Category: pyridine-derivatives

Synthetic Route of 149806-06-4 ,Some common heterocyclic compound, 149806-06-4, molecular formula is C6H4BrNO, 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.

Reagents: i) Methaneboronic acid, 16%; ii) Ethyl acrylate ; iii) NaOH, 35% yield for the last two steps.LC/MS data of 2805 – Calculated MW is 177; observed (the peak at 11.2 min, TIC): 178 [M+H].Gradient: 0-5 min: 5% ACN; 5-20 min: 5-10% ACN; 20-30 min: 10-98%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,149806-06-4, its application will become more common.

Reference:
Patent; TRUSTEES OF TUFTS COLLEGE; WO2008/16968; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 128071-75-0, 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.128071-75-0, name is 2-Bromonicotinaldehyde, molecular formula is C6H4BrNO, molecular weight is 186.01, as common compound, the synthetic route is as follows.

General procedure: To a solution of 2-bromobenzaldehyde (1a, 1 mmol) and 1H-pyrazol-5-amine (2a, 1.2 mmol) in DMF (5 mL) were added K2CO3 (2 mmol), CuI (0.2 mmol) and ethylenediamine(0.2 mmol). The mixture was stirred at 110 C until a complete conversion as indicated by TLC. It was cooled to room temperature and added with saturated brine, then extracted with ethyl acetate. The combined organic phase was concentrated under vacuum. The crude product was purified by columnchromatography eluting with petroleum ether/ethyl acetate (10:1) to give the desired product 3a. Products 3b-3ll were obtained in a similar manner.

Statistics shows that 128071-75-0 is playing an increasingly important role. we look forward to future research findings about 2-Bromonicotinaldehyde.

Reference:
Article; Gao, Lin; Song, Yunping; Zhang, Xinying; Guo, Shenghai; Fan, Xuesen; Tetrahedron Letters; vol. 55; 36; (2014); p. 4997 – 5002;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 105596-63-2, Adding some certain compound to certain chemical reactions, such as: 105596-63-2, name is 2-Methoxyisonicotinic acid,molecular formula is C7H7NO3, 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 105596-63-2.

LiAlH4 (1.9 g, 49 mmol) was added portionwise to a solution of 2-methoxy isonicotinic acid (5.0 g, 33 mmol) in tetrahydrofuran (40 mL) at 0 C. The reaction mixture was continuously stirred at 0 C for 1 h, then saturated sodium sulphate solution was added dropwise slowly. After filtration, the filtrate was extracted with ethyl acetate, and the organic layer was washed with brine, and concentrated under vacuum. The resulting residue was dissolved in dichloromethane (30 mL), and chromium trioxide pyridine (10.6 g, 49 mmol) was added. The resulting mixture was stirred at room temperature for 2 h, then poured onto the short silica gel column and eluted with ethyl acetate. The resulting solution was concentrated under vacuum to remove the solvent. The residue was purified by column chromatography (petroleum ether : ethyl acetate = 10:1) to afford the title compound (646 mg, 14 %). 1H NMR (CDCl3): delta 10.01 (1H, s), 8.36 (1H, d, J = 5.2 Hz), 7.29 (1H, dd, J = 1.2 Hz, 5.2 Hz), 7.14 (1H, d, J = 1.2 Hz), 3.99 (3H, s).

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. 105596-63-2, 2-Methoxyisonicotinic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Li, Yuliang; WANG, Huting; ZHU, Yan; WANG, Zhe; ZHANG, Hui; ZHAO, Ruiyu; HUANG, Yuanyuan; WANG, He; PENG, Yong; LUO, Hong; XIAO, Dengming; CAO, Shousong; HAN, Yongxin; EP2862571; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 86718-01-6 ,Some common heterocyclic compound, 86718-01-6, molecular formula is C9H8N2O2, 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.

Procedure A2 – Ester HydrolysisTo a solution of methyl imidazo[1 ,2-a]pyridine-7-carboxylate (3.Og, 17.04 mmol, 1.0 equiv) in EtOH (150 ml) was added 2M aqueous KOH (85 ml, 170 mmol, 10 equiv). The solution was heated for 30 min at 600C. After cooling to room temperature, the reaction was neutralized (HCI) and solvents were removed under reduced pressure. The residue was stirred in EtOH (2 x 100 ml) and filtered. The solvent was removed under reduced pressure and the resulting product was used in the next step without further purification. MS: [M+H]+ 163.

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. 86718-01-6, Methyl imidazo[1,2-a]pyridine-7-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; WO2009/47522; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 67346-74-1, 3-Ethynylpyridin-2-amine, 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, category: pyridine-derivatives, blongs to pyridine-derivatives compound. category: pyridine-derivatives

Reference Example 67 3-(3-(4-Butoxy-benzyl)-isoxazol-5-yl)-pyridin-2-ylamine; To a tetrahydrofuran (3 mL) solution of (4-butoxy-phenyl)-acetohydroximoyl chloride (150 mg, 0.619 mmol) described in Manufacturing Example 67-1-4 and 3-ethynyl-pyridin-2-ylamine (47 mg, 0.395 mmol) described in Manufacturing Example 1-2-3 was added triethylamine (216 muL, 1.55 mmol) at room temperature, which was stirred for 2 hours at 50° C. Water was added to the reaction solution at room temperature, which was then extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate. The solvent was evaporated under a reduced pressure. The residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=4:1-2:1) to obtain the title compound (27 mg, 14percent).1H-NMR Spectrum (CDCl3) delta (ppm): 0.95-0.99 (3H, m), 1.44-1.53 (2H, m), 1.72-1.79 (2H, m), 3.93-3.96 (2H, m), 4.00 (2H, s), 5.65 (2H, brs), 6.25 (1H, s),6.71-6.74 (1H, m), 6.86-6.88 (2H, m), 7.17-7.20 (2H, m), 7.72-7.75 (1H, m), 8.10-8.12(1H, m).

The synthetic route of 67346-74-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tanaka, Keigo; Yamamoto, Eiichi; Watanabe, Naoaki; US2009/82403; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 1227177-68-5, name is 3-Cyclopropyl-2-fluoropyridine. A new synthetic method of this compound is introduced below., Quality Control of 3-Cyclopropyl-2-fluoropyridine

STEP 3. N-(4-(3-CYCLOPROPYLPYRIDIN-2-YLOXY)PHENYL)BENZO[D]THIAZOL-2-AMINE To a solution of 4-(benzo[d]thiazol-2-ylamino)phenol (1.17 g, 4.81 mmol) in DMSO (40 mL) was added cesium carbonate (1.88 g, 5.78 mmol) and 3-cyclopropyl-2-fluoropyridine (660 mg, 4.81 mmol). The resulting mixture was heated to 125 C. for 16 h. After cooling to RT, the reaction mixture was diluted with EtOAc and washed with water and brine several times to remove DMSO. The aqueous layer was back extracted with EtOAc (3*) and the combined organic layer was dried (Na2SO4) and concentrated. The crude product was chromatographed through a Redi-Sep pre-packed silica gel column (120 g), eluding with a gradient of 0% to 30% EtOAc in hexane, to provide N-(4-(3-cyclopropylpyridin-2-yloxy)phenyl)benzo[d]thiazol-2-amine as tan solid. MS (ESI, pos. ion) m/z: 360.0 (M+1). IC50 (uM) +++++.

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, 1227177-68-5, 3-Cyclopropyl-2-fluoropyridine.

Reference:
Patent; AMEN INC.; US2010/125062; (2010); A1;,
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. 4487-59-6, name is 2-Bromo-5-nitropyridine, the common compound, a new synthetic route is introduced below. SDS of cas: 4487-59-6

-Bromo-5-nitropyridine (0.3 g, 1.48 mmol) was treated with piperazine (0.64 g, 7.89 mmol) in tetrahydrofuran (4 mL) and the reaction mixture was stirred for 30 minutes. Subsequently the reaction mixture was poured onto ice-cold water (25 mL) and extracted with ethyl acetate (25 mL). The organic layer was washed with brine and evaporated to furnish the product.

The synthetic route of 4487-59-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ORCHID RESEARCH LABORATORIES LIMITED.; US2007/167413; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 69045-84-7, 2,3-Dichloro-5-(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 2,3-Dichloro-5-(trifluoromethyl)pyridine, blongs to pyridine-derivatives compound. Safety of 2,3-Dichloro-5-(trifluoromethyl)pyridine

Example 6 : Preparation of 2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]-1-phenylethanamine; Preparation of 2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl-1-phenylethanone; To a suspension of 2.6 g (0.065 mol) of sodium hydride 60% in dimethoxyethane at room temperature is added 3.4 mL (0.029 mol) of acetophenone. After 45 min. , 5.55 mL ( 0.038 mol) of 2,3-dichloro-5-(trifluoromethyl)pyridine is added. After 25 min., the reaction mixture is poured over 100mL of hydrochloric acid 1N, extracted twice with 100mL of ethyl acetate. The organic phase is washed twice 100 mL of water, dried over magnesium sulfate, filtered and concentrated to provide 15g of crude material which is purified over a column of silica by using a mixture of heptane and ethyl acetate as eluent, to yield to 5.74 g of desired product 2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]-1-phenylethanone (74%). RMN 1H delta (ppm) 8,73 ; (1H, s) ; 7,95 (1H, s) ; 7,45 (2H, m) ; 7,42 (2H, m) ; 4,75 (2H, s).

The synthetic route of 69045-84-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer CropScience S.A.; EP1548007; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 72811-73-5, 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 72811-73-5, name is 4-(m-Tolylamino)pyridine-3-sulfonamide. This compound has unique chemical properties. The synthetic route is as follows.

Example 12; Preparation of torsemide [1]; A mixture of 4-m-tolylamino-3-pyridinesulfonamide [2], yellow powder with 98.0 % purity (0.5 % of 4-chloro-3-pyridinesulfonamide [4]) by HPLC (5.0 g, 19 mmol), 1 N aqueous solution of sodium hydroxide (19 mL, 19 mmol) and phenyl isopropylcarbamate (5.1 g, 23 mmol) was stirred at 90-100 C for 5 hours diluted with water (20 mL), cooled to 20-25 C, extracted with ter-butyl methyl ether (4 x 30 mL), neutralized with an 1 N aqueous solution of sulfuric acid at 20-25 C and stirred for 1 hour at 60-70 C. The precipitated solids were filtered off, washed on filter with hot water (20 mL) and acetone (20 mL) to give 5.6 g (85 %) of crude torsemide [1] 99.4 % purity (0.1 % of 4-m-tolylamino-3-pyridinesulfonamide [2]) by HPLC. A solution of sodium hydroxide (0.62 g, 16 mmol) in water (15 g) was added to a stirred suspension of crude torsemide [1] (5.0 g, 14 mmol) in water (45 g) at 20-30 C. The mixture was stirred at 20-30 C until a complete dissolution of the solids (pH 12.9) and charcoal SA (0.5 g) was added to the solution. After stirring for 2 hours, the obtained mixture was filtered off, cooled to 15-20 C and acidified to pH 4.6 with a 1 N solution of sulfuric acid in water (-28 mL, 28 mmol) at the same temperature. The obtained suspension was stirred for about 2 hours at 15-20 C and filtered. The solid was washed on the filter with water (50 g) and dried under reduced pressure at 55 i 5 C (water bath) to a constant weight to give 4.7 g of torsemide [1] as a white solid with 99.4 % purity by HPLC.

According to the analysis of related databases, 72811-73-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; FINETECH LABORATORIES LTD.; WO2003/97603; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 20260-53-1, 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. 20260-53-1, name is Nicotinoyl chloride hydrochloride. A new synthetic method of this compound is introduced below.

To a solution of 1 (50 mg, 0.071 mmol) in 354 ml of pyridine at room temperature was added nicotinoyl chloride hydrochloride (15 mg, 0.085 mmol) followed by triethylamine (23 ml, 0.170 mmol). After stirring for 1.5 h, 4-dimethylamino pyridine (8.6 mg, 0.071 mmol) was added. After stirring 5 h, additional triethylamine (23 ml, 0.170 mmol), 4-dimethylamino pyridine (8.6 mg, 0.071 mmol), and nicotinoyl chloride hydrochloride (15 mg, 0.085 mmol) was added along with a 50 ml pyridine rinse. After stirring 18 h the reaction was treated with 0.5 ml of saturated aqueous sodium bicarbonate and washed with methylene chloride (4×1 ml). The combined organic extracts were dried (Na2SO4), filtered, and concentrated in vacuo to a light brown oil. Chromatography (14 g of flash silica gel), eluting with ethyl acetate-hexanes (10:1) provided 49 mg (85%) of the free base as a white foam. The nicotinoate was dissolved in 1 ml of methylene chloride and treated with a 1.0 M solution of hydrogen chloride in diethyl ether (90 ml, 0.090 mmol). The clear, colorless solution was allowed to stand at room temperature for 5 min. Removal of the solvent in vacuo produced 51 mg of the title compound as a white foam: 500 MHz 1H NMR (CDCl3) d 8.94 (s, 1H), 8.78 (br s, 1H), 8.29 (d, 1H, J=7.0 Hz), 7.57 (br s, 1H), 7.38 (d, 2H, J=7.1 Hz), 7.30-7.16 (m, 5H), 7.10 (dd, 1H, J=8.4, 1.7 Hz), 6.88 (d, 1H, J=8.4 Hz), 6.71 (m, 1H), 5.80 (d, 1H, J=15 Hz), 5.74 (d, 1H, J=9.6 Hz), 5.56 (br s, 1H), 5.00 (d, 1H, J=9.6 Hz), 4.95 (t, 1H, J=8.9 Hz), 4.84 (d, 1H, J=9.8 Hz), 4.77-4.72 (m, 1H), 3.91 (s, 3H), 3.39 (dd, 1H, J=13, 8.2 Hz), 3.23-3.14 (m, 2H), 3.06 (dd, 1H, J=14, 7.6 Hz), 2.81-2.74 (m, 1H), 2.62-2.45 (m, 2H), 1.93 (ddd, 1H, J=14, 12, 4.8 Hz), 1.78-1.70 (m, 1H), 1.66-1.59 (m, 1H), 1.25 (s, 3H), 1.20 (d, 3H, J=7.0 Hz), 1.19 (s, 3H), 0.98 (d, 3H, J=6.7 Hz), 0.84 (d, 3H, J=6.5 Hz)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,20260-53-1, Nicotinoyl chloride hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; Eli Lilly and Company; Wayne State University; University of Hawaii; US6680311; (2004); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem