Pyridine-derivatives

Electric Literature of 60154-05-4, 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.60154-05-4, name is 5-Iodo-1-methylpyridin-2(1H)-one, molecular formula is C6H6INO, molecular weight is 235.0224, as common compound, the synthetic route is as follows.

5 -((tert-butyldimethylsilyl)oxy)-6-chloro- 1H-indazole (0.70 g) and 5 -iodo- 1-methylpyridin-2(1H)-one (Example 1, Step B) (0.64 g, 2.7 mmol) were mixed in toluene(2 mL) and heated gently to dissolve at 50C. The resulting mixture was evacuated andpurged with N2 several times. Potassium phosphate (0.43 mL, 5.2 mmol) and (1S,2S)-cyclohexane-1,2-diamine (0.060 mL, 0.50 mmol) were added, followed by copper(I) iodide (0.028 g, 0.15 mmol). The mixture was then heated to 110C for 19 hr. Afterward, the mixture was cooled to room temperature and diluted with ethyl acetate (120 mL), washed with 1M HC1 (50 mL), and saturated ascorbic acid (30 mL). The organic andaqueous layers were separated on a phase separator. The organic layer was concentrated to yield 1.2 g of the title product as a purple/brown oil that was used in the next step without further purification.

Statistics shows that 60154-05-4 is playing an increasingly important role. we look forward to future research findings about 5-Iodo-1-methylpyridin-2(1H)-one.

Reference:
Patent; ASTRAZENECA; RIPA, Lena, Elisabeth; LAWITZ, Karolina; LEPISTOe, Matti, Juhani; HEMMERLING, Martin; EDMAN, Karl; LLINAS, Antonio; (96 pag.)WO2016/46260; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 20970-75-6, 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. 20970-75-6, name is 2-Cyano-3-methylpyridine, molecular formula is C7H6N2, 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.

EXAMPLE 1; 3-Cycloheptyl-8-((2,6-dichlorophenoxy)methyl)H-imidazo[1,5-a]pyridine; Compound 1A: 3-(Bromomethyl)picolinonitrile To a solution of 3-methylpicolinonitrile (660 mg, 5.6 mmol) in 20 mL of carbon tetrachloride was added NBS (1 g, 5.6 mmol) and dibenzoyl peroxide (200 mg, 0.83 mmol) at RT. The reaction mixture was heated at 80 C. for 2 hr, and then cooled to RT. The resulting solid was filtered off, and the filtrate was concentrated under reduced pressure to provide a residue. The residue was diluted with ethyl acetate, washed with water, dried over Na2SO4 and concentrated under reduced pressure to provide crude material. The crude material was purified via silica gel chromatography (10% ethyl acetate in hexanes) to provide compound 1A (510 mg, 46%) as a pale yellow oil. HPLC Rt (Method A): 1.72 min. LC/MS (m/z)=197 (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 20970-75-6, 2-Cyano-3-methylpyridine.

Reference:
Patent; Li, James J.; Hamann, Lawrence G.; Wang, Haixia; US2006/281750; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 116026-95-0, 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 116026-95-0, name is tert-Butyl (4-formylpyridin-3-yl)carbamate. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of (6Z)-5H-dipyrido[2,3-b:4′,3′-f]azepine-5,6(llH)-dione 6-oxime (80.0 mg, 0.333 mmol), ammonium acetate (0.513 g, 6.66 mmol) , water (0.12 mL) and acetic acid (0.76 mL) was stirred at 80 0C for 3 h. The solution was diluted with ethyl acetate and water, the organic solution was washed with brine, dried over MgSO4 and concentrated. The crude residue was purified by preparative LCMS to yield the desired product (102 mg, 69%). LCMS for C23H22N7O3(MH-H)+: m/z = 444.2.

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 116026-95-0, tert-Butyl (4-formylpyridin-3-yl)carbamate.

Reference:
Patent; INCYTE CORPORATION; WO2007/38215; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 4635-08-9, 5-Bromopyridine-3,4-diamine, 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: C5H6BrN3, blongs to pyridine-derivatives compound. COA of Formula: C5H6BrN3

step 1 : Following the procedures as described in steps 1 – 3 of referential example 13, tert-butyl 2-acetyl- 5H-pyrrolo[3,2-i ]pyrimidine-5-carboxylate was prepared using 2-chloro-5H-pyrrolo[3,2-i ]pyrimidine in place of 5-chloro-lH-pyrrolo[3,2-6]pyridine: lH NMR (400 MHz, CDC13) delta 9.50 (s, 1H), 8.07 (d, J = 3.6 Hz, 1H), 6.93 (d, J = 3.7 Hz, 1H), 2.86 (s, 3H), 1.72 (s, 9H); MS(ESI) m/z: 262.2 [M+l] +.

The synthetic route of 4635-08-9 has been constantly updated, and we look forward to future research findings.

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

Related Products of 1214328-96-7 ,Some common heterocyclic compound, 1214328-96-7, molecular formula is C7H5BrClNO2, 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.

Urea hydrogen peroxide (65.32 g, 347.2 mmol) was added portionwise to a solution of trifluoroacetic anhydride (145.8 g, 694.4 mmol, 96.5 ml_) in dichloromethane (577 ml_) at 0 0C. S-Bromo-e-chloro-pyridine^-carboxylic acid methyl ester (prepared as described in Example 1) (27.18 g, 108.5 mmol) was added to the mixture portionwise and the reaction mixture was stirred at room temperature for 19 h. The reaction was quenched by the addition of water, the phases separated and the organic layer washed with water and saturated aqueous potassium carbonate. The organic layer was dried over magnesium sulphate, filtered and concentrated under reduced pressure to give 3-bromo-6- chloro-pyridine-2-carboxylic acid Lambda/-oxide as a yellow oil. Characterising data for the compound are as follows: 1H NMR (400 MHz1 CD3OD) delta 7.77-7.75 (m, 2H) and 4.01 (s, 3H) ppm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1214328-96-7, its application will become more common.

Reference:
Patent; SYNGENTA LIMITED; WHITTINGHAM, William Guy; HACHISU, Shuji; HOTSON, Matthew Brian; WO2010/149956; (2010); 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 103577-66-8, name is (3-Methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl)methanol. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C9H10F3NO2

f) 2-Chloromethyl-3-methyl-4-(2,2,2-trifluoroethoxy)pyridine hydrochloride 160 ml of toluene were added to 14.9 g (0.067 mole) of 2-hydroxymethyl-3-methyl-4-(2,2,2-trifluoroethoxy)pyridine in methylene chloride followed by distillation of methylene chloride. The solution was purified with 2.7 g of acivated charcoal, filtered and washed with 36 ml of toluene. To this solution 5.4 ml (0.075 mole) of thionyl chloride in 27 ml of toluene were added dropwise and maintained for 3 hours. The gas was removed under vacuum at room temperature, then the resulting mixture was cooled to a temperature of from 0 to 5°C and stirred for one hour. The product was filtered, washed with 3 ml of toluene and dried in a vacuum dryer at 35-40°C. The yield was 15.65 g (84 percent).

With the rapid development of chemical substances, we look forward to future research findings about 103577-66-8.

Reference:
Patent; Krka Tovarna Zdravil, D.D., Novo Mesto; EP1681056; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 56057-19-3, 6-Chloro-5-nitro-2-picoline, 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, Product Details of 56057-19-3, blongs to pyridine-derivatives compound. Product Details of 56057-19-3

Step 1 2-Chloro-3-nitro-6-picoline-N-oxide 2-Chloro-3-nitro-6-picoline (2 g, 11.6 mmol) was added to an ice cooled mixture of trifluoroacetic acid (6 mL) and 30% peracetic acid in acetic acid (6 mL). The mixture was allowed to warm to room temperature over 30 minutes and was heated in a 60 C. oil bath for 5 hours. The mixture was partitioned between methylene chloride (100 mL) and water (50 mL). The pH was adjusted to 8 with 2.5 N sodium hydroxide and the aqueous layer was extracted with more methylene chloride (2*50 mL). The combined methylene chloride layers were dried with magnesium sulfate, filtered and evaporated to give the title compound as a white solid (1.6g). 1 H NMR (CDCl3, 300 MHz) delta2.62(s, Me), 7.35 (d, ArH), 7.66 (d, ArH).

The synthetic route of 56057-19-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck & Co., Inc.; US5498777; (1996); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 69045-83-6, Adding some certain compound to certain chemical reactions, such as: 69045-83-6, name is 2,3-Dichloro-5-(trichloromethyl)pyridine,molecular formula is C6H2Cl5N, 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 69045-83-6.

EXAMPLE 3 Conversion of 2,3-dichloro-5-(trichloromethyl)pyridine to 2,3-dichloro-5- (trifluoromethyl)pyridine. 2,3-dichloro-5-(trichloromethyl)pyridine (5 g, 18.84 mmole), iron(III) chloride (0.153 g, 0.942 mmole) and hydrogen fluoride (2.423 g, 85 mmole) in pyridine solution (70%) was added to an autoclave and heated to 175 C over night. The autoclave was cooled to 130 C and left for stirring additional 5 hours, followed by cooling to 25 C and opened carefully leaving gas phase through a Caustic Lye scrubber. The crude was dissolved in dichloromethane, washed with 1 M NaOH (aq) and water. The organic phase was removed by distillation and the product was obtained by distillation (3.0 g, 73 % yield).

According to the analysis of related databases, 69045-83-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CHEMINOVA A/S; ANDERSEN, Casper Stoubaek; WO2014/198278; (2014); 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.

4-Amino-2-chloro-6-trifluoromethoxypyridine (45); At -78 0C, butyllithium (1.56 M in hexane, 2.2 mL, 3.4 mmol, 1.1 eq) was added dropwise to a solution of 2-chloro-4-iodo-6-trifluoromethoxypyridine (42, 1.0 g, 3.1 mmol) in THF (8 mL) followed after 10 min by benzenesulfonyl azide (0.6 g, 3.4 mmol, 1.1 eq). The reaction mixture was was allowed to reach 25 0C before being treated with a saturated aqueous solution of ammonium chloride (10 mL) and extracted with diethylehter (3 x 8 mL). The combined organic layers were dried over sodium sulfate and evaporated to afford a crude red oil of 4-azido-2-chloro-6- trifluoromethoxypyridine. It was then dissolved in anhydrous diethylether (25 mL) and added dropwise to a suspension of lithium aluminium hydride (130 mg, 3.4 mmol, 1.1 eq) in diehtylether (25 mL). The reaction mixture was heated under reflux for 5 h before being treated with water (10 mL) and extracted with diethylether (3 x 10 mL). The combined organic layers were dried over sodium sulfate before being evaporated. The crude product was purified by chromatography on silica gel using ethyl acetate/cyclohexane (1:9) as eluent which afforded pure 4-amino-2-chloro-6- trifluoromethoxypyridine (45, 0.3 g, 1.4 mmol, 46%) as a yellow oil.1H NMR (CDCl3, 300 MHz): delta = 6.41 (d, J = 1.6 Hz, 1 H), 6.07 (d, J = 1.6 Hz, 1 H),4.30 (bs, 2 H). – 19F NMR (CDCl3, 282 MHz): delta = -56.8 – 13C NMR (CDCl3, 75 MHz): delta = 157.4, 156.7, 149.7, 119.9 (q, J = 260 Hz), 107.6, 96.0. – C6H4ClF3N2O (212): calcd. (%) C 33.90, H 1.90, N 13.18; found C 33.56, H 2.01, N 12.87.

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; BAYER CROPSCIENCE AG; PAZENOK, Sergii; VORS, Jean-Pierre; LEROUX, Frederic, R.; MANTEAU, Baptiste; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; UNIVERSITE DE STRASBOURG; WO2010/40461; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 623585-74-0, Adding some certain compound to certain chemical reactions, such as: 623585-74-0, name is Methyl 2,5-dichloroisonicotinate,molecular formula is C7H5Cl2NO2, 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 623585-74-0.

To a solution of methyl 2,5-dichloroisonicotinate (2.25 g) in THF (50 mL) was added sodium borohydride (0.828 g), ethanol (20 mL) was added dropwise, and the mixture was stirred at 50C for 4 hr. To the reaction mixture was added 1 M aqueous hydrochloric acid solution. The solvent was evaporated under reduced pressure, and the obtained residue was diluted with water, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (1.90 g). MS (ESI+) : [M+H]+177.8.

According to the analysis of related databases, 623585-74-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Takeda Pharmaceutical Company Limited; OGINO, Masaki; KIMURA, Eiji; SUZUKI, Shinkichi; ASHIZAWA, Tomoko; IMAEDA, Toshihiro; FUJIMORI, Ikuo; ARAI, Ryosuke; (82 pag.)EP3156397; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem