Month: April 2022

Reference of 4434-13-3 ,Some common heterocyclic compound, 4434-13-3, molecular formula is C7H7NO2, 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 stirred solution of 5-methylpicolinic acid (2.5 g, 18 mmol) in 50C12 (10 mL) was slowly added DMF (21.3 mg, 3 mmol). The resulting solution was heated to 72 oC for 12h. After cooling to room temperature, the mixture was diluted with toluene and concentrated to near dryness in vacuo. MeOH was added to the obtained oily residue. The contents were stirred for 2 h at 30 oC. After filtration, aq.15% Na2CO3 was added to the filter cake to adjust its pH to 7, and then washed with cold MeOH to afford the title compound (220 mg). MS (ES) m/z 186 (M+H).

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. 4434-13-3, 5-Methylpicolinic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CORVUS PHARMACEUTICALS, INC.; HUDSON, Ryan; BEAUSOLEIL, Anne-Marie; (616 pag.)WO2018/89261; (2018); A2;,
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.73406-50-5, name is Ethyl 3-hydroxypicolinate, molecular formula is C8H9NO3, molecular weight is 167.162, as common compound, the synthetic route is as follows.Formula: C8H9NO3

3-Hydroxy-picolinic acid (15.6 g, 42.1 mmol), ethanol (360 mL), benzene (100 mL) and 98% sulfuric acid (6 mL) were heated under reflux for 40 h. After evaporation of the ethanol and benzene, the residue was dissolved in water, neutralized with sodium bicarbonate, and extracted with chloroform. The organic layer was dried (MgS04), filtered, and then the solvent was evaporated to give ethyl 3-hydroxy-picolinate as a brown oily residue (11.0 g).A mixture of ethyl 3-hydroxy-picolinate (11.0 g, 65.8 mmol), ethyl bromoacetate (12.1 g, 72.4 mmol) and anhydrous potassium carbonate (11.8 g, 85.5 mmol) in acetone (120 mL) was heated under reflux for 15 h. After cooling, the inorganic material separated by filtration. The filtrate was dissolved in chloroform, washed with water, then brine and dried (MgSO4), filtered, and the solvent was evaporated to give a brown oily residue. The residue was purified by flash chromatography using a gradient of ammoniated methanol in chloroform to give ethyl 2- (2-ethoxycarbonyl-3-pyridyloxy) acetate (13.7 g) as a yellow oil (13.7 g). Ethyl 2- (2-ethoxycarbonyl-3-pyridyloxy) acetate (13.6 g, 54.0 mmol) and sodium ethoxide (8. 08 g, 118.8 mmol) in toluene (200 mL) were heated under reflux for 18 h. After cooling, a precipitate was collected by filtration, dissolved in the minimum amount of hot water (about 300 mL), and acidified with acetic acid (6 mL). The resulting precipitate was filtered, and dried in vacuo to give ethyl 3-hydroxyfuro [3,2-b] pyridine-2-carboxylate as a solid (7.0 g). Ethyl 3-hydroxyfuro [3,2-b] pyridine-2-carboxylate (6.90 g, 25.8 mmol) was dissolved in 10% hydrochloric acid (50 mL), and heated under reflux for 3 h. Evaporation of the hydrochloric acid solution gave furo [3,2-b] pyridin-3 (2H)-one hydrochloride (9.0 g). A portion of the furo [3,2-b] pyridin-3 (2H) -one hydrochloride was converted to its free base by treatment with saturated sodium bicarbonate and extraction with chloroform in preparation for the following step. N, N-Diisopropylethylamine (1.08 g, 8.34 mmol) was added slowly to a solution of furo [3,2-b] pyridin-3 (2H) -one (1.40 g, 7.25 mmol) in dry dichloromethane (60 mL) under nitrogen at-10°r; C. Then trifluromethanesulfonic anhydride (2.45 g, 8.70 mmol) was added slowly. The mixture was warmed to RT, and stirred overnight. The reaction was quenched with water. The organic layer was washed with water and brine, dried (MgS04), and then the solvent was evaporated to give a brown oily residue, which was purified by flash chromatography using chloroform to give the sub-title compound (980 mg) as a light-brown oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,73406-50-5, Ethyl 3-hydroxypicolinate, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2005/42538; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 103577-66-8, (3-Methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl)methanol, 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, COA of Formula: C9H10F3NO2, blongs to pyridine-derivatives compound. COA of Formula: C9H10F3NO2

Ph3PO (43.78 g, 157.5 mmol) was dissolved in toluene (100 mL) in a 500 mL three-necked flask and BTC(14.84 g, 50 mmol) was dissolved in toluene (60 mL) and placed in a 150 mL constant pressure dropping funnel,BTC was added dropwise at room temperature, and the temperature was raised to 60 ° C after completion of the dropwise addition.After incubation for 4 hours, 2-hydroxymethyl-3-methyl-4- (2,2,2-trifluoroethoxy) pyridine(33.15 g, 150 mmol) was dissolved in 75 mL of toluene and added at 40 ° C to precipitate a white solid. After the reaction was carried out for 2 hours, the reaction was stopped and the white solid was obtained by filtration to dryness 2-chloromethyl-3-methyl-4- (2,2,2-trifluoroethoxy) pyridine hydrochloride 40.01 g, product yield 97percent

The synthetic route of 103577-66-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhejiang University of Technology; Hainan Weikang Pharmaceutical (Qianshan) Co., Ltd.; Weng Yiyi; Su Weike; Wang Jincan; Wang Ningqing; Zhong Da; Zhu Zhixin; (27 pag.)CN107011252; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 49669-13-8, name is 2-Acetyl-6-bromopyridine. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 2-Acetyl-6-bromopyridine

A solution of l-(6-bromopyridin-2-yl)ethanone (2.9636 g, 14.82 mmol) in methanol (40 mL) at 0C was charged with sodium borohydride (1.682 g, 44.4 mmol) and then allowed to warm to room temperature. After 2.5 hours, the reaction mixture was diluted with dichloromethane (60 mL) and water (60 mL) and the layers were separated. The organic layer was dried over sodium sulfate, filtered, and concentrated to yield the title compound. Calc’d for C7H9BrNO [M+H]+: 204, Found: 204.

With the rapid development of chemical substances, we look forward to future research findings about 49669-13-8.

Reference:
Patent; MERCK & CO., INC.; WO2008/156726; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 23056-47-5, Adding some certain compound to certain chemical reactions, such as: 23056-47-5, name is 2-Bromo-4-methyl-5-nitropyridine,molecular formula is C6H5BrN2O2, 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 23056-47-5.

Into a 2L 3 -necked round-bottom flask under N2 atmosphere, was placed 2-bromo-4- methyl-5-nitropyridine (100 g, 460.79 mmol, 1 equiv), methyl 2,2-difluoro-2- (fluorosulfonyl)acetate (177.0 g, 921.57 mmol, 2 equiv), and Cul (70.2 g, 368.60 mmol, 0.800 equiv) in DMF (1 L). The resulting solution was stirred for 14 h at 120 C and then diluted with NH4CI (3 L), NH4OH (0.5 L). The resulting solution was extracted with ethyl acetate and the combined organic layer was concentrated under reduced pressure. The residue was applied onto a silica gel column and eluted with petroleum ether to give (40 g, 41.94%) of the title compound as a red oil. GC-MS: (ES, m/z): [M]+ 206.

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. 23056-47-5, 2-Bromo-4-methyl-5-nitropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; IDEAYA BIOSCIENCES, INC.; ALAM, Muzaffar; ASWAD, Fred; BECK, Hilary Plake; DILLON, Michael Patrick; GONZALEZ-LOPEZ, Marcos; HATA, Yujiro; SUTTON, JR., James Clifford; (0 pag.)WO2019/236766; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1049744-89-9, 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. 1049744-89-9, name is 2-Hydrazino-5-(trifluoromethyl)pyridine, HCl. A new synthetic method of this compound is introduced below.

(2) Subsequently, Journal of Chemical Society Perkin Trans I (J. Chem. Soc. Perkin trans. I), p. 1875 (in 1988), it gave way to Ethoxy methylene ethyl acetoacetate (6.1g) and the above-described 5- (2-trifluoromethyl synthesized as described in the methyl) pyridin-2-yl hydrazine hydrochloride (7.0g ) water (40), ethanol (40) was added to a solvent mixture, and addition of sodium hydroxide (2.6g), the reaction mixture was stirred for 3 hours at reflux temperature and further stirred for one hour. The reaction solution was treated with a 1N aqueous hydrochloric acid solution, and by purifying the precipitated solid with ethyl acetate-hexane mixed solvent -n- 5-methyl-1- [5- (trifluoromethyl) pyridin-2-yl] -1H- pyrazol to give the 4-carboxylic acid (6.5g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1049744-89-9, its application will become more common.

Reference:
Patent; Mitsubishi Tanabe Pharma Corporation; Watanabe, Masayuki; Furukawa, Hiroyuki; Hamada, Maiko; Fuji, Naoto; Ushio, Hiroyuki; Takashima, Toru; (81 pag.)KR2015/2661; (2015); A;,
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.867279-13-8, name is 4-Bromo-2-chloro-5-methylpyridine, molecular formula is C6H5BrClN, molecular weight is 206.4676, as common compound, the synthetic route is as follows.HPLC of Formula: C6H5BrClN

General procedure: General Procedure A: (0312) A mixture of an arylbromide or aryliodide (1 mmol), an arylboronic acid, aryldioxaborolane or bis(pinacolato)diboron (1.5 mmol), a palladium catalyst (0.1 mmol) and K2CO3 (2-3 mmol) was placed in a reaction vessel which was then thoroughly purged with argon. Dioxane (3 mL) and water (1.5 mL) were added, and the mixture was stirred at 80-95 C. for 1 to 4 h. After cooling to rt, the mixture was poured into EtOAc/H2O (1:1, 10 mL) and the aqueous layer was extracted with EtOAc (5 mL×2). The combined organic extracts were dried (Na2SO4), filtered and concentrated under reduced pressure. Purification of the resultant residue by silica gel chromatography (EtOAc/heptanes) afforded the desired biaryl product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,867279-13-8, 4-Bromo-2-chloro-5-methylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; Janssen Pharmaceutica NV; Meegalla, Sanath; Player, Mark R.; Huang, Hui; Winters, Michael P.; (98 pag.)US2017/291908; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 84199-61-1 ,Some common heterocyclic compound, 84199-61-1, molecular formula is C7H6BrNO, 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 (= reaction 1): 100 mg 3-Acetyl-2-bromopyridine, 140 mg 5-ethynyl- 1 ,2,3- trimethoxybenzene 2Lambda, 101 triethylamine, 17 mg triphenylphosphinpalladium(II) chlorid, 1 mg Cu(I)I were suspended in 4 mL THF under argon atmosphere and stirred for 1 h at 25C. The mixture was diluted with DCM and extracted with diluted aq. N¾ and saturated NH4CI solution. The orgranic phase was concentrated and the the mixture separated via FCC (10 g S1O2, Cyclohexane -> cyclohexane /ethylacetate 70:30) to yield 90 mg l-(2-(3,4,5- trimethoxyphenylethynyl)pyridin-3-yl)ethanone as solid. Analysis: HPLC-MS: Rt = 1.21 min (method E) M+H = 312.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,84199-61-1, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HOFFMANN, Matthias; BISCHOFF, Daniel; DAHMANN, Georg; KLICIC, Jasna; SCHAENZLE, Gerhard; WOLLIN, Stefan Ludwig Michael; CONVERS-REIGNIER, Serge Gaston; EAST, Stephen Peter; MARLIN, Frederic Jacques; MCCARTHY, Clive; SCOTT, John; WO2013/14060; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 1221171-70-5, name is 2-Chloro-6-(trifluoromethoxy)pyridine. A new synthetic method of this compound is introduced below., Recommanded Product: 1221171-70-5

Butyllithium (1.56 M in hexanes, 5.7 mL, 8.9 mmol, 1.1 equiv.) was added dropwise at 0 C to a solution of diisopropylamine (1.2 mL,8.9 mmol, 1.1 equiv.) in THF (15 mL). A solution of 2-chloro-6-(trifluoromethoxy)pyridine 2 (1.6 g, 8.1 mmol, 1 equiv.) in THF (5 mL) was added dropwise at-78 C, and the reaction mixture was stirred for 2 h at this temperature. Chlorotrimethylsilane (1.0 g, 1.13 mL,8.9 mmol, 1.1 equiv.) was then added dropwise and the mixture was allowed to reach 25 C before being neutralised with water (20 mL) andextracted with diethyl ether (3 ×10 mL). The combined organic layerswere dried over sodium sulphate and concentrated in vacuo. The crude product was distilled under reduced pressure to afford pure 2-chloro-6-(trifluoromethoxy)-5-(trimethylsilyl)pyridine (3). Colourless oil (1.5 g,68%), b.p.= 89-93 C (14 mbar); 1H NMR (CDCl3, 300 MHz, 25 C): delta7.78 (d, 1H, J =7.6 Hz, H-3), 7.22 (d, 1H, J =7.6 Hz, H-4), 0.34 (s,9H, SiMe3) ppm.

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, 1221171-70-5, 2-Chloro-6-(trifluoromethoxy)pyridine.

Reference:
Article; Landelle, Gregory; Schmitt, Etienne; Panossian, Armen; Vors, Jean-Pierre; Pazenok, Sergiy; Jeschke, Peter; Gutbrod, Oliver; Leroux, Frederic R.; Journal of Fluorine Chemistry; vol. 203; (2017); p. 155 – 165;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 184368-74-9 ,Some common heterocyclic compound, 184368-74-9, molecular formula is C12H19NO4, 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 1 -(tert-butyl)4-methyl-3 ,6-dihydropyridine- 1 ,4(2H)-dicarboxy-late (1.7 g, 7.3 mmol) in DCM (20 ml) at -78 C was added DIBAL-H (1.0 M in toluene,10.5 ml, 10.5 mmol) followed by stirring at RT for 16 h. The reaction was cooled to 0C and quenched with water and extracted with DCM. The organic layer was dried,filtered and concentrated under reduced pressure to give 1.5 g of the title compound asgreenish viscous liquid. LC-MS: mlz 214 (M+H) +.

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. 184368-74-9, 1-tert-Butyl 4-methyl 5,6-dihydropyridine-1,4(2H)-dicarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ORION CORPORATION; DIN BELLE, David; MAeKELAe, Mikko; PASSINIEMI, Mikko; PIETIKAeINEN, Pekka; RUMMAKKO, Petteri; TIAINEN, Eija; VAISMAA, Matti; WOHLFAHRT, Gerd; (254 pag.)WO2018/115591; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem