Category: pyridine-derivatives

Application of 17228-69-2 ,Some common heterocyclic compound, 17228-69-2, molecular formula is C6H6ClNO, 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.

Deprotonation of this compound with n-butyllithium and reaction with 2-chloro-4-methoxypyridine in dry benzene yields the title compound of m.p. 166 C. (decomposition).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,17228-69-2, its application will become more common.

Reference:
Patent; Byk Gulden Lomberg Chemische Fabrik Gesellschaft mit beschrankter Haftung; US4472409; (1984); 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.13535-01-8, name is 5-Bromopyridin-3-amine, molecular formula is C5H5BrN2, molecular weight is 173.01, as common compound, the synthetic route is as follows.Computed Properties of C5H5BrN2

[0612] To a solution of 3-amino-5-bromo pyridine (XVIII) (1.0 g, 5.78 mmol) in dry pyridine (10 inL) was added pivaloyl chloride (XIX) (769 mg, 6.38 mmol). The reaction mixture was stirred at room temperature for 3 h. The reaction was poured into an ice water/saturated aqueous NaHCC mixture and stirred for 30 min. The precipitate was filtered, washed with cold water and dried at room temperature to yield N-(5-bromopyridin-3-yl)pivalamide (XX) as an off- white solid (1.082 g, 4.22 mmol, 73.1% yield). NMR (OMSO-d6, 500 MHz) delta ppm 1.23 (s, 9H), 8.37 (d, J=2Hz, IH), 8.39 (t, J=2Hz, IH), 8.80 (d, J=2Hz, IH), 9.58 (brs, IH); ESIMS found CioHi3BrN20 mlz 258.9 (Br81M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,13535-01-8, 5-Bromopyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; SAMUMED, LLC.; KC, Sunil Kumar; WALLACE, David Mark; CAO, Jianguo; CHIRUTA, Chandramouli; MARAKOVITS, Joseph Timothy; BOLLU, Venkataiah; HOOD, John; (293 pag.)WO2017/23988; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 7598-35-8, Adding some certain compound to certain chemical reactions, such as: 7598-35-8, name is 2-Bromopyridin-4-amine,molecular formula is C5H5BrN2, 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 7598-35-8.

2.8 g (32.2 mmol, 2 eq) of pyruvic acid (initial product 1 ) were poured into a 50 mL single collar flask, 20 mL of thionyl was added to this and it was heated at reflux for 2 hours. After 2 hours, the reaction mixture was dry concentrated by azeotroping several times with dry toluene. 2.8 g (16.1 mmol, 1 eq) of 2-bromo-pyridin-4-ylamine (initial product 2), diluted in 5 mL of pyridine, was then added, drop-by-drop at 0C, and the mixture agitated at ambient temperature for 16 hours. The reaction mixture was diluted with 50 mL of ethyl acetate, washed with 50 mL of an aqueous solution of saturated sodiumbicarbonate, followed by 3 x 50 mL of water. The organic phase was dry concentrated. The residue was chromatographed on silica with a heptanes / ethyl acetate mixture (2/1 v/v) as eluent. N-(2-bromo-pyridin-4-yl)-2-oxo-propionamide was obtained in the form of a white solid.

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. 7598-35-8, 2-Bromopyridin-4-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GALDERMA RESEARCH & DEVELOPMENT; POINSARD, Cedric; WO2013/64681; (2013); 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 18368-57-5, name is 6-Methylpyridine-2-thiol. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 18368-57-5

Add 175mL DMF to the 500mL reaction flaskAnd (E)-1-iodo-3-(2,2-diphenyl-vinyl)benzene (38.78 g, 0.102 mol), protected with nitrogen,[1,1′-bis(diphenylphosphino)ferrocene]palladium dichloride dichloromethane complex (1.49 g,0.0018 mol), cesium carbonate (19.8 g, 0.061 mol) and dichloromethane 2 mL, added 5-methyl-pyridine-2-thiol (0.105 mol), heated to 80 C, and reacted for 16 hours until the reaction was complete.Rotate to remove DMF and cool to room temperature.Add 100 mL of ethyl acetate and 150 mL of water.Stir for 40 minutes, separate the organic phase, wash with salt water, layer,The organic phase was dried over sodium sulfate and filtered.Steam to dry,Flash column chromatography gave pale yellow (E)-2-((3-(2,2-diphenyl-vinyl)phenyl)thio)-5-methyl-pyridine, 27.96 g, yield 79% .

With the rapid development of chemical substances, we look forward to future research findings about 18368-57-5.

Reference:
Patent; Hao Huimin; (12 pag.)CN108484485; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 7379-35-3, 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. 7379-35-3, name is 4-Chloropyridine hydrochloride. A new synthetic method of this compound is introduced below.

tert-Butyl 2-(piperidin-4-yl)ethylcarbamate (0.2 g, 0.876 mmol), 4-chloropyridinium chloride (0.197 g, 1.314 mmol) and N-ethyl diisopropylamine (0.37 ml, 2.19 mmol) were refluxed in 2-propanol (10 ml) for 15 h. Saturated sodium hydrogen carbonate solution (20 ml) and ethyl acetate (50 ml) were added, the phases were separated and the aqueous phase was extracted with ethyl acetate (2.x.50 ml). The combined organic phases were dried over magnesium sulfate and concentrated to small volume under vacuum. The crude product was purified by column chromatography (silica gel) with ethyl acetate/dichloromethane/methanol/ammonia (25percent eq.) 400/100/50/1. Yield: 80 mg, 30percent

At the same time, in my other blogs, there are other synthetic methods of this type of compound,7379-35-3, 4-Chloropyridine hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; Gruenenthal GmbH; US2010/222324; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 41404-58-4, 2-Bromo-5-fluoropyridine, 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, 41404-58-4, blongs to pyridine-derivatives compound. category: pyridine-derivatives

(Related precendent, see Reider et al., Tett. Lett., 41, 2000, 4335-4338). Into a flask containing 2-Bromo-5-fluoro-pyridine (purchased from Aldrich, 2.5 g, 14.30 mmol, 1 eq) was dissolved toluene (143 mL, 0.1 M) and DMF (1.44 mL, 18.58 mmol, 1.3 eq, anhydrous) before being cooled to 78 C. under an inert atmosphere. nBuLi (17.1 mL, 17.14 mmol, 1 M hexanes) was added dropwise via an addition funnel over 15 min and allowed to stir for 90 min. To the mixture was added NaBH4 (1.08 g, 28.60 mmol, 2 eq) and the reaction allowed to warm up to room temp. The reaction was quenched with saturated NH4Cl and dissolved in EtOAc (300 mL). It was washed with water (2×100 mL) and brine (100 mL). The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. Flash column chromatography was used to purify the product using hexanes/Ethyl acetate (3/7) as eluent to furnish desired alcohol 148. 1H NMR (300 MHz) CDCl3 delta: partial 4.75 (s, 2H), 3.67 (bs, 1H). 19F NMR (300 MHz) CDCl3 delta: -129.80. MS: 127.96 (M+1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,41404-58-4, its application will become more common.

Reference:
Patent; GILEAD SCIENCES, INC.; US2007/72831; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1824-81-3, 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 1824-81-3 as follows.

An alkali trap, an equal pressure dropping funnel, a thermometer, and a mechanical stirrer were attached to a 1000 mL four-necked round bottom flask. (A) 2-amino-6-picoline (27.0 g 0.25 mol) and 48% HBr (125 mL 2.31 mol) were placed in this reaction vessel. The reaction vessel was immersed in an ice bath and cooled to 0 C. Br2 (37.5 mL 0.72 mol) was transferred to an equal pressure dropping funnel, The temperature of the reaction solution was kept at 0 C. and slowly dropped into the reaction vessel over 90 minutes while vigorously stirring with a mechanical stirrer. NaNO 2 (42.5 g 0.62 mol) was weighed and dissolved in about 100 mL of distilled water. This was transferred to an equal pressure dropping funnel,While stirring vigorously with a stirrer, it dripped over about 2 hours. At this time, care was taken that the temperature of the reaction solution did not exceed 10 C. In order to complete the reaction, NaNO 2 (2.50 g 0.036 mol) was dissolved in about 10 mL of distilled water and added, It was confirmed that nitrogen gas was not generated from the reaction vessel. While cooling in an ice bath, NaOH (95.0 g, 2.4 mol) was dissolved in about 300 mL of distilled water, after cooling sufficiently, it was gradually added to the solution for neutralization. At this time, care was taken that the temperature of the reaction solution did not exceed 20 C. The reaction mixture was extracted with Et 2 O (200 mL × 4) and the organic layer was collected. Anhydrous Na 2 SO 4 was added and dried, Upon concentration, a brown oily substance was obtained. This oily substance was distilled under reduced pressure in a rectifying tube, fractionated at 55 C. to 60 C. at a reduced pressure degree of 7.00 mmHg, A yellow oily substance was obtained. This material was stored at -40 C. Yield: 72% (32.0 g)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1824-81-3, its application will become more common.

Reference:
Patent; THE DOSHISHA; KODERA, MASAHITO; TSUJI, TOMOKAZU; (18 pag.)JP2017/197451; (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 754230-78-9, name is 3-(Benzyloxy)-5-bromopyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows. Safety of 3-(Benzyloxy)-5-bromopyridin-2-amine

Under argon, 200 g (0.72 mol) of 3-(benzyloxy)-5-bromopyridine-2-amine from Example 1 6A, 590 g (3.58 mol) of ethyl 2-chloroacetoacetate and 436 g of 3 Amolecular sieve were suspended in 6 1 of ethanol, and the suspension was stirred at reflux for 72 h. The reaction mixture was filtered oil through silica gel and concentrated. The residue was purified by silica gel chromatography (petroleum ether:ethyl acetate=9: 1, then 6:4) and the product fractions were concentrated. This gave 221 g (79% of theory) of the target compound.10595] LC-MS (Method 16): R=1.31 mm10596] MS (ESpos): mlz=389 (M+H)j0597] ?H-NMR (400 MHz, DMSO-d5): oe=1.36 (t, 3H), 2.58 (s, 3H), 4.32-4.41 (m, 2H), 5.33 (s, 2H), 7.28-7.32 (m, 1H), 7.36-7.47 (m, 3H), 7.49-7.54 (m, 2H), 8.98 (d, 1H).

With the rapid development of chemical substances, we look forward to future research findings about 754230-78-9.

Reference:
Patent; Bayer Pharma Aktiengesellschaft; VAKALOPOULOS, Alexandros; GROMOV, Alexey; FOLLMANN, Markus; BROCKSCHNIEDER, Damian; STASCH, Johannes-Peter; MARQUARDT, Tobias; TERSTEEGEN, Adrian; WUNDER, Frank; REDLICH, Gorden; LANG, Dieter; LI, Volkhart Min-Jian; (95 pag.)US2016/347770; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 573762-62-6 ,Some common heterocyclic compound, 573762-62-6, molecular formula is C7H4F3N3, 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.

General procedure: To a solution of compound 5 (50mg, 0.26mmol) and compound 11 (66mg, 0.26mmol) in DMA (0.5ml) was added thiophosgene (32mg, 0.26mmol) under N2. The reaction mixture was stirred for 16h at 60C. To this mixture were added MeOH (2ml) and 2M HCl (2ml), then the reaction mixture was reflux for 2h. After cooling to room temperature, the reaction mixture was poured into ice water (10ml) and extracted with EtOAc (10ml). The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by flash column chromatography on silics gel (EA/PE=1/1) to afford 4-(7-(6-cyano-5-(trifluoromethyl)pyridin-3-yl)-8-oxo-6-thioxo-5,7-diazaspiro[3.4]octan-5-yl)-2-fluoro-N-methylbenzamide (18) (51.3mg, 41%).

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. 573762-62-6, 5-Amino-3-(trifluoromethyl)picolinonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Pang, Xuehai; Wang, Yingwei; Chen, Yuanwei; Bioorganic and Medicinal Chemistry Letters; vol. 27; 12; (2017); p. 2803 – 2806;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 19337-97-4, 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. 19337-97-4, name is trans-3-(3-Pyridyl)acrylic acid, molecular formula is C8H7NO2, 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.

To a solution of (E)-3-(pyridin-3-yl)acrylic acid (0.40 g, 2.68 mmol, 1 eq) in DMF dry (4.0 mL), ammonium chloride (0.85 g, 16.10 mmol, 6 eq), HOBt (0.52 g, 3.86 mmol, 1.44 eq), EDCI (0.74 g, 4.20 mmol, 1.44 eq) and N-methylmorpholine (0.43 mL, 3.90 mmol, 1.44 eq) were subsequently added. The reaction was stirred at room temperature, under nitrogen for 3 h. After adding water, the reaction was filtered off through a neutral alumine oxide pad, washing with EtOAc/MeOH 9:1 (3 * 10 mL). The filtrate was evaporated and the residue was purified by column chromatography, using EtOAc/MeOH 9:1 as eluant to give 5 as white solid after crystallization with EtOAc (0.34 g, 85%). Mp 154-156 C. 1H NMR (300 MHz, CD3OD) delta 8.71 (d, J = 2.1 Hz, 1-H), 8.51 (dd, J = 4.9/1.5 Hz, 1-H), 8.05 (dt, J = 7.9/1.8 Hz, 1-H), 7.57 (d, J = 15.9 Hz, 1-H), 7.47 (dd, J = 7.9/4.9 Hz, 1-H), 6.77 (d, J = 15.9 Hz, 1-H); 13C NMR (75 MHz, CD3OD) delta 168.6, 149.5, 148.2, 137.1, 135.0, 131.5, 124.3, 123.1; MS (ESI) m/z 149 (M + H)+; IR (KBr) 3151, 3036, 2370, 1683, 1604, 1400, 980 cm-1. Anal. Calcd for C8H8N2O: C, 64.85; H, 5.44; N, 18.91. Found: C, 64.54; H, 5.12; N, 19.20.

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 19337-97-4, trans-3-(3-Pyridyl)acrylic acid.

Reference:
Article; Galli, Ubaldina; Mesenzani, Ornella; Coppo, Camilla; Sorba, Giovanni; Canonico, Pier Luigi; Tron, Gian Cesare; Genazzani, Armando A.; European Journal of Medicinal Chemistry; vol. 55; (2012); p. 58 – 66,9;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem