recommanded Product: methyl 5-bromo-2-methyl-benzoate

5-Bromo-2-methylphenyl)methanolTo a solution of methyl 5-bromo-2-methylbenzoate (108 g, 471 mmol) in THF (1600 mL) was added LiAIH4(21.47 g, 566 mmol) slowly under nitrogen at 0 C. The resulting mixture was stirred at 0 C for 1 hr. Then 3.73 mL of water was added to the reaction mixture, followed by 3.75 mL of 10% NaOH, and 1 1.19 mL of water, filtered and concentrated to afford the title compound (5-bromo-2-methylphenyl)methanol (88 g, 416 mmol, 88 % yield). LC-MS MS m/z 185.1 (M-OH)+, 1.59 (ret. time)

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 5-bromo-2-methyl-benzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ASTEX THERAPEUTICS LIMITED; BOEHM, Jeffrey Charles; DAVIES, Thomas Glanmor; WOOLFORD, Alison Jo-anne; GRIFFITHS-JONES, Charlotte Mary; WILLEMS, Hendrika Maria Gerarda; NORTON, David; SAXTY, Gordon; HEIGHTMAN, Thomas Daniel; LI, Tindy; KERNS, Jeffrey K.; DAVIS, Roderick S.; YAN, Hongxing; WO2015/92713; (2015); 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. 39622-80-5, name is Dimethyl 2-bromoisophthalate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 39622-80-5

Diagram 2. Synthesis of Naproxen C0 (compound 9). Reactants and conditions: i/KMnO4 (2.0 equiv.), tBuOH/H2O (1/1), reflux, 4 hrs, then KMnO4 (2.0 equiv.), reflux, 16 hrs; ii/ MeOH, conc. H2SO4, reflux, 16 hrs; iii/ dimethyl 2-bromoisophthalate 6 (0.92 equiv.), Pd(PPh3)4 (0.03 equiv.), aq. Na2CO3 (4.2 equiv., 2 M), DME/EtOH, reflux, 16 hrs; iv/ aq. LiOH (7.2 equiv., 1 M), THF, reflux, 4 hrs.

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 39622-80-5.

Reference:
Patent; Institut National de la Recherche Agronimique; Slama Schwok, Anny; Delmas, Bernard; Quideau, Stephane; Bertrand, Helene; Tarus, Bogdan; US2014/163107; (2014); A1;,
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Related Products of 344-14-9, 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. 344-14-9, name is Dimethyl 2-fluoromalonate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

First, put a stirrer in a 35 mL sealed tube, and then add 2-methyl-1-butene-3-yne (32 muL, 0.33 mmol), 0.9 mL tetrahydrofuran (0.9 mL), and 2-chloroacetamido Quinoline (66.2mg, 0.3mmol), dimethyl 2-fluoromalonate (70.4mg, 0.45mmol), to this mixed solution were added CuI (5.7mg, 0.03mmol) and Cs2CO3 (117.3mg, 0.36mmol), charge N2 for 3 minutes with a glass tube connected to nitrogen, fully drive out the air, seal the nozzle with a cock, and stir the reaction at 800C for 1.5 hours. After the reaction is completed, the system is cooled to room temperature and added to the reaction system. 2ml of distilled water was extracted with ethyl acetate. The organic phases were combined, and the solvent of the organic phase was distilled off under reduced pressure. 84.1 mg of product 4e was separated by silica gel column chromatography. The yield was 70%.

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

Reference:
Patent; Anyang Normal University; Lv Yunhe; Pu Weiya; Wang Xin; Wang Xiaoxing; (15 pag.)CN110627718; (2019); A;,
Ester – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 344-14-9, name is Dimethyl 2-fluoromalonate, 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 344-14-9, Product Details of 344-14-9

Part A: 5-Fluoro-6-hydroxy-2,4(1H,3H)-pyrimidinedione. A mechanically stirred solution of urea (60.06 g, 1 mol) and dimethyl fluoromalonate (150.1 1 g, 1 mol) in methanol (1 L) was treated with 25 wt% NaOMe in methanol (-4.6M, 435 mL, 2 mol). The mixture was refluxed for 3 h and then allowed to cool to room temperature. The mixture was filtered, the wet cake was dissolved in warm water (-1.2L), and the resulting aqueous solution was acidified with concentrated aqueous HCI(-160 mL) to pH = 2 while stirring over 1 h. The mixture was allowed to cool to room temperature, and the product was filtered and washed thoroughly with water, then dried under vacuum to give 5-fluoro-6-hydroxy-2,4(1 H,3H)-pyrimidinedione (80 g, 55%) as a white solid. LCMS: (M+H)+: 147.0.

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, Dimethyl 2-fluoromalonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2009/61879; (2009); A1;,
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Synthetic Route of 18595-12-5, These common heterocyclic compound, 18595-12-5, name is Methyl 5-amino-2-methylbenzoate, 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 Preparation of 1-[1-(2-toluoylmethyl)-2-oxo-5-pivaloyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl]-3-(3-methoxycarbonyl-4-methylphenyl)urea Methyl 5-amino-2-methylbenzoate (223 mg) was dissolved in tetrahydrofuran (30 ml), under ice-cooling triphosgene (135 mg) was added, triethylamine (116 mul) was added thereto five times every 3 minutes, the mixture was stirred for 10 minutes at same temperature. Subsequently, a solution of 1-(2-toluoylmethyl)-2-oxo-3-amino-5-pivaloyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (500 mg) in tetrahydrofuran (20 ml) was added dropwise, stirred for 30 minutes at same temperature, and then stirred for 3 hours at room temperature. The reaction mixture was concentrated under reduced pressure, water (50 ml) was added, and extracted with methylene chloride. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography(chloroform:ethyl acetate=10:1), to thereby obtain 271 mg of the titled compound. 1H-NMR(CDCl3) delta: 1.04(9H, s), 2.39(3H, s), 2.50(3H, s), 2.52(3H, s), 3.83(3H, s), 3.96(1H, dd), 4.34(1H, t), 4.43(1H, d), 4.79-4.89(1H, m), 5.50(1H, d), 6.01(1H, d), 6.89(1H, brs), 7.03(1H, s), 7.03-7.35(6H, m), 7.43(1H, t), 7.69(1H, d), 7.88(1H, d)

Statistics shows that Methyl 5-amino-2-methylbenzoate is playing an increasingly important role. we look forward to future research findings about 18595-12-5.

Reference:
Patent; Zeria Pharmaceutical Co., Ltd.; US6239131; (2001); B1;,
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Application of 849758-12-9, A common heterocyclic compound, 849758-12-9, name is Methyl 4-bromo-3-fluorobenzoate, molecular formula is C8H6BrFO2, 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 methyl 4-bromo-3-fluorobenzoate (526 mg, 2.26 mmol) in dioxane (10 mL) and H20 (2 mL) were added tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2- dioxaborolan-2-yl)- 1H-pyrazole- 1 -carboxylate (797 mg, 2.71 mmol), K3P04 (958 mg, 4.51 mmol) and XPhos-G2-Pd-preCat (35.5 mg, 0.045 mmol) at rt. The reaction was stirred under N2 at 60 C overnight. The reaction mixture was diluted with EtOAc,washed with H20 and brine. The organic phase was dried over Na2SO4, filtered and concentrated. The crude product was purified by normal phase chromatography to give two products as white solids. Intermediate 151A (463 mg, 64%): ?H NMR (400MHz, CDC13) oe 8.51 (d,J=1.5 Hz, 1H), 8.10 (s, 1H), 7.84 (dd,J=8.1, 1.5 Hz, 1H), 7.79 (dd, J=11.4, 1.5 Hz, 1H), 7.63 (t,J=7.8 Hz, 1H), 3.92 (s, 3H), 1.68 (s, 9H). LC-MS(ESI) m/z:321.0 [M+H]. Intermediate 151B (175 mg, 35%): ?H NMR (400MHz, CDC13)oe 8.06(d, J=1.8 Hz, 2H), 7.85 (dd,J=8.1, 1.8 Hz, 1H), 7.80 (dd,J11.7, 1.5 Hz, 1H), 7.66 (t,J7.7 Hz, 1H), 3.94 (s, 3H). LC-MS(ESI) m/z: 221.0 [M+H].

The synthetic route of 849758-12-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; LADZIATA, Vladimir; GLUNZ, Peter W.; HU, Zilun; WANG, Yufeng; (0 pag.)WO2016/10950; (2016); A1;,
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