Category: pyridine-derivatives

Electric Literature of 167884-17-5, 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. 167884-17-5, name is Imidazo[1,2-a]pyridin-5-ylmethanol. A new synthetic method of this compound is introduced below.

To a solution of imidazo[l,2-a]pyridin-5-ylmethanol (0.150 g, 1.01 mmol, 1 eq) in DMF (2 mL) was added ethyl 3-bromopropanoate (367 mg, 2.02 mmol, 2 eq), NaOH (121 mg, 3.04 mmol, 3 eq) and TBAI (3.74 mg, 0.010 mmol, 0.01 eq). The mixture was stirred for 16 h at 50C. The reaction was quenched with water (10 mL), the aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with brine, dried over MgS04 and concentrated in vacuo. The residue was purified by prep-TLC (Si02, DCM/MeOH = 10/1, Rf = 0.42) to give ethyl 3-(imidazo[l,2-a]pyridin-5-ylmethoxy)propanoate (0.04 g, 13% yield, 80% purity) as a yellow oil, LCMS: m/z = 249.3 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,167884-17-5, Imidazo[1,2-a]pyridin-5-ylmethanol, and friends who are interested can also refer to it.

Reference:
Patent; PIPELINE THERAPEUTICS, INC.; XIONG, Yifeng; SCHRADER, Thomas; CHEN, Austin; ROPPE, Jeffrey Roger; BACCEI, Jill Melissa; BRAVO, Yalda; (199 pag.)WO2019/241131; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 936841-69-9, 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 936841-69-9 as follows.

To a solution of 4-(trifluoromethyl)pyridine-2-carbonitrile (1.7 g, 9.88 mmol) in methanol (18 ml) was added sodium methoxide (25 wt% in MeOH) (2.1 g, 9.9 mmol, 2.3 ml) and the mixture stirred at room temperature for 3 hours. The reaction mixture was concentrated to dryness, the residue suspended in methylamine (33 wt% in EtOH) (25 ml, 200.9 mmol) to which was added methylamine hydrochloride (6.7 g, 99.2 mmol). The reaction mixture was heated in a closed high pressure vial at 90C overnight. After cooling, the mixture was concentrated and the residue treated with dichloromethane, filtered and the filtrate evaporated under reduced pressure. This material was dissolved in diethyl ether, treated with a 2M hydrochloric acid solution in diethyl ether under cooling, stirred at 5-10C for 20 minutes, then diluted with water. The layers were separated and the organic phase washed twice with water. The combined aqueous phases were basified to pH 12 by addition of an aqueous 30% sodium hydroxide solution under cooling, and the product thoroughly extracted with diethyl ether (4x). The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure to afford N,N’-dimethyl-4-(trifluoromethyl)pyridine-2-carboxamidine as an oil (0.70 g), which was used without further purification. LCMS (method 1 ): 218 (M+H)+, retention time 0.28 min. 9F-NMR (MeOD, ppm) -66.4.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,936841-69-9, its application will become more common.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; MUEHLEBACH, Michel; JUNG, Pierre, Joseph, Marcel; EDMUNDS, Andrew; EMERY, Daniel; BUCHHOLZ, Anke; (145 pag.)WO2017/16910; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1221171-96-5, 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 1221171-96-5 as follows.

A 0.36 M solution of intermediate 6a in THF (42 mL, 15.12 mmol) was added to a stirred mixture of 4-bromo-2-methoxy-6-methylpyridine (CAS: 1083169-00-9; 2.98 g, 14.75 mmol) and Pd(/-Bu3P)2 (0.22 g, 0.31 mmol) at rt under N2. The mixture was stirred at reflux for 16 h. After cooling to rt a (1 : 1) mixture of a 32% solution of NFl·, (0369) (50 mL) and a saturated solution of NELCl (50 mL) was added. The mixture was extracted with EtOAc (200 mL). The organic layer was separated, dried (MgS04), filtered and the solvents were evaporated in vacuo. The crude product was purified by flash column chromatography (silica, EtOAc in heptane, gradient from 0/100 to 50/50). The desired fractions were collected and concentrated in vacuo to yield intermediate 7b as a colorless oil (4.34 g, 91%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1221171-96-5, its application will become more common.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BARTOLOME-NEBREDA, Jose Manuel; TRABANCO-SUAREZ, Andres, Avelino; DE LUCAS OLIVARES, Ana Isabel; TRESADERN, Gary John; CONDE-CEIDE, Susana; (212 pag.)WO2019/243528; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1190320-33-2, 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. 1190320-33-2, name is 6-Fluoro-1H-pyrrolo[3,2-b]pyridine, molecular formula is C7H5FN2, 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.

step 4: To a solution of 6-fluoro-lH-pyrrolo[3,2-b]pyridine (9.52 g, 70 mmol) in THF (150 mL) at 0 C was added NaH (60%> in mineral oil, 2.02 g, 84 mmol) in three portions. After stirring at RT for 30 min, the mixture was cooled to 0 C and p-TsCl (14.7 g, 77 mmol) was added. The reaction mixture was stirred for 3 h and the temperature was slowly raised to RT. The reaction mixture was poured into ice- cold water and a precipitate was formed. The precipitate was collected by filtration. The crude product was purified by S1O2 chromatography eluting with DCM to afford 18 g (80%) of 6-fluoro-l -tosyl-lH- pyrrolo[3,2-b]pyridine as a solid. MS (ESI): m/z = 291.1 [M+l]+.

According to the analysis of related databases, 1190320-33-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; ALIAGAS-MARTIN, Ignacio; CRAWFORD, James John; MATHIEU, Simon; RUDOLPH, Joachim; LEE, Wendy; WO2013/92940; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 42182-25-2, 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 42182-25-2, name is 1-(2-Aminopyridin-4-yl)ethanone. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of crude l-(2-aminopyridin-4-yl)ethanone (estimate 1.0 mmol) in MeOH (5 mL) was added NaBH4 (75.7 mg, 2.0 mmol). The mixture was stirred at room temperature overnight, quenched with cold H2O, and extracted with EtOAc. The combined organic layer was evaporated under reduced pressure to provide crude l-(2-aminopyridin-4-yl)ethanol.

According to the analysis of related databases, 42182-25-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IRM LLC; CHE, Jianwei; CHEN, Bei; DING, Qiang; HAO, Xueshi; HE, Xiaohui; JIANG, Songchun; JIN, Qihui; JIN, Yunho; LIU, Hong; LIU, Yahua; OKRAM, Barun; UNO, Tetsuo; WU, Xu; YANG, Kunyong; ZHU, Xuefeng; WO2011/14515; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 605661-83-4, 2-Amino-4-chloronicotinic acid, 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, HPLC of Formula: C6H5ClN2O2, blongs to pyridine-derivatives compound. HPLC of Formula: C6H5ClN2O2

A solution of 2-amino-4-chloronicotinic acid (1.0 g, 5.84 mmol), a catalytic amount of DMF and S0C12 (2.13 mL, 29.2 mmol) in 1 ,2-dichloroethane (12 mL) was heated at 80 C for 4 hours. The reaction mixture was concentrated under vacuum. A solution of the crude compound in diethyl ether and ammonia was stirred at room temperature for 15 h. The reaction mixture was concentrated under vacuum. The residue was dissolved in triethyl orthoformate and the resulting mixture was heated at 80 C for 16 h. The reaction mixture was again concentrated under vacuum and the crude was purified by column chromatography (silica gel, eluent dichloromethane/methanol 98:2) to afford 5- chloropyrido[2,3-d]pyrimidin-4(3H)-one (100 mg) as a yellow solid. MS (ESI) m/z: 182.31 [C7H4C1N30+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,605661-83-4, 2-Amino-4-chloronicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH; NACRO, Kassoum; (223 pag.)WO2018/21977; (2018); A1;,
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. 88912-24-7, name is 5,6-Dichloropicolinic acid. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 88912-24-7

1. Preparation 5,6-Dichloropyridine-2-carboxylic acid-N-oxide 50% Hydrogen peroxide (38 g, 0.35 mol) was carefully added to a mechanically stirred mixture of trifluoroacetic acid (350 mL) and 5,6-dichloropyridine-2-carboxylic acid (56.4 g, 0.29 mol) at 79 C. After one hour, the reaction mixture was poured into 1 L of saturated aqueous NaHSO3, stirring vigorously and cooling in an ice bath. The precipitate was collected and dried to provide 5,6-dichloropyridine-2-carboxylic acid-N-oxide (62.9 g, 0.30 mol), mp 160 C.

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, 88912-24-7, 5,6-Dichloropicolinic acid.

Reference:
Patent; Balko, Terry William; Buysse, Ann Marie; Epp, Jeffrey Brian; Fields, Stephen Craig; Lowe, Christian Thomas; Keese, Renee Joan; Richburg III, John Sanders; Ruiz, James Melvin; Weimer, Monte Ray; Green, Renard Antonio; Gast, Roger Eugene; Bryan, Kristy; US2003/114311; (2003); 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. 59105-50-9, name is (5-Bromopyridin-3-yl)(phenyl)methanone. A new synthetic method of this compound is introduced below., Computed Properties of C12H8BrNO

(1S,4S)-5-(5-Benzoyl-3-pyridyl)-2-(tert-butoxycarbonyl)-2,5-diazabicyclo[2.2.1]heptane In a sealed pressure tube under a nitrogen atmosphere, 3-benzoyl-5-bromopyridine (0.542 g, 2.1 mmol), (1S,4S)-N-(tert-butoxycarb- onyl)-2,5-diazabicyclo[2.2.1]heptane (0.475 g, 2.4 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.04 g, 0.04 mmol), rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.05 g, 0.08 mmol), sodium tert-butoxide (0.380 g, 3.8 mmol) and anhydrous toluene (20 mL) were stirred at 90 C. for 20 h. The reaction mixture was cooled to room temperature and diluted with water (200 mL) and then extracted with diethyl ether (100 mL). The diethyl ether extract was dried (MgSO4), filtered and concentrated by rotary evaporation. The residue was purified by flash chromatography on silica gel, using a gradient of 50% to 80% ethyl acetate:hexane as eluent, to yield 0.364 g (48%) of a yellow oil.

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, 59105-50-9, (5-Bromopyridin-3-yl)(phenyl)methanone.

Reference:
Patent; Targacept, Inc.; US6852721; (2005); B2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 90145-48-5 ,Some common heterocyclic compound, 90145-48-5, molecular formula is C6H5BrN2O, 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.

Example 2 tert-Butyl 2-(6-carbamoylpyridin-3-yl)-5-fluoro-lH-indole-l-carboxylatel-(t°t-Butoxycarbonyl)5-fiuoroindole-2-boronic acid (1 mmol), 5-bromopyridine-2- carboxamide (lmmol), Pd(dppf)Cl2 (0.05 mmol) and 2M Na2CO3 (aq.) (1.5 mL) solution were mixed in THF/water 5:1 (10 mL) in a 20 mL microwave vial. The reaction mixture was stirred at 1200C in the microwave reactor for 15 min. Water was added and the solution was extracted with EtOAc. The organic extracts were dried over Na2SO4, filtered and concentrated to afford a crude mixture which was purified by flash chromatography (Heptane/EtOAc gradient) to give the title compound (200 mg). 1H NMR delta ppm 8.75 (s, 1 H) 8.12 – 8.23 (m, 2 H) 8.07 – 8.13 (m, 2 H) 7.68 (br. s., 1 H) 7.48 (dd, 1 H) 7.15 – 7.32 (m, 1 H) 6.92 (s, 1 H) 1.30 (s, 9 H); MS m/z (M+H) 356.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,90145-48-5, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; WO2008/108729; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 38186-84-4 ,Some common heterocyclic compound, 38186-84-4, molecular formula is C6H5ClFN, 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-Fluoro-3-methyl-2-pyridinamine (DIl): To a solution of 2-chloro-5-fluoro-3-methylpyridine DlO (0.50 g) in dry toluene (12.5 ml) were added sodium t-butoxyde (0.462 g, 4.81 mmol), Pd2(dba)3 (0.315 g, 0.344 mmol), BINAP (0.642 g, 1.031 mmol) and benzophenone imine (0.692 ml, 4.12 mmol). The resulting mixture was degassed (3 x pump/N2) and then heated to 80 0C. After 1 hour stirring, the mixture was cooled down to room temperature, diluted with Et2O (400 ml) and filtered through a celite pad. Volatiles were evaporated, the resulting oil was dissolved in THF (34 ml) and HCl (1.408 ml of a 2 M aqueous solution, 2.82 mmol) was added. The mixture was stirred at room temperature for 1.5 hours, then neutralized with a saturated NaHCO3 aqueous solution and diluted with DCM (200 ml). The inorganic layer was back- extracted with DCM (2 x 50 ml). The collected organic layers were dried (Na2SO4), filtered and evaporated. The residue was purified by flash chromatography on silica gel (Biotage SP4 12M column, Cy/EtOAc 60/40). Collected fractions gave the title compound DIl (0.20 g) as an orange solid. MS: (ES/+) m/z: 127 (M+l). C6H7FN2 requires 126. 1H NMR (400 MHz, DMSO-J6) delta ppm: 7.73 (d, 1 H), 7.23 (dd, 1 H), 5.60 (bs, 2 H), 2.04 (s, 3 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. 38186-84-4, 2-Chloro-5-fluoro-3-picoline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXO GROUP LIMITED; ALVARO, Giuseppe; AMANTINI, David; WO2010/72722; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem