Category: pyridine-derivatives

Synthetic Route of 4548-45-2 , The common heterocyclic compound, 4548-45-2, name is 2-Chloro-5-nitropyridine, molecular formula is C5H3ClN2O2, 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 tert-butyl piperazine-1-carboxylate (64 g, 346 mmol) in 600 ml. of THF at O0C was added NaH (16.4 g, 409 mmol, 60% in mineral oil) portionwise. The reaction mixture was stirred for 15 min and 2-chloro-5-nitropyridine (50 g, 314 mmol) was added. The reaction mixture was allowed to warm to rt and then heated to 5O0C for 4 h. The reaction was quenched by water (30 ml.) and extracted with DCM (1.5 Lx 3). The combined organic layers were dried over Na2SO4 and the solvent was removed under reduced pressure. The residue was subjected to wash with petroleum ether to give the desired product of Step A (80 g, yield 83%). 1H NMR (CDCI3, 400 MHz) delta 8.95 (d, J = 2.4 Hz, 1 H), 8.24 (d, J = 12 Hz, 1 H), 6.92 (d, J = 6.0 Hz, 1 H), 3.75 (s, 4 H), 3.44 (s, 4H), and 1.41 (s, 9 H).

The synthetic route of 4548-45-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2009/32667; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 139022-25-6, 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. 139022-25-6, name is Imidazo[1,2-a]pyridine-6-carboxylic acid, molecular formula is C8H6N2O2, 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.

A solution of imidazo[1 ,2-a]pyridine-6-carboxylic acid (0.100 g, 0.62 mmol), 5-(3-chlorobenzyl)pyridin-2-amine (0.161 g, 0.74 mmol), 1 -[b/s(dimethylamino)methylene]- 7/-/-1 ,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (0.353 g, 0.93 mmol) and A/-A/,A/-diisopropylethylamine (0.240 g, 1 .86 mmol) in A/,A/-dimethylformamide (3 ml_) was stirred at room temperature for 2 h. The crude sample was dissolved in minimal A/,A/-dimethylformamide and purified via prep-HPLC (Boston C18 21 *250 mm 10 pm column; acetonitrile/0.01 % aqueous trifluoroacetic acid) to give A/-(5-(3-chlorobenzyl)pyridin-2-yl)imidazo[1 ,2-a]pyridine-6-carboxamide (0.048 g, 0.1 12 mmol, 18.0%) as a faint yellow solid. 1 H NMR (500 MHz, Dimethylsulfoxide-c/6) d 1 1 .26 (s, 1 H), 9.57 (s, 1 H), 8.41 (d, J = 1 .8 Hz, 1 H), 8.37 (d, J = 2.5 Hz, 1 H), 8.34 (dd, J = 4.8, 4.8Hz, 1 H), 8.22 (d, J = 2.0 Hz, 1 H), 8.12 (d, J = 8.5 Hz, 1 H), 8.02 (d, J = 9.4 Hz, 1 H), 7.77 (dd, J = 8.5, 2.3 Hz, 1 H), 7.36- 7.33 (m, 2H), 7.29-7.25 (m, 2H), 4.00 (s, 2H); LCMS (ESI) m/z: 363.0 [M+H]+.

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 139022-25-6, Imidazo[1,2-a]pyridine-6-carboxylic acid.

Reference:
Patent; YUMANITY THERAPEUTICS, INC.; LE BOURDONNEC, Bertrand; LUCAS, Matthew; OZBOYA, Kerem; PANDYA, Bhaumik; TARDIFF, Daniel; TIVITMAHAISOON, Parcharee; WRONA, Iwona; (475 pag.)WO2019/183587; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 6332-56-5, Adding some certain compound to certain chemical reactions, such as: 6332-56-5, name is 3-Nitropyridin-2(1H)-one,molecular formula is C5H4N2O3, 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 6332-56-5.

2-Oxo-3-nitro-N-(carbomethoxymethyl)-pyridinone (109). 2-Hydroxy-3-nitropyridine 108 (10 g, 71.38 mmole) is mixed with pulverized potassium carbonate (10.9 g, 78.5 mmole) and 30 mL of DMF. After 10 min, methyl bromoacetate (10.4 mL, 107 mmole) is added. The resulting mixture is stirred at room temperature for 4.5 hr. The reaction is quenched by water and extracted by ethyl acetate. The organic layer is then washed with brine, dried over MgSO4, filtered and evaporated to give an oil which is chromatographed over flash silica with EtOAc to give 109.

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. 6332-56-5, 3-Nitropyridin-2(1H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; The Procter & Gamble Company; US5672598; (1997); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 123148-66-3 ,Some common heterocyclic compound, 123148-66-3, molecular formula is C7H9NO2, 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 2: 3-(2, 6-d ifluoro-3 , 5-dimethoxyphenyl)-1-[(2-methoxypyridin-4-yl)methylJ-8-(morpholin-4-ylmethyl)- 7-(phenylsufonyl)-1, 3,4, 7-tetrahydro-2H-pyrrolo[3 ?,2 ?:5, 6Jpyrido[4, 3-dJpyrimidin-2-one To a solution of 3 -(2,6-difluoro-3 ,5 -dimethoxyphenyl)-8-(morpholin-4-ylmethyl)-7- (phenylsulfonyl)- 1,3 ,4,7-tetrahydro-2H-pyrrolo[3 ?,2? : 5,6]pyrido[4,3 -d]pyrimidin-2-one(10.0 mg, 0.0 167 mmol, from Step 1), (2-methoxypyridin-4-yl)methanol (23.2 mg,0.167 mmol, purchased from Ark Pharma, catalog number: AK-2 8607) in tetrahydrofuran (1.0 mL, 12 mmol) were added triphenylphosphine (26.0 mg, 0.099 1 mmol) and diethyl azodicarboxylate (16 iL, 0.10 mmol). The resulting mixture was stirred at 60 C for 12 h. The reaction was diluted with MeOH (4.0 mL) and purified by RP-HPLC (pH 10) toafford the product. LC-MS calculated for C35H35F2N607S [M+H] mlz: 721.2; found 721.0.

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. 123148-66-3, (2-Methoxypyridin-4-yl)methanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; INCYTE CORPORATION; WU, Liangxing; ZHANG, Colin; HE, Chunhong; SUN, Yaping; LU, Liang; QIAN, Ding-Quan; XU, Meizhong; ZHUO, Jincong; YAO, Wenqing; WO2014/7951; (2014); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 131674-39-0, Adding some certain compound to certain chemical reactions, such as: 131674-39-0, name is 1-(2-Chloropyridin-3-yl)ethanol,molecular formula is C7H8ClNO, 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 131674-39-0.

To a solution of 2-chloropyridine (XXIX) (31.0 kg, 273 mol) in dry THF (275 L) cooled to -78oC under nitrogen was added LDA (113 L, 1220 mol) dropwise while maintaining the temperature at -78oC and stirred for 5 hours. Acetaldehyde (16 L, 463 mol) was then added and the reaction was stirred at -78oC for another 5 hours before warming to 0oC and adding water (310 L) to quench the reaction. The solution was stirred for 50 min and then warmed to room temperature. The solution was extracted 3 x EtOAc (279 L) by adding EtOAc, stirring for 50 min, allowing to stand for 50 min, separating the layers and then repeating twice. The combined EtOAc was concentrated under vacuum to a volume of 300-500 L. To the crude 1-(2-chloropyridin-3- yl)ethanol (XXX) was added DCM (705 L) followed by an aqueous solution of KBr (3.3 Kg, 27.7 mol) dissolved in water (33 L). The solution was cooled to 0oC before adding TEMPO (1.7 Kg, 10.9 mol) and then stirred for 50 min. In a second container, water (980 L) was added followed by KHCO3 (268 Kg, 2677 mol) and 10% aqueous NaClO (233 L, 313 mol). This aqueous mixture was then added dropwise to the TEMPO mixture. This combined mixture was stirred at 0oC for 5 hours. To this mixture was added dropwise Na2S2O3*7H2O (22.5 Kg, 90 mol) in water (107 L) with stirring for 50 min at 0oC. The mixture was allowed to warm to room temperature and the organic phase was separated. The aqueous phase was extracted 2 x DCM (353 L) by adding DCM, stirring for 50 min, allowing to stand for 50 min, separating the layers and then repeating. The combined organic layers were washed with aqueous 25% NaCl (274 L) and concentrated under vacuum to give crude 1-(2-chloropyridin-3-yl)ethanone (XXXI) which was used for the next step without additional purification.

According to the analysis of related databases, 131674-39-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SAMUMED, LLC; KC, Sunil Kumar; MITTAPALLI, Gopi Kumar; CHIRUTA, Chandramouli; HOFILENA, Brian Joseph; (128 pag.)WO2019/241540; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 183208-35-7, Adding some certain compound to certain chemical reactions, such as: 183208-35-7, name is 5-Bromo-1H-pyrrolo[2,3-b]pyridine,molecular formula is C7H5BrN2, 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 183208-35-7.

General procedure: To a cold solution of appropriate pyrrolo-pyridines 8a,c,e (2.5 mmol) in anhydrous toluene (25 mL), t-BuOK (0.38 g, 3.4 mmol) and TDA-1 (1 or 2 drops) were added at 0 C. The reaction mixture was stirred at room temperature for 3 h and then MeI (2.5 mmol, 0.2 mL) was added at 0 C. TLC analysis (ethyl acetate) revealed that methylation was complete after 1 h. The solvent was evaporated under reduced pressure. The residue was treated with water, extracted with DCM (3 × 20 mL), dried (Na2SO4), evaporated and purified by column chromatography using DCM/ethyl acetate (9/1) as eluent to give derivatives 8b,d,f [42].

According to the analysis of related databases, 183208-35-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Carbone, Anna; Parrino, Barbara; Vita, Gloria Di; Attanzio, Alessandro; Span, Virginia; Montalbano, Alessandra; Barraja, Paola; Tesoriere, Luisa; Livrea, Maria Antonia; Diana, Patrizia; Cirrincione, Girolamo; Marine Drugs; vol. 13; 1; (2015); p. 460 – 492;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 170886-13-2, name is 2-(Trifluoromethyl)pyridin-4-ol, the common compound, a new synthetic route is introduced below. COA of Formula: C6H4F3NO

An alternative synthetic procedure is provided: 3,4,5-trifluorobenzaldehyde (1.08 g, 6.74 mmol) was added to a solution of 2-trifluoromethyl)pyridin-4-ol (1 g, 6.13 mmol) and potassium carbonate (1.017 g, 7.36 mmol) in Nu,Nu-dimethylformamide (DMF) (10 mL) under nitrogen with stirring. The reaction mixture was stirred at 100 C for 16 h, cooled to rt, and then diluted with EtOAc (30 mL) and water (30 mL). The organic phase was washed three times with water (30 mL), dried over sodium sulphate, and then concentrated in vacuo to afford the title compound (1.8 g, 97%). LCMS (ESI): m/z 304 [M + H]+; 1.17 min (ret time)

The synthetic route of 170886-13-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; SANG, Yingxia; WAN, Zehong; ZHANG, Qing; WO2014/114694; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 58584-63-7, 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. 58584-63-7, name is (6-Methoxypyridin-3-yl)methanol. A new synthetic method of this compound is introduced below.

To a solution of 2-methoxy-5-hydroxymethylpyridine (0.71 g, 0.005mole) in DCM (5 mL) at 0 C under N2, was added thionyl chloride (0.7 mL, 0.009 mole) drop wise. The reaction mixture was warmed to RT and stirred for 2 hours. The reaction mixture was diluted with DCM (50 mL) and treated with saturated aqueous sodium bicarbonate (10 mL). Organic layer was washed with water (20 mL), brine solution (20 mL), dried over Na2SC>4 and concentrated under vacuum to obtain the title compound. Yield: 0.58 g; lH – NMR (CDC13, 400 MHz) delta ppm: 3.94 (s, 3H), 4.55 (s, 2H), 6.75 – 6.77 (d, J = 8.5 Hz, 1H), 7.61 – 7.64 (dd, J = 2.2, 8.5 Hz, 1H), 8.14 (s, 1H); Mass (m/z): 158.0 – 160.0 (M+H) +.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,58584-63-7, (6-Methoxypyridin-3-yl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; SUVEN LIFE SCIENCES LIMITED; NIROGI, Ramakrishna; SHINDE, Anil Karbhari; MOHAMMED, Abdul Rasheed; BADANGE, Rajesh Kumar; JAYARAJAN, Pradeep; BHYRAPUNENI, Gopinadh; JASTI, Venkateswarlu; (172 pag.)WO2018/42362; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1594-58-7 ,Some common heterocyclic compound, 1594-58-7, molecular formula is C6H7N3O, 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.

5-(Chloromethyl)-3-(pyridine-2-yl)-1 ,2,4-oxadiazole (SO2-065): To a solution of N- hydroxypicolinimidamide (0.2g g, 1 .5 mmol) in DCM (20 ml) and chloroacetyl chloride (0.2 g, 1 .8 mmol) at 0 C, diisopropylethylamine (0.23 g, 1 .8 mmol) was added (dropwise). The mixture was warmed up to r.t. and stirred for 24 h. and organic solvent was evaporated and the residue was refluxed overnight in toluene (20 ml_) to complete the cyclization. The product obtained was purified using Si02 chromatography (EtOAc: hexane gradient elution). The required compound SO2-065 (0.24 g, 81 %) was obtained as a white solid.1 H NM R (400 M Hz, CDCI3) delta 8.81 (ddd, J = 4.8, 1 .6, 1 .0 Hz, 1 H), 8.14 (d, J = 7.9 Hz, 1 H), 7.87 (ddd, J = 7.9 Hz, 4.8 , 1 .8 Hz, 1 H), 7.46 (ddd, J = 7.7, 4.8, 1 .2 Hz, 1 H), 4.79 (s, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1594-58-7, its application will become more common.

Reference:
Patent; H. LEE MOFFITT CANCER CENTER AND RESEARCH INSTITUTE, INC.; LAWRENCE, Harshani R.; SEBTI, Said M.; OZCAN, Sevil; WO2012/129564; (2012); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 5470-66-6, name is 4-Nitro-2-picoline N-oxide. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C6H6N2O3

A solution OF 2-METHYL-4-NITROPYRIDINE-N-OXIDE (3.80 g, 24.6 mmol) in 100 ML of acetic acid was slowly heated with iron powder (6.89 g, 124 mmol) in a large flask (caution: the reaction becomes very exothermic upon turning brown). The resulting slurry was heated for 2 hours at 80 C. Excess acetic acid was removed IN VACUO, THE residue was taken up in 20% aqueous sodium hydroxide solution, and 100 mL of chloroform (CHC13) was added and the mixture filtered through CELITES FILTER aid. The aqueous phase was extracted with two 200 mL portions of chloroform. The combined organic layers were dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude product (2.2 g, 83% yield) was used without further purification. A solution OF KI (1. 96 g, 11. 9 mmol) and 12 (1.87 g, 7.36 mmol) in 10 ML of water was added to a REFLUXING solution of the 2-methylpyridin-4-ylamine (1.00 g, 9.25 mmol) and sodium carbonate (683 mg, 6.44 mmol) in 5 ML of water. The mixture was heated at reflux for 2 hours, cooled to room temperature, and treated with 20 mL of ethyl acetate (EtOAc). Phases were separated and the aqueous layer was extracted with three 20 ML portions of ethyl acetate. The combined organic layers were washed with a saturated aqueous sodium thiosulfate (NA2S203) solution, dried over magnesium sulfate, and concentrated ILL vacuo. Flash chromatography (30% ethyl acetate in hexanes to 100% ethyl acetate, gradient) of the resulting residue yielded 4-amino-3-iodo-6-methylpyridine (first eluting: 226 mg, 11% yield) and 4- AMINO-3-IODO-2-METHYLPYRIDINE (second eluting : 116 mg; 5% yield).

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, 5470-66-6, 4-Nitro-2-picoline N-oxide.

Reference:
Patent; BOEHRINGER INGELHEIM PHARMACEUTICALS, INC.; WO2005/30213; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem