Category: pyridine-derivatives

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.188554-13-4, name is 2-Hydroxyisonicotinaldehyde, molecular formula is C6H5NO2, molecular weight is 123.11, as common compound, the synthetic route is as follows.COA of Formula: C6H5NO2

(R)-2-(2-Hydroxy-pyridin-4-yl)-thiazolidine-4-carboxylic acidTo a solution of L-cysteine hydrochloride (402.9 mg, 2.56 mmol) in distilled water (4 mL), potassium acetate (281.7 mg, 2.87 mmol) was added. Once the solids went into solution, methanol (4 mL) was added followed by 2-hydroxy-pyridine-4-carbaldehyde (376.4 mg, 3.06 mmol). Precipitate crashed out of solution within one hour, and the reaction was stirred at ambient temperature overnight. The solvent was removed to give the crude product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,188554-13-4, 2-Hydroxyisonicotinaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; GENELABS TECHNOLOGIES, INC.; WO2008/64218; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1721-26-2, 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. 1721-26-2, name is Ethyl 2-methylnicotinate, molecular formula is C9H11NO2, 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 A. 3-Hydroxymethyl-2-methyl-pyridine Prepared according to a slightly modified procedure of I. M. Bell et al., J. Med. Chem. 41, 2146-2163 (1998). To a stirred solution of ethyl 2-methylnicotinate (2.0 g, 12.1 mmol) in tetrahydrofuran (40 mL) cooled to 0° C. was slowly added a 1 M solution of diisobutyl aluminum hydride in tetrahydrofuran (30 mL, 30 mmol). After 5 minutes, the reaction was quenched with saturated aqueous sodium bicarbonate and saturated aqueous sodium potassium tartrate. The aqueous phase was repeatedly extracted with chloroform. The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give 2.5 g of the crude title compound as a yellow oil. The crude material was used as such in the next step. 1H NMR (DMSO-d6, 400 MHz): delta2.40 (s, 3H), 4.49 (d, 2H), 5.23 (t, 1H), 7.16-7.19 (m, 1H), 7.67-7.69 (m, 1H), 8.28-8.31 (m, 1H). MS [(+)APCI, m/z]: 124 [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 1721-26-2, Ethyl 2-methylnicotinate.

Reference:
Patent; Wyeth; US2003/55047; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 55314-16-4, 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 55314-16-4 as follows.

4.83 g of 3-dimethylamino-1-pyridin-3-yl-prop-2-en-1-one (30.0 mmol, 1.0 equiv), 4.68 g of methyl propionylacetate (36.0 mmol, 1.2 equiv.), 4.62 g of ammonium acetate (60.0 mmol, 0.2 equiv.), 2.25 g of cerium (III) chloride heptahydrate (6.0 mmol, 0.2 equiv.), 900 mg of sodium iodide (6.0 mmol, 0.2 equiv.) and 30 ml of isopropanol were mixed and refluxed overnight under stirring. The reaction solution was cooled and filtered, and the filtrate was concentrated and subjected to column chromatography, eluting with ethyl acetate/petroleum ether (1:50) to obtain 4.5 g of methyl 6-ethyl- [2,3′] bipyridyl-5-carboxylate as a yellow solid, 61.9%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,55314-16-4, its application will become more common.

Reference:
Patent; Shenyang Sunshine Pharmaceutical Co., Ltd.; ZHOU, Yunlong; CAI, Suixiong; WANG, Guangfeng; JIAO, Lingling; MIN, Ping; JING, Yu; GUO, Ming; (48 pag.)EP3287456; (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. 128071-98-7, name is 4-Bromo-2-fluoropyridine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 4-Bromo-2-fluoropyridine

LiHMDS (1M in toluene, 17.6 mL, 17.6 mmol, 3.1 eq) is added dropwise to a cold (-5 C.) mixture of 4-bromo-2-fluoro-pyridine [Marsais, F. et al, Journal of Organic Chemistry, (1992), 57, 565-573] (1 g, 5.7 mmol), cyclopropanecarbonitrile (1.25 mL, 17 mmol, 3 eq), 4 A molecular sieves and toluene (20 mL). The reaction mixture is allowed to warm to rt, stirred for 16 h, poured into H2O and filtered. The filtrate is diluted with EtOAc/H2O and extracted with EtOAc. The organic phase is washed with H2O and brine, dried (Na2SO4), filtered and concentrated. The residue is purified by silica gel column chromatography (Hex/EtOAc, 9:1), to afford 620 mg of the title compound as a white solid: ESI-MS: 223.1/225.1 [M+H]+; tR=4.22 min (System 1); TLC: Rf=0.25 (Hex/EtOAc, 9:1).

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, 128071-98-7, 4-Bromo-2-fluoropyridine.

Reference:
Patent; Novartis AG; US2009/163469; (2009); A1;,
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.202348-55-8, name is 6-Methylimidazo[1,2-a]pyridine-2-carbaldehyde, molecular formula is C9H8N2O, molecular weight is 160.1726, as common compound, the synthetic route is as follows.Computed Properties of C9H8N2O

A solution of 3-methoxy-/V-((6-methylimidazo[1 ,2-a]pyridin-2-yl)methylene)aniline in ethanol was prepared by heating a solution of 6-methylimidazo[1 ,2-a]pyridine-2-carbaldehyde (0.160 g; 0.999 mmol) and 3-methoxyaniline (0.1 13 mL; 1.009 mmol) in ethanol (0.5 mL) at 65 C for 24 h. The formation of the imine was quantitative and the solution was used without further purification. ESI/APCI (+): 266 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,202348-55-8, 6-Methylimidazo[1,2-a]pyridine-2-carbaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; KATHOLIEKE UNIVERSITEIT LEUVEN; BARDIOT, Dorothee; CARLENS, Gunter; DALLMEIER, Kai; KAPTEIN, Suzanne; McNAUGHTON, Michael; MARCHAND, Arnaud; NEYTS, Johan; SMETS, Wim; WO2013/45516; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 609-71-2 ,Some common heterocyclic compound, 609-71-2, molecular formula is C6H5NO3, 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 155A 1-butyl-2-oxo-1,2-dihydropyridine-3-carboxylic acid To a solution of 2-hydroxy-nicotinic acid (0.50 g, 3.59 mmol) and potassium hydroxide (0.40 g, 7.13 mmol) in 4:1 methanol: water (6 mL) at room temperature, was added 1-iodobutane (0.74 mL, 6.42 mmol). This solution was heated at 60 C. for 30 minutes, then cooled to room temperature and diluted with water and 1N HCl. The resulting solid was filtered and dried to give the title compound (0.27 g, 39%). MS (DCI/NH3) m/z 196 (M+H)+; 1H NMR (300 MHz, DMSO-d6) delta 0.91 (m, 3H) 1.30 (m, 2H) 1.69 (m, 2H) 4.10 (m, 2H) 6.73 (m, 1H) 8.27 (dd, J=6.62, 1.84 Hz, 1H) 8.38 (dd, J=7.35, 2.21 Hz, 1H) 14.68 (s, 1H).

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. 609-71-2, 2-Oxo-1,2-dihydropyridine-3-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Pratt, John K.; Betebenner, David A.; Donner, Pamela L.; Green, Brian E.; Kempf, Dale J.; McDaniel, Keith F.; Maring, Clarence J.; Stoll, Vincent S.; Zhang, Rong; US2004/162285; (2004); 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 58530-53-3, name is 2,4-Dibromopyridine. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 2,4-Dibromopyridine

Compound 3a (1 g, 4.22 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate 8a (1.305 g, 4.22 mmol), tetrakis(triphenylphosphine)palladium (487 mg, 0.422 mmol) and sodium carbonate (894.85 mg, 8.44 mmol) were dissolved in 14 mL of a mixed solvent of toluene, ethanol and water (V/V/V=4:2:1), then the reaction solution was warmed up to 100C and reacted under microwave for 1 hours. The reaction solution was cooled to room temperature, filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography with elution system B to obtain the title compound 8b (220 mg, yield: 15.36%).

With the rapid development of chemical substances, we look forward to future research findings about 58530-53-3.

Reference:
Patent; Jiangsu Hengrui Medicine Co., Ltd.; Shanghai Hengrui Pharmaceutical Co., Ltd.; YU, Shanghai; YANG, Fanglong; YAN, Jingjing; WU, Xiao; HE, Feng; TAO, Weikang; (116 pag.)EP3527570; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 873107-98-3, 5-Iodo-2-(trifluoromethyl)pyridine, 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, Safety of 5-Iodo-2-(trifluoromethyl)pyridine, blongs to pyridine-derivatives compound. Safety of 5-Iodo-2-(trifluoromethyl)pyridine

A mixture of 5-iodo-2-(trifluoromethyl)pyridine (0.1 1 g, 0.39 mmol), Intermediate 21 (100 mg, 0.33 mmol), Pd2(dba)3 (15 mg, 0.02 mmol), xantphos (9.4 mg, 0.02 mmol) and Cs2C03 (0.21 g, 0.65 mmol) in anhydrous dioxane (10 mL) was heated at 100C for 19 hrs. The reaction mixture was cooled to ambient temperature, concentrated in vacuo and the crude product purified by chromatography on the Biotage Companion (40 g column, 0 to 60%, EtOAc in isohexane) and the further purified by chromatography on the Biotage Companion (12 g column, 0 to 5% methanol in DCM) to afford the title compound as a solid (45 mg). LCMS (Method A): Two peaks at 2.25 min and 2.49 min, 453/455 [M+H]+. 1H NMR (400 MHz, DMSO-d6) 8.17-8.10 (m, 1 .59 H), 8.06 (s, 0.91 H), 8.03-7.95 (m, 0.32 H), 7.95-7.86 (m, 0.62 H), 7.83 (d, 0.08 H), 7.79 (d, 0.32 H), 7.74-7.64 (m, 0.81 H), 7.54 (d, 0.67 H), 7.50-7.40 (m, 1 .07 H), 7.36 (d, 0.12 H), 7.16-7.07 (m, 1 .03 H), 6.92-6.81 (m, 0.84 H), 6.81 -6.72 (m, 0.46 H), 6.70 (bdd, 0.08 H), 6.40 (bm, 0.08 H), 4.62 (bm, 0.32 H), 4.43 (bm, 0.15 H), 3.58 (bm, 0.09 H), 3.35 (bm, 0.52 H), 3.19 (bm, 0.42 H), 3.01 (bm, 0.08 H), 2.88 (s, 2.39 H), 2.83 (s, 0.62 H), 2.68 (bm, 2.12 H), 1.78- 1 .52 (bm, 1.21 H), 1.35 (bm, 0.15 H), 0.97 (m, 1.98 H), 0.89 (t, 0.39 H), 0.51 (t, 0.56 H).

The synthetic route of 873107-98-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; C4X DISCOVERY LIMITED; BLANEY, Emma Louise; MARTIN, Barrie Phillip; NOWAK, Thorsten; WATSON, Martin John; (212 pag.)WO2016/34882; (2016); A1;,
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.1060808-92-5, name is 6-Bromo-4-chloronicotinic acid, molecular formula is C6H3BrClNO2, molecular weight is 236.45, as common compound, the synthetic route is as follows.category: pyridine-derivatives

To 6-bromo-4-chloro-pyridine-3-carboxylic acid (205 mg, 0.865 mmol), (3-fluoro-5-isobutoxy-phenyl)boronic acid (184 mg, 0.865 mmol), and palladium;triphenylphosphane (30.0 mg, 0.0260 mmol) in dioxane (4 mL) was added solution of potassium carbonate (1.73 mL of 2 M, 3.46 mmol) under an atmosphere of nitrogen and the reaction mixture was stirred at 80 C. for 10 h. The reaction mixture was concentrated under reduced pressure, partitioned between water (15 mL) and EtOAc (15 mL). The aqueous layer was acidified with HCl and washed with EtOAc (3×15 mL). The combined organic layers was washed with brine (1×25 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. The solid obtained was washed with hexanes to give 4-chloro-6-(3-fluoro-5-isobutoxy-phenyl)pyridine-3-carboxylic acid (232 mg, 83%) as a tan solid. ESI-MS m/z calc. 323.07245. found 324.1 (M+1)+. Retention time: 0.74 minutes.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1060808-92-5, 6-Bromo-4-chloronicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; Miller, Mark Thomas; Anderson, Corey; Arumugam, Vijayalaksmi; Bear, Brian Richard; Binch, Hayley Marie; Clemens, Jeremy J.; Cleveland, Thomas; Conroy, Erica; Coon, Timothy Richard; Frieman, Bryan A.; Grootenhuis, Peter Diederik Jan; Gross, Raymond Stanley; Hadida-Ruah, Sara Sabina; Haripada, Khatuya; Joshi, Pramod Virupax; Krenitsky, Paul John; Lin, Chun-Chieh; Marelius, Gulin Erdgogan; Melillo, Vito; McCartney, Jason; Nicholls, Georgia McGaughey; Pierre, Fabrice Jean Denis; Silina, Alina; Termin, Andreas P.; Uy, Johnny; Zhou, Jinglan; (590 pag.)US2016/95858; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 69872-17-9, 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 69872-17-9, name is 4-Bromo-1H-pyrrolo[2,3-c]pyridine. This compound has unique chemical properties. The synthetic route is as follows.

To a mixture of compound 4-bromo-1H-pyrrolo[2,3-c]pyridine (D16) (20.4 g), Zn(CN)2 (12.2 g) and Zn dust (1.4 g) in DMF (300 mL) was added Pd(dppf)CI2 (8.5 g). The reaction mixture was heated to 120 0C and stirred at that temperature for 2 h. The mixture was diluted with water, extracted with EtOAc. The organic layers were washed with water and brine, dried over anhydrous Na2SO4 , evaporated and purified on column chromatography to afford 1H-pyrrolo[2,3-c]pyridine-4-carbonitrile (D17) as white solid (3.9 g). deltaH (DMSO-d6, 400MHz): 6.69 (1 H, d), 7.93 (1 H, d), 8.57 (1 H, s), 9.01 (1 H, s), 12.30 (1H, s); MS (ES): C8H5N3 requires 143; found 144.0 (M+H+)

According to the analysis of related databases, 69872-17-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; LIN, Xichen; MENG, Qinghua; ZHANG, Haibo; LI, Chengyong; WO2010/145201; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem