Day: August 5, 2021

Adding a certain compound to certain chemical reactions, such as: 16135-36-7, Methyl 4-aminonicotinate, 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, Safety of Methyl 4-aminonicotinate, blongs to pyridine-derivatives compound. Safety of Methyl 4-aminonicotinate

TBTU (1.99 g, 6.19 mmol) was added to a stirred solution of 2′-ethoxy-biphenyl-4-carboxylic acid (1.00 g, 4.13 mmol) and triethylamine (1.73 mL, 12.4 mmol) in dichloromethane (50 mL). After 2 min, 4-amino-nicotinic acid methyl ester (628 mg, 4.13 mmol) was added, and the mixture was heated to reflux for 1 d then allowed to stand at rt for another 2 d. After washing with 1 M aq NaOH (25 mL), water (25 mL) and brine (25 mL the solution was concentrated under reduced pressure. The residue was purified by flash chromatography (silica, 100% DCM to 97:3 DCM/MeOH). Yield 1359 mg (87%). HR-MS (m/z): C22 H20 N2 O4, calcd [M+H]+, 377.1501, found 377.1509.1H NMR (500 MHz, CDCl3) delta 12.21 (s, 1H), 9.24 (s, 1H), 8.93 (d, J = 5.7 Hz, 1H), 8.67 (d, J = 5.4 Hz, 1H), 8.08 (d, J = 8.5 Hz, 2H), 7.76 (d, J = 8.5 Hz, 2H), 7.39 – 7.33 (m, 2H), 7.06 (td, J = 7.5, 0.9 Hz, 1H), 7.01 (d, J = 8.1 Hz, 1H), 4.08 (q, J = 7.0 Hz, 2H), 4.05 (s, 3H), 1.37 (t, J = 7.0 Hz, 3H).

The synthetic route of 16135-36-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bauer, Udo; Giordanetto, Fabrizio; Bauer, Martin; O’Mahony, Gavin; Johansson, Kjell E.; Knecht, Wolfgang; Hartleib-Geschwindner, Judith; Carlsson, Eva Toeppner; Enroth, Cristofer; Bioorganic and Medicinal Chemistry Letters; vol. 22; 5; (2012); p. 1944 – 1948;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.6443-85-2, name is 2-(Pyridin-3-yl)acetonitrile, molecular formula is C7H6N2, molecular weight is 118.14, as common compound, the synthetic route is as follows.Formula: C7H6N2

54.1 Synthesis of 3-cyano-3-(pyridin-3-yl)-pentanedioic acid diethyl ester Prepare by the method of example 1.1.2 using pyridin-3-yl-acetonitrile (0.161 mol) and ethyl bromoacetate (0.325 mol). Chromatograph on silica gel to give the title compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6443-85-2, 2-(Pyridin-3-yl)acetonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Merrell Pharmaceuticals Inc.; US5635510; (1997); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 119308-57-5 ,Some common heterocyclic compound, 119308-57-5, molecular formula is C7H5Br2NO2, 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 2,6 -dibromoisonicotinate (1 0.0 g, 33.91 mmol) in ethanol (200.0 ml) was slowly added NaBH 4 (6.4 g, 169.18 mmol) at room temperature under stirring. The reaction was heated to reflux and kept at reflux for 2 hours. The reaction solution was cooled to room temperature, and 2 M HCl ( 35.0 ml) was added slowly with stirring until the bubbling stopped. The ethanol was removed by rotary evaporation. Solid NaOH was added under stirring until the solution became basic. The solution continued to be stirred, and during stirring the product was precipitated. A white solid product was collected by filtration. After drying, the product was obtained in an amount of 5.Og (55.6%). 1H NMR (CDCl3): delta 7.44 (s, 2H, HPy), 4.70 (s, 2 H, OCH2). 13C NMR (CDCl3): delta155.05, 140.70, 124.15, 62.22. MS (EI) m/z (%): 266.8 (100%) [M +].

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. 119308-57-5, Methyl 2,6-dibromoisonicotinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Georgia Tech Research Corporation; SOLVAY (Societe Anonyme); WO2009/80799; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 54903-50-3, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 54903-50-3, name is 4,5,6,7-Tetrahydrothieno[3,2-c]pyridine. This compound has unique chemical properties. The synthetic route is as follows.

Adamantan-l-yI-(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)-methanone (STX1721, XDS04025);To a solution of 1-adamantanecarbonyl chloride (lOOmg, 0.50 mmol, 1.06 eq.) in DCM (5 mL) was added triethylamine (0.15 mL), followed by the 4,5,6,7-Tetrahydrothieno[3,2- c]pyridine (155mg, purity unknown). The reaction mixture was stirred at ambient temperature under nitrogen overnight. PS-Trisamine (10-20 mg) was added. After stirred at ambient temperature for another 2h, the mixture was filtered and evaporation of the solvent gave a residue that was purified by flash chromatography (Hexane-Ethyl acetate/hexane gradient elution) to give crystalline solid (49 mg, 33 %). mp 141-143 0C; TLC single spot at Rf. 0.49 (20% ethyl acetate/hexane); 1H NMR (270 MHz3 CDCl3) delta 1.72 (6H, s, 3 x CH2), 2.02 (9H, s, 3 x CH and 3 x CH2), 2.88 (2H, t, J= 4.6 Hz5 CH2), 3.94 (2H, t, J= 4.5 Hz, CH2), 4.69 (2H, s, CH2), 6.79 (IH, d, J= 5.2 Hz, ArH) and 7.11 (IH, d, J= 5.2 Hz3 ArH); LC/MS (APCI) m/z 302 (M÷+H); HPLC tr = 3.24 min (>99 %) in 10% water-acetonitrile.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 54903-50-3, 4,5,6,7-Tetrahydrothieno[3,2-c]pyridine.

Reference:
Patent; STERIX LIMITED; WO2006/100502; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1187236-18-5, 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. 1187236-18-5, name is Ethyl 7-bromoimidazo[1,2-a]pyridine-2-carboxylate. A new synthetic method of this compound is introduced below.

To a solution of ethyl 7-bromoimidazo[l,2-a]pyridine-2-carboxylate (400 mg, 1.486 mmol) in dry THF (3 mL) at 0 0 C was added L1AIH4 (56.4 mg, 1.486 mmol) in a schlenk tube. After the mixture stirred for 16 hours at 25C, TLC indicated the reaction was completed. The mixture was diluted with saturated aqueous H4CI (20 mL) and extracted with ethyl acetate (70 mL x 3). The combined organic layers were washed with water (40 mL) and brine (50 mL), dried over anhydrous sodium sulfate, filtered and concentrated. The crude product was purified by silica gel chromatography (pet. ether/ethyl acetate) to give the title compound.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1187236-18-5, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MSD R&D (CHINA) CO., LTD.; ACTON, John, J., III; BAO, Jianming; DENG, Qiaolin; EGBERTSON, Melissa; FERGUSON, Ronald, III; GAO, Xiaolei; HARRISON, Scott Timothy; KNOWLES, Sandra, L.; LI, Chunsing; LO, Michael Man-Chu; MAZZOLA, Robert, D., Jr.; MENG, Zhaoyang; NA, Meng; RUDD, Michael, T.; SELYUTIN, Oleg, B.; TELLERS, David, M.; TONG, Ling; ZHANG, Fengqi; (195 pag.)WO2019/5587; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 17282-00-7, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.17282-00-7, name is 3-Bromo-5-methylpyridin-2-amine, molecular formula is C6H7BrN2, molecular weight is 187.04, as common compound, the synthetic route is as follows.

General procedure: Under N2 atmosphere, to a solution of palladium acetate (120 mg, 0.53 mmol, 5 mol %) and XANTPHOS (309 mg, 0.53 mmol, 5 mol %) in anisole (30 mL) was added 3-bromo-5-methyl-pyridin-2-ylamine (5) (2.0 g, 10.7 mmol, 1.0 equiv), aryl iodides (6) (10.7 mmol) and cesium carbonate (4.9 g, 15.0 mmol, 1.4 equiv), and the mixture was stirred at 130 C for 1-13 h. After cooling to room temperature, water (40 mL) was added to the mixture. The mixture was concentrated in vacuo and ethyl acetate (100 mL) was added to the residue. The organic layer was washed with water (20 mL) and concentrated in vacuo to give the crude product, which was purified by flash chromatography to give 7.

Statistics shows that 17282-00-7 is playing an increasingly important role. we look forward to future research findings about 3-Bromo-5-methylpyridin-2-amine.

Reference:
Article; Mineno, Masahiro; Sera, Misayo; Ueda, Tsuyoshi; Mizuno, Masahiro; Yamano, Mitsuhisa; Mizufune, Hideya; Zanka, Atsuhiko; Tetrahedron; vol. 70; 35; (2014); p. 5550 – 5557;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 55314-16-4, 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 55314-16-4 as follows.

Experimental Preparation of intermediates; Synthesis of 6-methyl-Nl-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-l,3-diamine 5; To 2-amino-4-nitro toluene 1 (0.033 mol) in n-butanol (29 mL) is added nitric acid (2.1 g, 65% in water) followed by cyanamide solution in water (2 mL, 0.047 mmol). The resulting mixture is heated at reflux for 25 h. After cooling to 0 0C, filtration and washing with 1 : 1 = ethanol : diethyl ether (30 mL), 2-methyl-5-nitrophenyl guanidine nitrate 2 is obtained. To 2-methyl-5-nitrophenyl guanidine 2 (0.0074 mol) in isopropanol (15 mL) is added 3 (0.0074 mol) and sodium hydroxide flakes (0.008 mol). The resulting mixture is heated at reflux for 12 h. After cooling to 0 0C, the product is collected by filtration and washed with isopropanol (6 mL) and methanol (3 mL) to afford 4. 1H NMR (400MHz, Cl6-DMSO) delta 9.31 (s, IH), 9.24 (s, IH), 8.78 (m, IH), 8.70 (m, IH), 8.61 (m, IH), 8.47 (m, IH), 7.88 (m, IH), 7.55 (m, 3H), 2.39 (s, 3H). MS (m/z) (M+l)+: 278.2

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,55314-16-4, its application will become more common.

Reference:
Patent; IRM LLC; NOVARTIS AG; LI, Xiaolin; LIU, Xiaodong; MOLTENI, Valentina; CHIANELLI, Donatella; LOREN, Jon; NABAKKA, Juliet; WO2008/137794; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 588727-65-5, 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. 588727-65-5, name is 4-(6-Bromopyridin-2-yl)benzaldehyde. A new synthetic method of this compound is introduced below.

Step 2. 4-[6-(4-Trifluoromethoxyphenyl)-pyridin-2-yl]-benzaldehyde. 4-(6-Bromo- pyridin-2-yl)-benzaldehyde (0.31 mmol), 4-trifluoromethoxyphenyl boronic acid (0.46 mmol), tetrakis(triphenylphosphine)palladium(0) (0.003 mmol), 2 M potassium carbonate (0.31 mL) and dioxane (2 mL) were combined in a vial and irradiated by microwave for 10 min at 150 0C. The reaction mixture was taken up in ether and washed with brine. The organic layer was dried over magnesium sulfate, was filtered and the solvent removed in vacuo. Purification by silica gel chromatography (EtOAc/hexanes) yielded the product (80 mg) as an off-white solid: mp 109-112 0C; 1H NMR (400 MHz, CDCl3) delta 10.11 (s, IH), 8.32 (d, J = 8.5 Hz, 2H), 8.19 (d, J = 8.1 Hz, 2H), 8.03 (d, J = 8.4 Hz, 2H), 7.89 (t, J = 7.9 Hz, IH), 7.79 (d, J = 7.7 Hz, IH), 7.74 (d, J = 8.0 Hz, IH), 7.35 (d, J = 8.3 Hz, 2H); EIMS m/z 343 (M+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,588727-65-5, 4-(6-Bromopyridin-2-yl)benzaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; DOW AGROSCIENCES LLC; LAMBERT, William; CROUSE, Gary; SPARKS, Thomas; CUDWORTH, Denise; WO2011/17513; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 866319-00-8, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 866319-00-8, name is 5-Fluoro-1H-pyrrolo[2,3-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows.

b) 5-fluoro-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde can be prepared as in Example 2 but from 545 mg of 5-fluoro-1H-pyrrolo[2,3-b]pyridine, in a mixture of 3.4 cm3 of water and 1.6 cm3 of acid acetic, and 545 mg of 1,3,5,7-tetraazatricyclo[3.3.1.1~3,7~]-decane. 265 mg of 5-fluoro-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde is obtained in the form of a beige solid with the following physical characteristics: 1H-NMR spectrum at 400 MHz: 8.15 (dd, J=3 and 9 Hz, 1H); 8.36 (dd, 1.8 and 3 Hz, 1H); 8.53 (s, 1H); 9.90 (s, 1H); 12.79 (s broad, 1H).

According to the analysis of related databases, 866319-00-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; sanofi-aventis; US2009/253679; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 17282-40-5, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 17282-40-5, name is 1-(2-Ethoxy-2-oxoethyl)pyridin-1-ium bromide. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Mixture of ethyl acetoacetate(1, 211 mg, 0.153 mmol), hydrazine (2, 81 mg, 0.153), 7-hydroxy-4-oxo-2-phenyl-4H-chromene-8-carbaldehyde (4a, 406 mg,0.153 mmol), 1-(2-ethoxy-2-oxoethyl)pyridinium ylide (4, 272mg, 0.153 mmol), 0.1 equivalents of trimethylamine (16 mg,0.015 mmol) in15 mL EtOH were refluxed in a pre-heated oilbath (80 C) under the blanket of nitrogen for 30 min till the completion of reaction (TLC, 20 % dicholromethane in hexanes; Rf = 0.3). The reaction mixture was diluted with dichloromethane (10 mL) and the organic solution was washed with water (20 mL) and brine (20 mL) and dried over anhydrousNa2SO4. Column chromatographic purification on silica gelwith increasing amount of dichlormethane in hexanes provided 8a as a free flowing solid in about 88 % yield. Analytical samples were obtained through from the recrystallization in EtOH.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 17282-40-5, 1-(2-Ethoxy-2-oxoethyl)pyridin-1-ium bromide.

Reference:
Article; Tangeti, Venkata Swamy; Vasundhara; Satyanarayana; Pavan Kumar, Kaja Srinivas; Asian Journal of Chemistry; vol. 29; 7; (2017); p. 1525 – 1532;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem