Tag: M.W:200-300

Related Products of 153034-82-3 ,Some common heterocyclic compound, 153034-82-3, molecular formula is C6H3FINO, 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 dry 15mL ChemGlass pressure bottle under N2 was added 4-iodo-2- fluoro-3-formylpyridine (314 mg, 1.25 mmol), (2-chloro-4-fluorophenyl)hydrazine (210 mg, 1.31 mmol), and anhydrous NMP (5 mL). The reaction mixture was purged with argon, heated at 185C for 2h, and then at 140C for 36h. The reaction mixture was worked up according to the procedure described in Intermediate 69A and the crude product was purified by Biotage Silica gel chromatography using a 80g Thompson Single Step silica cartridge with a linear gradient from 100% hexanes to 100% CH2CI2 over 12 column volumes to give 63.5 mg (13.6%) of the title compound as a pale yellow solid, LC/MS (Condition B): ret. T = 3.7 min, (M+H)+ 373.88, 375.88 and 149.3mg (30.3%) of the hydrazone intermediate as a pale yellow solid, LC/MS (Condition B): ret. T = 4.2min, (M+H)+ 393.90, 395.90.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,153034-82-3, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; VELAPARTHI, Upender; FRENNESSON, David B.; SAULNIER, Mark G.; AUSTIN, Joel F.; HUANG, Audris; BALOG, James Aaron; VYAS, Dolatrai M.; WO2012/9510; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 102368-13-8, 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. 102368-13-8, name is 1,1′-Thiocarbonylbis(pyridin-2(1H)-one). A new synthetic method of this compound is introduced below.

Step D: 4-Isothiocyanato-6-(methoxymethyl)pyrimidine To a bright orange solution of 1,1′-thiocarbonyldipyridin-2(1H)-one (0.84 g, 3.59 mmol) was in dichloromethane at ambient temperature was added 6-(methoxymethyl)pyrimidin-4-amine (0.5 g, 3.59 mmol). The orange solution was stirred at ambient temperature for 18 h. The solution was purified by column chromatography (0-40% ethyl acetate/hexanes) to afford 4-isothiocyanato-6-(methoxymethyl)pyrimidine (0.32 g, 1.77 mmol, 49% yield) as a yellow solid. 1H NMR (400 MHz, CDCl3) delta ppm 8.91 (1H, d, J=1.26 Hz), 7.19 (1H, d, J=1.01 Hz), 4.52 (2H, s), 3.49 (3H, s). MS (LC/MS) R.T.=1.39; [M+H]+=182.10.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,102368-13-8, 1,1′-Thiocarbonylbis(pyridin-2(1H)-one), and friends who are interested can also refer to it.

Reference:
Patent; Bristol-Myers Squibb Company; US2009/270405; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 86129-63-7, Adding some certain compound to certain chemical reactions, such as: 86129-63-7, name is Ethyl 2,4-dichloro-6-methyl-3-pyridinecarboxylate,molecular formula is C9H9Cl2NO2, 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 86129-63-7.

To a solution of 2- (IH-PYRAZOL-3-YL)-1, 3-THIAZOLE (7.71 g, 1.05 eq) in anh. DMF (61 mL), at 0C, under N2, was added NaH 60% in mineral oil (2.03 g, 1. 05 eq) and the reaction mixture was stirred for 10 min. at 0C and then for 1 hr at room temperature. Intermediate 1 (11.34 g, 48.0 MMOL) was then added as a solution in anh. DMF (35 mL) at 0C and the resulting solution was heated at 110C for 3 hr. The reaction was then quenched with water, extracted with EtOAc, washed with brine, dried over anh. NA2SO4, filtered and concentrated in vacuo. The crude product was purified by flash chromatography (silica gel, cHex/EtOAc 7: 3) to give 7.02 g of the title compound as a white solid. NMR (‘H, CDCl3) : 8 7.91 (d, 1H), 7.91 (d, 1H), 7.41 (d, 1H), 7.31 (s, 1H), 7.18 (d, 1H), 4.50 (q, 2H), 2.78 (s, 3H), 1.25 (t, 3H). MS (M/Z) : 349 [MH] +.

According to the analysis of related databases, 86129-63-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SB PHARMCO PUERTO RICO INC; NEUROCRINE BIOSCIENCES INC; GLAXO GROUP LIMITED; WO2004/62665; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 199296-40-7, name is tert-Butyl (5-formylpyridin-2-yl)carbamate, molecular formula is C11H14N2O3, The 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. Product Details of 199296-40-7

100 g crude acrylic acid ester isomeric mixture prepared according to Example 3 was dissolved in 1 L HCl (5 N) and heated to reflux until complete conversion was achieved. The mixture was cooled to ambient temperature and the pH was adjusted to 7 with concentrated NaOH. The precipitate was filtered off and crystallized from boiling water to yield 25.2 g of 29 (E)-3-(6-Amino-pyridin-3-yl)-2-(1-cyclohexyl-1H-imidazol-4-yl)-acrylic acid. [0288] 1H-NMR (600.2 MHz, CD4OD):=1.34 (m, 2H), 1.52 (m, 2H), 1.77 (m, 4H), 1.94 (m, 2H), 2.18 (m, 2H), 4.22 (dddd, J=1.52, 1.77, 7.42, 8.44, 1H), 6.51 (d, J=7.86 Hz, 1H), 7.19 (d, J=7.82 Hz, 1H), 7.41 (dd, J=4.22, 8.44 Hz, 1H), 7.82 (dd, J=7.19, 7.86 Hz, 1H), 7.86 (dd, J=7.19, 7.82 Hz, 1H), 8.44 (dd, J=4.22, 7.42 Hz, 1H). [0289] HPLC: tR=3.60 (Z) and 3.95 (E) min (YMC_C18 150¡Á4.6 mm, 3 mum, A: 9H2O+1 ACN/0.1 TEA/pH6.5 AcetAc, B: 1H2O+9 ACN/0.1 TEA/pH6.5 AcetAc, 0.8 mL/min, 20 C.

With the rapid development of chemical substances, we look forward to future research findings about 199296-40-7.

Reference:
Patent; SANOFI; BOEHM, Claudius; KLEIN, Susanne; NAPIERSKI, Bernard; SOMMER, Christian; US2013/245274; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 947248-68-2, 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. 947248-68-2, name is 6-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-amine. A new synthetic method of this compound is introduced below.

c) 2,6-Dibromo-[ 1 ,2,4] triazolo[ 1 ,5-a]pyridineA mixture of 6-bromo-[l,2,4]triazolo[l,5-a]pyridin-2-amine (20.86 g, 97.9 mmol), sodi- um nitrite (67.6 g, 979 mmol) and benzyltriethylammonium bromide (53.3 g, 196 mmol) in bromoform (1.47 kg, 508 ml, 5.81 mol) was stirred for 30 minutes at 25 C. Then dichloroacetic acid (25.3 g, 16.2 ml, 196 mmol) was added and the mixture was stirred for 20 hours at 25 C under exclusion of light. 600 ml of water were added to the mixture and stirred for 30 minutes. The mixture was diluted with water and dichloromethane, filtrated over dicalite and the filtrate extracted 3 times with dichloromethane. The organic layers were combined, washed with water, dried over magnesium sulfate, filtrated and evaporated to dryness under reduced pressure. The crude material was purified by flash chromatography in 2 portions over 2 x 70 g silica columns using dichloromethane/methanol 5 % as eluent, affording 2,6-dibromo-[l,2,4]triazolo[l,5- a]pyridine (7 g, 26%) as light brown solid. Mp.: 201C. MS: m/z=277.7/279.9 (M+H+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,947248-68-2, 6-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; FLOHR, Alexander; GROEBKE ZBINDEN, Katrin; KOERNER, Matthias; WO2013/41472; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1214353-79-3, 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 1214353-79-3 as follows.

NaH (2.26 g, 66 mmol) was added in portions to a solution of 2-methoxyethanol (30 mL). The mixture was stirred for 30 min at room temperature. Then 5-bromo-6-chloro-pyridine-2-carboxylic acid methyl ester (Example 9 c, 3 g, 12 mmol) was added and the reaction mixture was heated to 100 C. overnight. The mixture was poured into water and extracted with ethyl acetate (30 mL). The pH of the aqueous layer was adjusted to 2 by addition of 1 N hydrochloric acid and the resulting mixture was extracted with ethyl acetate (3¡Á50 mL). The combined organic extracts were washed three times with brine, dried (sodium sulfate) and evaporated. The crude title compound (2.48 g, yellow solid) was used for the next reaction step without further purification; MS (EI): m/e 276.0 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1214353-79-3, its application will become more common.

Reference:
Patent; Bissantz, Caterina; Grether, Uwe; Hebeisen, Paul; Kimbara, Atsushi; Liu, Qingping; Nettekoven, Matthias; Prunotto, Marco; Roever, Stephan; Rogers-Evans, Mark; Schulz-Gasch, Tanja; Ullmer, Christoph; Wang, Zhiwei; Yang, Wulun; US2012/316147; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 886365-43-1, name is 5-Bromo-3-methylpicolinic acid, molecular formula is C7H6BrNO2, The 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. COA of Formula: C7H6BrNO2

To a solution of compound 7 (4.9 g, 22.68 mmol) in C2H5OH(20 mL) was added H2SO4 (2.2 g, 22.68 mmol) at room temperature.The mixture was heated at 80 C for 8 h. Solvent was concentrated invacuo and EtOAc (200 mL) was added. After washed with water(100 mL¡Á3), the organic phase was dried over Na2SO4, filtered andconcentrated in vacuo. The residue was purified by flash columnchromatography (silica gel, petroleum ether/EtOAc=20/1) to affordethyl 5-bromo-3-methylpicolinate (8, 4.6 g, 83%) as colorless liquid. 1HNMR (300 MHz, DMSO-d6) delta (ppm): 8.62 (s, 1H), 8.14 (s, 1H), 4.34 (q,J=7.1 Hz, 2H), 2.45 (s, 3H), 1.32 (t, J=7.1 Hz, 3H).

With the rapid development of chemical substances, we look forward to future research findings about 886365-43-1.

Reference:
Article; Yuan, Xinrui; Wu, Hanshu; Bu, Hong; Zheng, Peiyuan; Zhou, Jinpei; Zhang, Huibin; Bioorganic and Medicinal Chemistry; vol. 27; 7; (2019); p. 1211 – 1225;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 17282-03-0, 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. 17282-03-0, name is 3-Bromo-2-chloro-5-methylpyridine. A new synthetic method of this compound is introduced below.

Example 143A 3-bromo-5-(bromomethyl)-2-chloropyridine 3-Bromo-2-chloro-5-methylpyridine (4 g, 19.37 mmol), N-bromosuccinimide (3.79 g, 21.3 mmol) and benzoic peroxyanhydride (0.239 g, 0.969 mmol) were combined in carbon tetrachloride (40 mL), heated under reflux for 24 hours, cooled, and filtered to remove succinimide. The filtrate was concentrated. The resulting residue was purified by chromatography (silica gel, 0-30% ethyl acetate in heptanes) to afford the title compound (1.9 g, 34%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,17282-03-0, its application will become more common.

Reference:
Patent; Wang, Le; Pratt, John; Hasvold, Lisa A.; Liu, Dachun; Dai, Yujia; Fidanze, Steven D.; Holms, James H.; Mantei, Robert A.; McDaniel, Keith F.; Sheppard, George S.; McClellan, William J.; US2014/275026; (2014); A1;,
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 53937-02-3, name is 4-Benzyloxy-2-(1H)-pyridone. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C12H11NO2

A mixture of 4-benzyloxy-2(lH)-pyridone (50 mg, 0.0025 mol), 2-bromo-5-iodotoluene (1.13 g, 0.0038 mol), CuI (0.238 g, 0.0015 mol), N,N-dimethylethylenediamine (0.266 ml, 0.0025 mol), and K3PO4 (1.06 g, 0.005 mol) in dioxane/DMF 9:1 (75 ml) was stirred at 180 0C in a microwave for 15 minutes Then, DCM was added. The solid was filtered off through dicalite and the filtrate was washed with NH4OH 32 %. The organic layer was separated, dried over Na2SO4 and the solvent was evaporated. The residue was purified by column chromatography (eluent: DCM). The desired product was collected and evaporated. The resulting product was precipitated with DIPE yielding 0.737 g of intermediate compound 1-11 (80 %).

With the rapid development of chemical substances, we look forward to future research findings about 53937-02-3.

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; WO2008/68265; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 14482-51-0, 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.14482-51-0, name is 2-Bromo-3,5-dichloropyridine, molecular formula is C5H2BrCl2N, molecular weight is 226.89, as common compound, the synthetic route is as follows.

Raw material selection: 17.5 g of 2-bromo-3,5-dichloropyridine, 34.54 g of cuprous cyanide (CuCN), 12.6 g of 2-methylimidazole,The reaction organic solvent dimethylacetamide (DMSO) 105 ml; purified organic solvent n-heptane 100 ml.In the process of extracting and washing the organic solvent (or ethyl acetate or toluene or cyclohexane or petroleum ether) after the completion of the reaction, the amount of the organic solvent and the amount of water are conventional and not limited; the following specific process is toluene Extraction is an example.Reaction step: 17.5 g of 2-bromo-3,5-dichloropyridine prepared above, 34.54 g of cuprous cyanide (CuCN), 12.6 g of 2-methylimidazole were added to a dry 250 ml reaction flask, and an organic solvent was added. 105 ml of dimethylacetamide was heated to 105-110 C under the protection of nitrogen, and the reaction was completely cooled to room temperature.Add 150 ml of toluene in an organic solvent, stir for about 10 minutes, add 100 ml of water, filter the solid, separate the organic phase from the filtrate, and wash the residue twice with toluene (50 ml/time).The washing liquid continues to extract the aqueous phase, and the liquid phase is separated, and the organic phase is combined, washed once with 100 ml of water, and evaporated to dryness under reduced pressure at 60 C in a water bath.Producing a crude solid of 3,5-dichloro-2-cyanopyridine;The crude solid of 3,5-dichloro-2-cyanopyridine obtained is recrystallized from purified organic solvent n-heptane: 100 ml of n-heptane is added and heated to 90 C to dissolve, and then slowly cooled to about 10 C to precipitate a solid, and the product is obtained by filtration. ,Drying at 40-60 C under vacuum gave 9.1 g of 3,5-dichloro-2-cyanopyridine, the yield was 68.2%, the product purity was 99.2%, and the total reaction yield was 64.4%.

The chemical industry reduces the impact on the environment during synthesis 14482-51-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Hangzhou East China Pharmaceutical Group Zhejiang Huayi Pharmaceutical Co., Ltd.; Weifang Haixin Pharmaceutical Co., Ltd.; Lou Qingming; Wu Lei; Lou Lei; (8 pag.)CN109020882; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem