Pyridine-derivatives

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. 189281-66-1, name is Methyl 2,6-dichloro-5-fluoronicotinate, the common compound, a new synthetic route is introduced below. HPLC of Formula: C7H4Cl2FNO2

A mixture of 2,6-dichloro-5-fluoro-nicotinic acid methyl ester (1.00 g 4.46 mmol), trimethylboroxin (0.620 mL, 4.40 mmol), tetrakis(triphenylphosphine)palladium (0.500 g, 0.433 mmol) and potassium carbonate (1.50 g, 12.0 mmol) is heated at 110 0C overnight. The mixture is cooled to room temperature, diluted with water, and extracted with EtOAc. The combined organic phase is washed with water followed by brine, then dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue is purified by flash silica gel chromatography using a gradient of 0-30% EtOAc/heptane to provide 0.410 g (45.1%) of 2-chloro-5-fluoro-6-methyl-nicotinic acid methyl ester as a solid.

The synthetic route of 189281-66-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GINN, John David; MARSHALL, Daniel Richard; PROKOPOWICZ, Anthony S.; SCHYLER, Sabine; SIBLEY, Robert; TURNER, Michael Robert; WU, Di; WU, Frank; WO2010/126851; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 800401-68-7, 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.800401-68-7, name is 5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid, molecular formula is C8H5ClN2O2, molecular weight is 196.59, as common compound, the synthetic route is as follows.

Example 69: 5-Chloro-lH-pyrrolo[2,3-c]pyridine-2-carboxylic acid (2-oxo-l,2,3,4-tetrahydro- [1,5] naphthyridin-3-yl)amide; To a solution of 5-chloro-lH-pyrrolo[2,3-c]pyridine-2-carboxylic acid (Preparation 3, 50mg, 0.25mmol), EDCI (60mg, 0.31mmol) and HOBt monohydrate (40mg, 0.26mmol) in DMF (5mL) was added of 3-amino-3,4-dihydro-lH-[l,5]naphthyridin-2-one dihydrochloride (WO 03/074532, 60mg, 0.25mmol) and DIPEA (186muL, 1.07mmol) and the resulting solution stirred for 12h at rt. After concentration in vacuo the residue was partitioned between THF (5OmL) and carbonate buffer (10OmL, pH 10.5). The layers were separated and the aqueous phase extracted with THF (3x50mL). The combined THF fractions were washed with brine (5OmL), dried (MgSO4), filtered and concentrated. Addition of methanol (~2mL) led to the precipitation of the title compound, which was obtained as an off-white solid after filtration, delta? (ds DMSO): 3.23 (IH, dd), 3.38 (IH, dd), 4.95 (IH, m), 7.25 (3H, m), 7.80 (IH, s), 8.14 (IH, m), 8.61 (IH, s), 9.11 (IH, d), 10.50 (IH, s), 12.37 (IH, br s); m/z (ES+) = 342.03 [M-2HC1+H]+; RT = 2.40 min.

The chemical industry reduces the impact on the environment during synthesis 800401-68-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; PROSIDION LIMITED; WO2006/59164; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 77992-44-0, 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. 77992-44-0, name is (5-Bromopyridin-2-yl)hydrazine. A new synthetic method of this compound is introduced below.

A mixture of 369 mg (1.3 mmol) of the compound from Example 44A, 250 mg (1.3 mmol) of the compound from Example 10A and 46 mg (0.3 mmol) p-toluenesulfonic acid in 5 ml THF is reacted in a single mode microwave (Emrys Optimizer) at 170 C. for 30 min. After addition of 2 ml formic acid to the reaction solution, the solid which has precipitated out is filtered off, stirred with 3 ml of a 4 N solution of hydrogen chloride in dioxane, filtered off again, washed first with acetonitrile and then with diethyl ether and dried in vacuo.Yield: 163 mg (30% of th.)LC-MS (Method 10): Rt=1.06 min; MS (ESIpos): m/z=374 [M+H]+;1H-NMR (400 MHz, DMSO-d6): delta=8.65 (s, 1H), 8.45 (s, 1H), 8.38-8.23 (m, 2H), 8.19 (s, 1H), 8.15 (s, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,77992-44-0, (5-Bromopyridin-2-yl)hydrazine, and friends who are interested can also refer to it.

Reference:
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; US2010/305085; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 73998-95-5, name is (4,6-Dichloropyridin-3-yl)methanol, molecular formula is C6H5Cl2NO, 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. Quality Control of (4,6-Dichloropyridin-3-yl)methanol

Part II — Synthesis of 4,6-dichloropyridine-3-carbaldehyde [0231] (4,6-Dichloropyridin-3-yl)methanol (4.9 g, 28 mmol) was dissolved in CHC13 (100 mL). Mn02 (24 g, 280 mmol) was then added and the reaction mixture was stirred at 75 C for 12 hours. Next, the reaction was cooled to room temperature, filtered through Celite, and concentrated to give 4,6-dichloropyridine-3-carbaldehyde. Yield 2.9 g (90%>). LCMS (ESI): calc. C6H3C12N0 = 175; obs. M+H = low ionization.

With the rapid development of chemical substances, we look forward to future research findings about 73998-95-5.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LYCERA CORPORATION; AICHER, Thomas; BARR, Kenneth; LAPOINTE, Blair; SIMOV, Vladimir; STEIN, Karin; THOMAS, William; TOOGOOD, Peter; VAN HUIS, Chad; WHITE, Catherine; WO2013/169704; (2013); A2;,
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. 33252-30-1, name is 2-Chloroisonicotinonitrile, the common compound, a new synthetic route is introduced below. Quality Control of 2-Chloroisonicotinonitrile

General procedure: Aromatic or aliphatic nitriles (2 mmol) were dissolved in 5 ml of [bmim]HSO4 and the reaction mixture was heated at 60-65 C for 1-3 h. The progress of reaction was monitored by TLC. After completion of reaction, as checked by TLC, the reaction mixture was poured into water containing crushed ice. The product was precipitated out, filtered and dried. The yield of the final product was high (>90%) in all cases. All final products obtained were found sufficiently pure so it didn?t need further purification.The filtrate was concentrated under vacuum, washed with diethylether twice and concentrated under high vacuum. After proper drying under reduced pressure, approximately 95% ionic liquid was recovered from the reaction and compared with the original ionic liquid to check its authenticity. The efficiency of recovered ionic liquid in conversion of nitriles to acids was found unchanged in comparison to the original one and we reused it up to 5-6 cycles without any significant loss of its activity.

The synthetic route of 33252-30-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kumar, Satyanand; Dixit, Sandeep Kumar; Awasthi, Satish Kumar; Tetrahedron Letters; vol. 55; 28; (2014); p. 3802 – 3804;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 769-28-8, Adding some certain compound to certain chemical reactions, such as: 769-28-8, name is 4,6-Dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile,molecular formula is C8H8N2O, 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 769-28-8.

Example 6 3-(5-_ELhLI-2,4-dimgLhyl-6-oxo-1,6-dihydroMidin-3-yl)benzonitrile Step 1: 2-Chloro-3-cyano-4,6-dimethylpyridine: A stirred mixture of 3-cyano-4,6-dimethyl- 2-hydroxypyridine (4.35 g, 29.39 mmol) and phosphorous pentachloride (6.92 g, 33.21 mmol) is heated to 120C. The reaction mixture becomes clear and is stirred for an additional 1 hr. It is then poured onto ice/water (250 mL) and allowed to stand for 30 min. The solution is neutralized with sodium bicarbonate (pH 6) and extracted with dichloromethane (400 mL). The separated organic layer is dried, filtered and concentrated to yield 2-chloro-3-cyano-4,6- dimethylpyridine (4.60 g, 94% yield) as a tan solid containing ca 15% impurity. LC/MS: MS m/e = 167/169 (M + H) ; RT 2.98 min; NMR (CDCl3, 8 ppm) 7.08 (1H, s), 2.57 (3H, s), 2.55 (3H, s).

According to the analysis of related databases, 769-28-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AVENTIS PHARMACEUTICALS INC.; WO2005/97750; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 101990-69-6, Adding some certain compound to certain chemical reactions, such as: 101990-69-6, name is 2,6-Dichloropyridine-4-methanol,molecular formula is C6H5Cl2NO, 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 101990-69-6.

a) 4-(tert-Butyl-dimethyl-silanyloxymethyl)-2,6-dichloro-pyridine; A solution of 2,6-dichloropyridine-4-methanol (150 mg, 0.84 mmol), tert-butyl-chloro-dimethyl-silane (152 mg, 1.01 mmol) and imidazol (143 mg, 2.01 mmol) in 1 mL of N,N-dimethylformamide was stirred overnight at. The reaction mixture was concentrated in the rotatory evaporator, water was added and the slurry extracted with ethyl acetate. Chromatography on amino-modified silica gel (Merck HPTLC Silica Gel 60 NH2F254S) using heptane/ethylacetate (gradient 0 to 50% ethyl acetate) gave the pure title compound as a colorless solid (160 mg, 65%). MS ISP (m/e): 292.1 & 294.0 (100 & 97) [(M+H)+]. 1H NMR (CDCl3, 300 MHz): delta (ppm)=7.21 (s, 2H), 4.70 (s, 2H), 0.95 (s, 9H), 0.12 (6H).

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. 101990-69-6, 2,6-Dichloropyridine-4-methanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Baumann, Karlheinz; Flohr, Alexander; Goetschi, Erwin; Jacobsen, Helmut; Jolidon, Synese; Luebbers, Thomas; US2009/215759; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 89-00-9 , The common heterocyclic compound, 89-00-9, name is Pyridine-2,3-dicarboxylic acid, molecular formula is C7H5NO4, 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.

Pyridine-2,3-dicarboxylic acid (8.40 g, 50.30 mmol, 1 eq) was suspended in acetic anhydride (11.0 mL, 116.50 mmol, 2.3 eq) and the mixture was heated at 120 C, distilling 9.5 mL of acetic acid. After cooling at 100 C the acetamide (6.70 g, 113.60 mmol, 2.2 eq) was added portionwise in 5 min. The reaction was then heated at reflux for 2.5 h. After cooling at room temperature, the precipitate was filtered off and washed with water (2 * 12 mL) to give the desired product as grey solid after crystallization with EtOH/H2O 95:5 (3.46 g, 47%). Mp. 230-231 C. 1H NMR (300 MHz, DMSO-d6) delta 11.63 (br s, NH), 8.93 (d, J = 4.9 Hz, 1-H), 8.22 (d, J = 7.7 Hz, 1-H), 7.74 (dd, J = 7.6/4.9 Hz, 1-H). IR (KBr) 3483, 3189, 3100, 1735, 1704 cm-1.

The synthetic route of 89-00-9 has been constantly updated, and we look forward to future research findings.

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

Synthetic Route of 5350-93-6 ,Some common heterocyclic compound, 5350-93-6, molecular formula is C5H5ClN2, 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.

Bromine (24.86 g, 155.57 mmol) was added to a solution of6-chloropyridin-3-amine (20.00 g, 155.57 mmol) and sodium acetate (25.52 g, 311.14 mmol) in acetic acid(383 ml). The reaction mixture was stirred at room temperature for 1 hour. Acetic acidwas then evaporated. The residue was dissolved in EtOAc, washed with saturatedaqueous Na2C03, water and brine. The organic layer was dried over MgS04, filteredand evaporated, yielding 32.20 g of the desired product 49-a (99.8%). m/z = 206.96 (M+ It

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5350-93-6, its application will become more common.

Reference:
Patent; JANSSEN R&D IRELAND; TAHRI, Abdellah; JONCKERS, Tim Hugo Maria; RABOISSON, Pierre Jean-Marie Bernard; VENDEVILLE, Sandrine Marie Helene; HU, Lili; DEMIN, Samuel Dominique; Cooymans, Ludwig Paul; WO2013/186333; (2013); 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. 63071-09-0, name is 2-Hydroxymethyl-3-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 63071-09-0

2-Amino-4-furan-2-yl-6-(3-methyl-pyridin-2-yl-methoxy)-pyrimidine-5-carbonitrile From 2-amino-4-furan-2-yl-6-methanesulfinyl-pyrimidine-5-carbonitrile, (3-methyl-pyridin-2-yl)methanol and DBU in DME. ES-MS m/e (%): 308 (M+H+, 100).

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, 63071-09-0, 2-Hydroxymethyl-3-methylpyridine.

Reference:
Patent; Borroni, Edilio Maurizio; Huber-Trottmann, Gerda; Kilpatrick, Gavin John; Norcross, Roger David; US2001/27196; (2001); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem