Category: pyridine-derivatives

Reference of 745784-04-7 , The common heterocyclic compound, 745784-04-7, name is 3,5-Difluoropicolinic acid, molecular formula is C6H3F2NO2, 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.

Intermediate 9: (3,5-difluoro-2-py; 3,5-difluoro-2-pyridinecarboxylic acid (ALFAAESAR , 300 mg, 1.886 mmol) was dissolved in tetrahydrofuran (THF) (10 mL). A/,A/-diethylethanamine (FLUKA, 0.549 mL, 3.96 mmol) was added and mixture was cooled to -10C (ice in acetone). Isobutyl chloroformate (0.269 mL, 2.074 mmol, FLUKA) was added dropwise. Reaction was stirred 20 min at – 10C. Mixture was filtered into a previously prepared solution of sodium borohydride (ALDRICH, 214 mg, 5.66 mmol) in 2 mL of water at 0C and was stirred at 0C for 45 min. HCI (1 N, aq) was added slowly until neutral pH. Aqueous mixture was partitioned with DCM (3x15ml). Organic layer was dried over Na2S04 (anh), filtered and concentrated. Residue was purified by silica gel chromatography using a linear gradient of DCM/MeOH to yield title compound (3,5-difluoro-2-pyridinyl)methanol (1 16 mg, 0.799 mmol, 42.4% yield). 1 H NMR (400 MHz, DMSO-cfe) delta ppm: 8.44-8.45 (s, 1 H), 7.88-7.93 (m, 1 H), 5.35 (t, 1 H), 4.56-4.58 (m, 2H). [ES+MS] m/z 146 (MH+).

The synthetic route of 745784-04-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; CASTRO PICHEL, Julia; FERNANDEZ MENENDEZ, Raquel; FERNANDEZ VELANDO, Esther Pilar; GONZALEZ DEL VALLE, Silvia; MALLO-RUBIO, Araceli; WO2012/49161; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 54221-96-4 , The common heterocyclic compound, 54221-96-4, name is 6-Methoxypicolinaldehyde, molecular formula is C7H7NO2, 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.

The general procedure for the synthesis of the 3-aminoindolizine derivatives 1a-e, 6a-g, and uncyclized product 8a-c is described below: To a reaction mixture of cyano substrate 3 (2.0 mmol), 2-carbonyl pyridine derivative (2.0 mmol), and piperidinium acetate (15 mg, 0.10 mmol) in toluene (6 ml), was added diethyl 1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate (9) (Hantzsch ester, 557 mg, 2.2 mmol) in one portion at room temperature. The resulting mixture was degassed with a stream of nitrogen and then stirred at 105 °C for 3 h. After cooling to room temperature, a minimum amount (ca 0.3-0.5 mL) of DMSO was added to the reaction mixture and the resulting solution was directly loaded to a silica gel column and purified by column chromatography using Teledyne Isco Combiflash system.

The synthetic route of 54221-96-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Li, Lianhai; Chua, Waepril Kimberly S.; Tetrahedron Letters; vol. 52; 12; (2011); p. 1392 – 1394;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1658-42-0, Adding some certain compound to certain chemical reactions, such as: 1658-42-0, name is Methyl 2-(pyridin-2-yl)acetate,molecular formula is C8H9NO2, 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 1658-42-0.

General procedure: A mixture of phenylethynylbromide (1a) (1.0 mmol), ethyl2-pyridylacetate (2a) (0.6 mmol), AgNO3 (34.0 mg, 0.2 mmol, 0.2 equiv.), DABCO(70.0 mg, 1.0 mmol, 1.0 equiv.) in DMSO (3.0 mL) in a test tube (25 mL)equipped with a magnetic stirring bar. The mixture was stirred at 100 oCfor 12 h. After the reaction was completed, the mixture was washed with brineand extracted with ethyl acetate. The organic layer was dried (MgSO4),concentrated in vacuum and purified by flash silica gel chromatography usingpetroleum ether/ethyl acetate 10:1 to give the desired products.

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. 1658-42-0, Methyl 2-(pyridin-2-yl)acetate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zeng, Wei; Wu, Wanqing; Jiang, Huanfeng; Sun, Yadong; Chen, Zhengwang; Tetrahedron Letters; vol. 54; 35; (2013); p. 4605 – 4609;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 82205-58-1, 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. 82205-58-1, name is 1-(5-Nitropyridin-2-yl)piperazine, molecular formula is C9H12N4O2, 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.

(General acetylation/sulphonylation procedure). Compound 3b (208 mg, 1 mmol), acetyl chloride (79 mul, 1.1 mmol) and PS-NMM (100 mg) in CH2Cl2 (5 mL) were stirred for 16 h. After adding PS-Trisamine (150 mg) to the reaction mixture was left to stir for a further 2 h, filtered and concentrated in vacuum to afford a yellow solid: 250 mg (90%) yield.

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 82205-58-1, 1-(5-Nitropyridin-2-yl)piperazine.

Reference:
Article; Spencer, John; Patel, Hiren; Callear, Samantha K.; Coles, Simon J.; Deadman, John J.; Tetrahedron Letters; vol. 52; 45; (2011); p. 5905 – 5909;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 917023-06-4, 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. 917023-06-4, name is Methyl 2-(5-bromopyridin-2-yl)acetate. A new synthetic method of this compound is introduced below.

A single-necked round-bottomed flask was charged with Compound 2 (1.80g, 7.82mmol), 3-fluorobenzylamine (2.94g, 23.5mmol), and anhydrous anisole 05g). The reaction was stirred at 150C until reaction was complete LCMS (~23h) and then allowed to cool to near RT. Crystals of the desired product, Compound 3, formed during the cooling process and were collected by filtration and washed with toluene. Compound 3 was obtained as colorless crystalline solid (1.59g, 63% yield) and characterized by 1H NMR (400MHz, DMSO-d6): 3 ,69 (s, 2H), 4,30 (d, 2H), 7.0-7.15 (m, 3H), 7.3-7.4 (m, 2H), 7.99 (dd, 1H), 8.61 (fine d, 1H), 8.66 (br t, 1H),

At the same time, in my other blogs, there are other synthetic methods of this type of compound,917023-06-4, Methyl 2-(5-bromopyridin-2-yl)acetate, and friends who are interested can also refer to it.

Reference:
Patent; ATHENEX, INC.; SMOLINSKI, Michael P.; NASIEF ABDEL-SAYED, Nader N.; HANGAUER, JR., David G.; (197 pag.)WO2018/31988; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 552331-00-7, 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. 552331-00-7, name is 4-Iodopyridin-2-amine. A new synthetic method of this compound is introduced below.

Reference Example 42; 3-(2-aminopyridin-4-yl)-5-phenyl-1,3-oxazolidin-2-oneTo a solution of 4-iodopyridin-2-amine (2.0 g, 9.09 mmol), 5-phenyl-1,3-oxazolidin-2-one (1.7 g, 10.5 mmol) obtained in Reference Example 41 and potassium carbonate (2.5 g, 18.2 mmol) in 1,4-dioxane (30 mL) were added copper iodide (173 mg, 909 mumol) and N,N’-dimethylethylenediamine (80 mg, 909 mumol) at room temperature, and the mixture was heated under reflux for 16 hr under an argon stream. The solid was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate) to give the title compound (1.78 g, yield 77%) as crystals.melting point 155-156 C. (ethyl acetate-hexane)1H-NMR (CDCl3) delta: 3.90 (1H, dd, J=9.0, 7.5 Hz), 4.35 (1H, t, J=9.0 Hz), 4.49 (2H, br s), 5.64 (1H, t, J=7.5 Hz), 6.67 (1H, dd, J=6.0, 2.1 Hz), 6.93 (1H, d, J=2.1 Hz), 7.34-7.50 (5H, m), 8.00 (1H, d, J=6.0 Hz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,552331-00-7, 4-Iodopyridin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; Takeda Pharmaceutical Company Limited; US2011/39893; (2011); 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. 183610-70-0, name is 2-Amino-3-(trifluoromethyl)pyridine. A new synthetic method of this compound is introduced below., name: 2-Amino-3-(trifluoromethyl)pyridine

To a solution of 5.37 g (32.8 mmol) of 3-trifluoromethyl-pyridin-2-ylamine (Fluorochem Ltd., Derbyshire, United Kingdom) in 100 ml of dry CH3CN, 6.45 g of NBS are added in 4 equal portions over a period of 1 h at 0-50C under argon. The cooling bath is removed and stirring is continued for 3 h. The solvent is evaporated under vacuum, the residue is dissolved in EtOAc and washed with water and brine. The organic phase is dried over Na2SO4 and evaporated. The title compound is a red-dish-yellow oil which is used after drying in the dark for 5 h at RT and under high vacuum in the next step without further purification. ES-MS (M+1 ): = 239; 241 ; HPLC: tR = 5.501 min. Example 1.4 1 -(2-Methoxy-pyridin-3-yl)-3-methyl-8-(6-methylamino-pyridin-3-yl)-1 ,3-dihydro- imidazo[4,5-c]quinolin-2-one

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, 183610-70-0, 2-Amino-3-(trifluoromethyl)pyridine.

Reference:
Patent; NOVARTIS AG; FURET, Pascal; IMBACH, Patricia; MAH, Robert; STAUFFER, Frederic; WO2010/139747; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 144100-07-2 ,Some common heterocyclic compound, 144100-07-2, molecular formula is C5H3BrFN, 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.

A mixture of 2-bromo-6-fluoropyridine (212 mg, 1.21 mmol), (R)-1-(tetrahydro-2H- pyran-4-yl)ethanamine (200 mg, 1.21 mmol), DIPEA (187 mg, 1.45 mmol) and DMSO (3 ml_) was heated in a sealed tube at 90 °C for 18 hrs. The reaction mixture was allowed to cool to room temperature, poured into water (30 ml_) and stirred for 20 min. The mixture was extracted with EtOAc (3x 15 ml_). The combined organic layers were washed with brine (100 ml_) and concentrated to dryness under reduced pressure. The residue was purified by column chromatography [silica gel] providing (R)-6-bromo-N-(1- (tetrahydro-2H-pyran-4-yl)ethyl)pyridin-2-amine (290 mg). LCMS (m/z): 285.0/286.9 [M+H]+; Rt = 0.91 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,144100-07-2, its application will become more common.

Reference:
Patent; NOVARTIS AG; BARSANTI, Paul A.; HU, Cheng; JIN, Xianming; NG, Simon C.; PFISTER, Keith B.; SENDZIK, Martin; SUTTON, James; WO2012/101063; (2012); 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. 1121-76-2, name is 4-Chloropyridine 1-oxide. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 4-Chloropyridine 1-oxide

4-Chloropyridine-N-oxide (3.0 g, 23 mmol), 4-trifluoromethylphenylboronic acid (6.57 g, 34.6 mmol), K2CO3 (4.8 g, 35 mmol) and PdCl2(dppf) (470 mg, 0.57 mmol) were stirred in DMSO (40 mL) under vacuum for 30 min. The flask was flushed with nitrogen, and the mixture was heated to 80 C. for 10 min. Upon cooling, the mixture was diluted with methylene chloride and washed with 5% lithium chloride solution (5*), dried, concentrated, and the residue was purified by flash column chromatography (40 g ISCO column eluting with methylene chloride and a methanol/ammonia mixture (10:1); gradient 100% methylene chloride to 80% methylene chloride over 30 min at 40 mL/min) to provide the title compound (1.90 g, 34%) as a tan solid: ESI MS m/z 240 [M+H]+.

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, 1121-76-2, 4-Chloropyridine 1-oxide.

Reference:
Patent; ALBANY MOLECULAR RESEARCH, INC.; US2012/157460; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 33252-64-1, 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. 33252-64-1, name is 3-Nitro-5-(trifluoromethyl)pyridin-2(1H)-one. A new synthetic method of this compound is introduced below.

3-Nitro-5-(trifluoromethyl)pyridin-2-ol (31.00 g, 149 mmol) was dissolved in acetonitrile (250 ml) to give a dark brown solution. Phosphorus(V) oxybromide (85 g, 298 mmol) was added and the mixture was heated at reflux for 4 hours and then stirred at RT overnight. The reaction mixture was quenched by pouring into vigorously stirring water (600 ml) containing sodium hydrogencarbonate (1 10 g). The dark brown mixture was extracted with DCM (3 x 200 ml) and the organic phase was washed with water (200 ml) and brine (100ml), dried (MgS04) and concentrated under reduced pressure to afford the title product as a brown oil. H-NMR: [400MHz, CDCI3, ? 8.87 (1 H, d, J = 1.4Hz, ArH), 8.39 (1 H, d, J = 1 .9Hz, ArH).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,33252-64-1, 3-Nitro-5-(trifluoromethyl)pyridin-2(1H)-one, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; LEGRAND, Darren Mark; WO2013/38373; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem