Pyridine-derivatives

Application of 1628-89-3, 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. 1628-89-3, name is 2-Methoxypyridine, molecular formula is C6H7NO, 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 procedure: A stirred cooled (0 C) solution of LiTMP prepared at 0 C in THF (6 mL) from 2,2,6,6-tetramethylpiperidine (1.7 mL, 10 mmol) and BuLi (1.6 M hexanes solution, 10 mmol) was treated with TMEDA (0.77 mL, 5.0 mmol) and CuCl (495 mg, 5.0 mmol). The mixture was stirred for 15 min at 0 C before introduction of the required substrate (5 mmol). After 2 h at rt, a solution of the required aroyl chloride (10 mmol) in THF (3 mL) was added. The mixture was stirred at rt or 60 C overnight before addition of a 1 M aqueous solution of NaOH (20 mL) and extraction with Et2O (220 mL). After washing the organic phase with an aqueous saturated solutionof NH4Cl (10 mL) and drying over anhydrous Na2SO4, the solvent was evaporated under reduced pressure, and the product was isolated after purification by flash chromatography on silica gel (the eluent is given in the product description).

According to the analysis of related databases, 1628-89-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Marquise, Nada; Harford, Philip J.; Chevallier, Floris; Roisnel, Thierry; Dorcet, Vincent; Gagez, Anne-Laure; Sable, Sophie; Picot, Laurent; Thiery, Valerie; Wheatley, Andrew E.H.; Gros, Philippe C.; Mongin, Florence; Tetrahedron; vol. 69; 47; (2013); p. 10123 – 10133;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 34107-46-5 ,Some common heterocyclic compound, 34107-46-5, molecular formula is C7H9NO, 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.

Chromium trioxide (11.5 g) is slowly added to 170 ml of pyridine at 20C, and 10 g of the crude 5-hydroxy-methyl-2-methylpyridine in 70 ml of pyridine is added in one portion to the complex. The temperature is raised to reflux temperature for 2 hours, and the mixture is refluxed for 1.5 hours. After cooling, 250 ml of water is added, and the mixture is extracted with five 150-ml portions of diethyl ether. The combined extracts are dried over magnesium sulfate and concentrated to give 4.2 g of crude 6-methyl-3-pyridinecarbaldehyde.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,34107-46-5, its application will become more common.

Reference:
Patent; Dainippon Pharmaceutical Co., Ltd.; EP210782; (1991); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1032943-41-1, 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. 1032943-41-1, name is 4-Bromo-1-methyl-1H-pyrazolo[3,4-c]pyridine, molecular formula is C7H6BrN3, 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 Procedure 3 (GP 3): Suzuki coupling (Conditions A); The heteroaryl halide (1 eq), the respective aryl pinacolato boronate or aryl boronic acid (1.2 to 1.5 eq.) and Pd(PPh3)4 (6 mol%) were weighed into a Biotage microwave vial and capped. Toluene (6 mL per mmol halide), EtOH (6 mL per mmol halide) and 1M aq. Na2CO3 solution (2 eq.) were added by syringe. The resulting mixture was prestirred (10 sec) and subsequently heated to 120 C for 15 min (fixed hold time) in a Biotage Initiator microwave reactor. The reaction mixture was diluted with water and ethyl acetate, the layers were separated and the aqueous layer extracted with ethyl acetate. The combined organic layers were dried and concentrated in vacuo. The residue was optionally purified by flash column chromatography and/or trituration and/or preparative HPLC.; Intermediate 3.1; Preparation of 4-(1-Methyl-1 H-pyrazolo[3,4-c]pyridin-4-yl)-phenylamine; [Show Image] In analogy to GP 3, 1.06 g of Intermediate 2.1 (5 mmol, 1 eq.), 1.31 g of 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine (6 mmol, 1.2 eq.) and 347 mg Pd(PPh3)4 (6 mol%) were weighed into a Biotage microwave vial and capped. 30 mL toluene, 30 mL EtOH and 1M aq. Na2CO3 solution (9.65 mL, 1.9 eq.) were subsequently added by syringe. The resulting mixture was prestirred (10 sec) and subsequently heated to 120 C for 15 min (fixed hold time) in a Biotage Initiator(at) microwave reactor. The reaction mixture was diluted with water and ethyl acetate, the layers were separated and the aqueous layer extracted with ethyl acetate. The combined organic layers were dried and concentrated in vacuo to yield after trituration 701 mg of the desired product (3.13 mmol, 63% yield), which was used for subsequent transformations without further purification. 1H-NMR (d6-DMSO; 400 MHz): 8.97 (s, 1 H); 8.24 – 8.25 (m, 2 H); 7.46 (d, 2 H); 6.69 (d, 2 H); 5.40 (br. s, 2 H); 4.15 (s, 3 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 1032943-41-1, 4-Bromo-1-methyl-1H-pyrazolo[3,4-c]pyridine.

Reference:
Patent; Bayer Schering Pharma Aktiengesellschaft; EP1932845; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 153034-86-7 ,Some common heterocyclic compound, 153034-86-7, molecular formula is C5H3ClIN, 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.

Step 1 To a solution of 2-cyclopentenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (681 mg, 3.51 mmol) and 2-chloro-4-iodopyridine (700 mg, 2.92 mmol) in 1,4-dioxane (12 mL) was added 2.0 M aqueous Na2CO3 (4.39 mL, 8.77 mmol) and tetrakis(triphenylphosphine)palladium(0) (67.6 mg, 0.059 mmol). The reaction mixture was heated at 90 C. for 3.5 h then cooled to room temperature, diluted with water and extracted with EtOAc (2*). The combined organics were dried over MgSO4 and concentrated. The residue was purified by silica gel chromatography (0% to 10% EtOAc/hexanes) to afford 450 mg (86%) of 2-chloro-4-cyclopent-1-enyl-pyridine as a white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,153034-86-7, its application will become more common.

Reference:
Patent; Hendricks, Robert Than; Hermann, Johannes; Kondru, Rama; Lou, Yan; Lynch, Stephen M.; Owens, Timothy D.; Soth, Michael; US2011/230462; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 89937-77-9, Methyl 1,2-dihydro-2-oxopyridine-4-carboxylate, 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, 89937-77-9, blongs to pyridine-derivatives compound. COA of Formula: C7H7NO3

Step 1 4-Hydroxymethyl-1H-pyridin-2-one 2-Oxo-1,2-dihydropyridine-4-carboxylic acid methyl ester (1.8 g, 12.2 mmol), prepared as described in J. Org. Chem., 26, 428 (1961), was suspended in THF(100 ml). A small amount of DMF was added to help increase solubility. LiBH4 (61 mmol) was added and the reaction was stirred for 18 hours at room temperature. MeOH and H2 O are added to quench the reaction. The reaction is then concentrated to yield a yellow oil. Flash chromatography (5% MeOH/CHCl3 to 20% MeOH/CHCl3) yielded 4-hydroxymethyl-1H-pyridin-2-one as a white solid. 1 H NMR (400 MHz, CD3 OD) delta 7.38-7.36 (1H,d); 6.56 (s, 1H); 6.37-6.36 (d, 1H); 4.50 s, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,89937-77-9, its application will become more common.

Reference:
Patent; Merck & Co., Inc.; US6093737; (2000); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 96530-81-3, 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 96530-81-3, name is 4-Fluoro-2-methoxypyridine. This compound has unique chemical properties. The synthetic route is as follows.

INTERMEDIATE 24 4-(3-Iodo-l H-pyrazol- 1 -yl)-2-methoxypyridine To 3-iodo-lH-pyrazole (763 mg, 3.93 mmol) in DMSO (15 mL) at 0 C, was added sodium hydride (60% in mineral oil, 189 mg, 4.72 mmol). The reaction was warmed to 25 C and stirred for 60 min before 4-fluoro-2-methoxypyridine (500 mg, 3.93 mmol) was added. The reaction mixture was stirred at 90 C for 4.5 h before quenching by the addition of water. The reaction mixture was extracted with EtOAc. The combined organic extracts were dried over MgS04 and concentrated in vacuo. The crude mixture was purified by flash chromatography (ISCO Combiflash, 0-30% EtOAc in hexanes) to afford 4-(3-iodo-17J-pyrazol-l-yl)-2-methoxypyridine, as a white solid. LCMS calc. = 301.97; found = 302.02 (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 96530-81-3, 4-Fluoro-2-methoxypyridine.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MOCHIDA PHARMACEUTICAL CO., LTD.; SMITH, Cameron, James; TAN, John, Qiang; ZHANG, Ting; BALKOVEC, James; GREENLEE, William, John; GUO, Liangqin; XU, Jiayi; CHEN, Yi-heng; CHEN, Yili; CHACKALAMANNIL, Samuel; HIRABAYASHI, Tomokazu; NAGASUE, Hiroshi; OGAWA, Kouki; WO2014/120346; (2014); 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.73781-91-6, name is Methyl 6-chloronicotinate, molecular formula is C7H6ClNO2, molecular weight is 171.58, as common compound, the synthetic route is as follows.Quality Control of Methyl 6-chloronicotinate

Reference example 56:; 2-Amino-N-(5-methoxycarbonyl-2-pyridyl)-2-methyl-amine [0263] To a solution of methyl 6-chloronicotinate (3.42 g, 20.0 mmol) in 2-propanol(20 mL) were added diisopropylethylamine (4.18 mL, 24.0 mmol) and 1,2-diamino-2-methylpropane (3.14 mL, 30.0 mmol), and the mixture was refluxed at 80 DEG C for 48 hours. The reaction mixture was concentrated under reduced pressure, and chloroform and aqueous potassium carbonate solution were added to the residue. The aqueous layer was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (Chromatorex (registered trademark) NH, Fuji Silysia, hexane/ethyl acetate =5/1) to obtain the title compound (2.31 g, 10.3 mmol).yield: 52%<1>H NMR (CDCl3) delta (ppm): 8.71 (1H, d, J = 2.3 Hz), 7.95 (1H, dd, J = 8.9, 2.3 Hz), 6.40 (1H, d, J = 8.9 Hz), 5.53 (1H, t, J = 5.9 Hz), 3.86 (3H, s), 3.27 (2H, d, J = 5.9 Hz), 1.30 (2H, br s), 1.18 (6H, s).APCIMS (m/z): 224 (M + H)<+>

At the same time, in my other blogs, there are other synthetic methods of this type of compound,73781-91-6, Methyl 6-chloronicotinate, and friends who are interested can also refer to it.

Reference:
Patent; KYOWA HAKKO KOGYO CO., LTD.; EP1354882; (2003); 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. 65-22-5, name is 3-Hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde hydrochloride, molecular formula is C8H10ClNO3, 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. Safety of 3-Hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde hydrochloride

To a solution of 0.25 mmol (0.036 g) triethylenetetramine in10 mL methanol, 0.5 mmol (0.1 g) of pyridoxal chloridrate and1.3 mmol (136 mL) triethylamine were added. The solution was heated in an oil-bath at 55 C and stirred by 15 min. Then a solution of 0.25 mmol (0.091 g) of Ni(ClO4)26H2O in 5 mL methanol was dropped to the main solution, which was stirred at 55 C by 1 h. The slow evaporation of the solvent afforded orange crystals after 4days. A similar one-pot synthesis was already reported [13].Yield: 65%. Melting point: 118e119 C. Anal. Calc: C22H34N6O6Ni:C, 49.19; H, 6.33; N,15.65. Found: C, 49.12, H, 6.39; N,15.44%. IR (KBrpellets, cm1): 3526 [m, n(OeH)alcohols]; 3302 [m, n(OeH)alcohol];2921 [w, n(CeH)sp3)]; 1637 [s, n(C]N)]; 1312 [m, n(OeH)alcohol]1263 [m, n(CeO)phenol.]; 1201[s, n(CleO)percholate]; 1012 [s,n(CeO)alcohols].

With the rapid development of chemical substances, we look forward to future research findings about 65-22-5.

Reference:
Article; Back, Davi Fernando; De Oliveira, Gelson Manzoni; Fontana, Liniquer Andre; Ramao, Brenda Fiorin; Roman, Daiane; Iglesias, Bernardo Almeida; Journal of Molecular Structure; vol. 1100; (2015); p. 264 – 271;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 115473-15-9, 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. 115473-15-9, name is 5,6,7,7a-Tetrahydrothieno[3,2-c]pyridin-2(4H)-one hydrochloride. A new synthetic method of this compound is introduced below.

Under nitrogen protection,A solution of 25.7 g (100 mmol) of 1-cyclopropyl-2-bromo-2- (2-fluorophenyl)2-oxo-2,4,5,6,7-7a-tetrahydrothieno [3,2-c] pyridine hydrochloride (28.7 g, 150 mmol)73 g (30 mmol) of cuprous iodide,Xphos 28.6 g (60 mmol), sodium carbonate 42.4 g (400 mmol) in 250 ml reaction flask, in 200 ml of 1,4-dioxane60 C for 3 hours. After the reaction, the mixture was cooled to room temperature, poured into ice water, extracted with methylene chloride, saturated sodium thiosulfateThe organic phase was concentrated and the mixture was recrystallized from dichloromethane and petroleum ether (1: 10) to give 5- (alpha-cyclopropylcarbonyl-2-fluorobenzyl)2-oxo-2,4,5,6,7,7a-tetrahydrothieno [3,2-c] pyridine in a yield of 90.2% and a purity of 99.37%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,115473-15-9, 5,6,7,7a-Tetrahydrothieno[3,2-c]pyridin-2(4H)-one hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; Qingdao Chenda Biological Science & Technology Co., Ltd.; Chen, Linghao; (8 pag.)CN106117240; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 13091-23-1, 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 13091-23-1, name is 4-Chloro-3-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows.

A solution of 4-chloro-3-nitropyridine (1.0 equiv.) and piperidine (2.0 equiv.) in ethanol, at a concentration of 0.5 M, was stirred at rt for 48 hours at which time the ethanol was removed in vacuo. The residue was partitioned between EtOAc (300 mL) and Na2CO3 (Sat) (75 mL), was washed further with H2O (50 mL), NaCl(Sat ) (50 mL), was dried over MgSO4, was filtered and the volatiles were removed in vacuo yielding 3- nitro-4-(piperidin-l-yl)pyridine (95%). LCMS (m/z): 207.7 (MH+); LC Rt = 1.60 min. 1H NMR (CDCl3): delta 8.80 (s, IH), 8.31 (d, J=5.7, IH), 6.84 (d, J=6.3, IH), 3.18-3.21 (m, 4H), 1.64-1.78 (m, 6H).

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 13091-23-1, 4-Chloro-3-nitropyridine.

Reference:
Patent; NOVARTIS AG; WO2009/109576; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem