Category: pyridine-derivatives

Electric Literature of 116026-95-0 ,Some common heterocyclic compound, 116026-95-0, molecular formula is C11H14N2O3, 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.

(4-Formyl-pyridin-3-yl)-carbamic acid tert-butyl ester (100 mg) was dissolved in a hydrochloric acid-methanol solution (2.0 ml), and the solution was stirred under reflux for 30 min. The solvent was removed by distillation under the reduced pressure. 1-Chloro-propan-2-one (42 mg) dissolved in a 5 N aqueous sodium hydroxide solution (0.5 ml) was added to the residue, and the mixture was allowed to stand in an airtightly stoppered state for two days. The reaction mixture was neutralized with 10% hydrochloric acid, and dichloromethane was then added thereto for extraction. The dichloromethane layer was washed with water and saturated brine and was dried over magnesium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography with a chloroform-acetone system to give 2-methyl-[1,7]naphthyridin-3-ol (22 mg, yield 31%). 2-Methyl-[1,7]naphthyridin-3-ol (22 mg), 4-chloro-6,7-dimethoxyquinoline (92 mg), and 4-dimethylaminopyridine (50 mg) were suspended in 1,2-dichlorobenzene (1.5 ml), and the suspension was stirred at 140C for 8.5 hr. The reaction mixture was cooled to room temperature, and water was added thereto. The mixture was extracted with chloroform, and the chloroform layer was washed with water and saturated brine and was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography with a chloroform-methanol system to give the title compound (25 mg, yield 53%). 1H-NMR (CDCl3, 400 MHz): delta 2.76 (s, 3H), 4.01 (s, 3H), 4.06 (s, 3H), 6.54 (d, J = 5.6 Hz, 1H), 7.44 (s, 1H), 7.49 (s, 1H), 7.52 (d, J = 6.0 Hz, 1H), 7.61 (s, 1H), 8.57 (m, 2H), 9.45 (s, 1H) Mass spectrometric value (ESI-MS, m/z): 348 (M+1)+ (4-Formyl-pyridin-3-yl)-carbamic acid tert-butyl ester (100 mg) was dissolved in a hydrochloric acid-methanol solution (2.0 ml), and the solution was stirred under reflux for 30 min. The solvent was removed by distillation under the reduced pressure. 2-Chloro-1-phenyl-ethanone (70 mg) dissolved in a 5 N aqueous sodium hydroxide solution (0.6 ml) was then added to the residue, and the mixture was allowed to stand in an airtightly stoppered state for two days. The reaction solution was neutralized with 10% hydrochloric acid, and dichloromethane was then added thereto for extraction. The dichloromethane layer was washed with water and saturated brine and was dried over magnesium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography with a chloroform-acetone system to give 2-phenyl-[1,7]naphthyridin-3-ol (3 mg, yield 3%). 2-Phenyl-[1,7]naphthyridin-3-ol (3 mg), 4-chloro-6,7-dimethoxyquinoline (9 mg), and 4-dimethylaminopyridine (5 mg) were suspended in 1,2-dichlorobenzene (1.0 ml), and the suspension was stirred at 140C for 9 hr. The reaction mixture was cooled to room temperature, and water was added thereto. The mixture was extracted with chloroform, and the chloroform layer was washed with water and saturated brine and was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography with a chloroform-methanol system to give the title compound (3 mg, yield 54%). 1H-NMR (CDCl3, 400 MHz): delta 4.00 (s, 3H), 4.07 (s, 3H), 6.59 (d, J = 5.6 Hz, 1H), 7.39 (m, 4H), 7.61 (m, 2H), 7.86 (s, 1H), 7.98 (m, 2H), 8.50 (d, J = 5.6 Hz, 1H), 8.64 (d, J = 5.6 Hz, 1H) 9.62 (s, 1H) Mass spectrometric value (ESI-MS, m/z): 432 (M+Na)+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,116026-95-0, its application will become more common.

Reference:
Patent; KIRIN BEER KABUSHIKI KAISHA; EP1724268; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 65873-72-5, 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. 65873-72-5, name is 6-Methoxynicotinaldehyde, molecular formula is C7H7NO2, 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.

A stirred solution of 6-methoxy-3-pyridmecarboxaldehyde (0.45g, 3.3mMol) in 3N HCl(1OmL) was heated to 1000C for 30 minutes. Upon cooling, needle-like crystals developed. The crystals were collected via filtration to yield 17-2. 1H-NMR (CD3OD) delta 9.64 (s, IH), delta 8.17-8.16 (m, IH), delta 7.96-7.94 (m, IH), delta 6.58(d, IH).

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 65873-72-5, 6-Methoxynicotinaldehyde.

Reference:
Patent; MERCK & CO., INC.; WO2006/135627; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 87674-21-3, 1-(3-Fluoropyridin-4-yl)ethanone, 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, 87674-21-3, blongs to pyridine-derivatives compound. HPLC of Formula: C7H6FNO

To a stirred solution of 3-fluoro-4-acetylpyridine (5.3 g, 38.1 mmol) in glacial acetic acid (14 mL) and 48% hydrobromic acid (5.3 mL), bromine (2 mL, 38 mmol) in glacial acetic acid (5.3 mL) was added slowly and dropwise. After addition, the solution was stirred at 60 C. for 2.5 hour. This solution was cooled down and ethylacetate (70 mL) was added. After 30 minutes of stirring, the mixture was filtered and the solid was washed thoroughly with ethylacetate and dried. The title compound was obtained in 82% yield (9.4 g). 1H NMR (DMSO-d6/400 MHz) delta ppm 4.88 (s, 2 H) 7.83 (dd, 1 H) 8.62 (dd, 1 H) 8.81 (d, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,87674-21-3, its application will become more common.

Reference:
Patent; Pharmacia Italia S.p.A.; US2007/142415; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 917364-11-5, 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.917364-11-5, name is 5,6,7,8-Tetrahydroimidazo[1,2-a]pyridine-2-carboxylic acid, molecular formula is C8H10N2O2, molecular weight is 166.18, as common compound, the synthetic route is as follows.

Step (a) 5,6,7,8-Tetrahydroimidazo[l,2-alpha]pyridin-2-ylmethanol5,6,7,8-Tetrahydroimidazo[l,2-«]pyridine-2-carboxylic acid (230 mg, 1.38 mniol) was suspended in THF (2.287 mL) and borane-tetrahydrofyuran complex (6.92 mL, 6.92 mmol) was added. The mixture was heated at reflux for 3 h then cooled to room temperature over a period of two days, then heated to reflux for a further 16 h. Methanol (10 mL) was then added dropwise and the reaction stirred for one hour then concentrated in vacuo. The crude product was dissolved in methanol (5 mL) and passed through an SCX column washing with methanol (100 mL) and eluting with 3.5N ammoniacal methanol (75 mL). The basic organic layer was concentrated to give the sub-title compound as a yellow oil (134 mg). 1H NMR (400 MHz, CDCl3) delta 6.72 (s, IH), 4.55 (s, 2H), 3.91 (t, J = 5.9 Hz, 2H), 2.85 (t, J = 6.3 Hz, 2H), 2.01 – 1.87 (m, 4H).

Statistics shows that 917364-11-5 is playing an increasingly important role. we look forward to future research findings about 5,6,7,8-Tetrahydroimidazo[1,2-a]pyridine-2-carboxylic acid.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2008/84223; (2008); 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. 847406-13-7, name is Ethyl 1-(5-bromopyridin-3-yl)piperidine-4-carboxylate, the common compound, a new synthetic route is introduced below. SDS of cas: 847406-13-7

To a flask was added 7A (1. 00 G, 3.19 MMOL), DIOXANE (13 ML), triethyl AMINE (0. 97 g, 9. 58 mmol) and pinacol borane (0. 613 G., 4. 79’mmol). The mixture was degassed with N2 for 15 min and Pd2Cl2- (dppf) dcm (0.132 g, 0.16 mmol) was added. The flask was heated to 90C for 12 h and cooled to ambient temperature. The crude product was concen- rated in vacuo and purified by flash chromatography on silica gel eluting with 15% 7N methanolic ammonia/CM to provide the title compound (400 mg, 45%) 1H NMR (DMSO-d6, 400 MHz) 5 8.31 (d, J=2.73 Hz, 1H), 8.09 (m, 1H), 7.18 (m, 2H), 4.16 (dd, J=7.02, 14.04 Hz, 2H), 3.67 (m, 2H), 2. 85 (m, 2H), 2.46 (m, 1H), 2.05 (m, 2H), 1.89 (m, . 2H), 1.28 (t, J=7. 21 HZ,. 3H).

The synthetic route of 847406-13-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ICOS CORPORATION; WO2005/19200; (2005); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 877133-54-5, 4-Bromo-2,6-diethylpyridine, 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, SDS of cas: 877133-54-5, blongs to pyridine-derivatives compound. SDS of cas: 877133-54-5

-Bromo-2,6-diethylpyridine (2.9 g, 13.55 mmol), dichlorobis(trirhohenylphosphine)palladium (477 mg, 0.68 mmol) and copper(I) iodide (130 mg, 0.68 mmol) were placed in a vial and flushed with argon. Ethynyl(trimethyl)silane (2.34 mL, 16.9 mmol) and anhydrous lambdazetaiV-dimethylformamide (20 mL) were added followed by diisoproylamine (5.75 mL, 40.7 mmol). The reaction was divided into two 25 mL vials and irradiated in a microwave at 100 0C for 15 min. Water was added and the mixture was extracted with dichloromethane. The combined organic phases were concentrated in vacuo and purified by column chromatography, using a gradient of ethyl acetate (0 to 30%) in r°-heptane as the eluent, to give 1.64 g (63% yield) of the title compound: MS (ESI) m/z 111 [M+l]+.

The synthetic route of 877133-54-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTEX THERAPEUTICS LTD; WO2008/76046; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 89640-55-1, 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 89640-55-1, name is 3-Iodo-4-methoxypyridine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A mixture of the required iodide (1.0 mmol), Cu2O (0.10 g, 0.10 mmol), Cs2CO3 (0.65 g, 2.0 mmol), the required azole (2.0 mmol), and DMSO (0.5 mL) was stirred for 24 h at 110C. After cooling to room temperature, the mixture was diluted with AcOEt (10 mL) and filtered over Celite. Washing with AcOEt, removal of the solvent and purification by chromatography on silica gel (the eluent is given in the product description) led to the compound described below.

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 89640-55-1, 3-Iodo-4-methoxypyridine.

Reference:
Article; Hedidi, Madani; Erb, William; Bentabed-Ababsa, Ghenia; Chevallier, Floris; Picot, Laurent; Thiery, Valerie; Bach, Stephane; Ruchaud, Sandrine; Roisnel, Thierry; Dorcet, Vincent; Mongin, Florence; Tetrahedron; vol. 72; 41; (2016); p. 6467 – 6476;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 182924-36-3, 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. 182924-36-3, name is 5-(Bromomethyl)-2-chloropyridine, molecular formula is C6H5BrClN, 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.

1-(6-chloro-3-pyridyl)methyl-1,4,5,6-tetrahydropyrimidine [Compound 27] To an ice-cooled solution of 384 mg (4.6 mmol) of 1,4,5,6-tetrahydropyrimidine in 5 ml of acetonitrile was added 619 mg (3 mmol) of 5-bromomethyl-2-chloropyridine, and the mixture was stirred for 15 minutes. After removal of solvent under reduced pressure, 6 ml of the solution of 0.5N potassium hydroxide in ethanol was added to the residue. The insoluble matter was removed off by filtration, and the filtrate was concentrated under reduced pressure. The resulting residue was dissolved in toluene, and the solvent was removed again under reduced pressure. The resulting residue was purified by aminopropyl-coated silica gel (Chromatorex NH-type; Fuji Silysia Chemical Ltd.) column chromatography (eluent; dichloromethane_methanol=40:1) to give 221 mg (yield; 35.2%) of 1-(6-chloro-3-pyridyl)methyl-1,4,5,6-tetrahydropyrimidine as colorless oil.

According to the analysis of related databases, 182924-36-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Imoto, Masahiro; Iwanami, Tatsuya; Akabane, Minako; Tani, Yoshihiro; US2003/100769; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 582303-10-4, 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.582303-10-4, name is (2,6-Dimethylpyridin-3-yl)methanol, molecular formula is C8H11NO, molecular weight is 137.179, as common compound, the synthetic route is as follows.

A mixture of lambda/-[(2S)-5-hydroxy-2,3-dihydro-1 H-inden-2-yl]-2-propanesulfonamide (149 mg, 0.583 mmol, Description 3) and (2,6-dimethyl-3-pyridinyl)methanol (80 mg, 0.583 mmol) in dichloromethane (10 ml) was stirred under argon at room temperature. Triphenylphosphine (153 mg, 0.583 mmol) and DIAD (0.113 ml, 0.583 mmol) were then successively added. The resulting mixture was stirred at room temperature under argon for 16 hours. Then the reaction mixture was washed with water, dried over sodium sulphate, filtered and evaporated. The desired product was isolated by MDAP, concentrated to a small volume, and partitioned between dichloromethane and aqueous sodium hydrogen carbonate solution. The organic phase was dried over sodium sulphate, filtered and evaporated in vacuo to afford the desired compound as a free base. This was treated with ethereal hydrochloride / methanol to give the title compound as a white solid (92 mg).LC/MS (ES): Found 375 (ES+), retention time 1.67mins. C20H26N2O3S requires 374. 1 H-NMR (400MHz, DMSOd6): delta 8.34 (1 H, bs), 7.69 (1 H, bs), 7.46 (1 H, d, J=8.0Hz), 7.14 (1 H, d, J=8.0Hz), 6.94 (1 H, s), 6.84 (1 H, m), 5.19 (2H, s), 4.06 (1 H, m), 3.24-3.06 (3H, m), 2.87-2.74 (2H, m), 2.69 (3H, s), 2.60 (3H, s), 1.25 (6H, d, J=6.8Hz).

Statistics shows that 582303-10-4 is playing an increasingly important role. we look forward to future research findings about (2,6-Dimethylpyridin-3-yl)methanol.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/80637; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 872355-63-0, 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. 872355-63-0, name is Methyl 1H-pyrrolo[3,2-b]pyridine-5-carboxylate. A new synthetic method of this compound is introduced below.

To the methanol (1OmL) and water (10 mL) suspension of lH-pyrrolo[3,2-b]pyridine- 5-carboxylic acid methyl ester (0.54 g) was added sodium hydroxide (0.37 g) . The reaction was heated at 70 0C for 2 h. The reaction mixture was concentrated and the residue obtained was redissolved in water. The aqueous solution was acidified with cone, hydrochloric acid to pH 2. The solid thus separated was filtered, washed with water and dried under high vacuum. It was used as such for the next step without any purification (Yield: 0.49 g, Rf: 0.213 min, Condition B, M+H+: 163). EPO

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,872355-63-0, its application will become more common.

Reference:
Patent; SCIOS, INC.; WO2006/112828; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem