Pyridine-derivatives

Synthetic Route of 1152617-24-7 ,Some common heterocyclic compound, 1152617-24-7, molecular formula is C5H4ClIN2, 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.

To a mixture of Z l7c (6.95 kg, assay 72%, 27.23 mol) in l,4-dioxane (72 L) was added Xantphos (233 g, 41 1 mmol, 0.015 eq), Pd2(dba)3 (186 g, 206 mmol,0.0075eq), Z l7b (7.13 kg, 28.02 mol) and DIPEA (7.02 kg, 54.46mol). The system was vacuated and purged with nitrogen gas three times. The mixture was stirred at 65 C for 16 h under N2. The mixture was cooled to rt and water (50 L) was added, filtered. The cake was washed with EA (25L). The filtrate was extracted with EA (4 x 20 L). The organic phase was concentrated in vacuum to offer the crude product which was combined with the cake. Then DCM (60 L) was added to the crude product and stirred at 25-30C for 18h and then filtered. The filter cake was slurried with CH2CI2 (30 L) for 4 hrs and filtered. The filter cake was slurred in CH2CI2 (30 L) for 16 hrs and filtered. Then the filter cake was dried in vacuum to give Z17a (9.1 kg, 84 %) as light yellow solid. NMR (400 MHz, DMSO-d6)5 = 7.89 (s, 1H), 7.7 (d, J = 7.6 Hz, 1H), 7.18 (bs, 2H), 6.40 (bs, 2H), 5.97 (d, J = 7.6 Hz, 1H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1152617-24-7, its application will become more common.

Reference:
Patent; NOVARTIS AG; FEI, Zhongbo; ZHANG, Hao; JIA, Huanqing; WANG, Hui; WANG, Jianhua; LI, Wei; LIN, Xiaohui; MIN, Zhongcheng; (91 pag.)WO2020/65452; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 131803-48-0, 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. 131803-48-0, name is Methyl 6-(bromomethyl)nicotinate, molecular formula is C8H8BrNO2, 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.

Methyl 6-(anilinomethyl)pyridine-3-carboxylate hydrochloride (I-30) A mixture of N-Boc-aniline (350 mg, 1.81 mmol) and methyl 6-(bromomethyl)pyridine-3-carboxylate (500 mg, 2.17 mmol) in THF (10 mL) at 0 C. was added with sodium hydride (108 mg, 60% dispersion in mineral oil, 2.71 mmol). The reaction was stirred for 1 h at room temperature was then heated at 60 C. for 5 h. The reaction was cooled to room temperature and quenched with water. The mixture was partitioned between ethyl acetate and saturated aqueous ammonium chloride solution. The organic phase was washed with brine, dried over MgSO4 then evaporated to dryness. The residue was taken up with 4N solution of HCl in dioxane (5.5 mL) and the resulting mixture was stirred at room temperature for 2 h. The reaction was concentrated under reduced pressure and the residue was triturated with diethyl ether to provide the title compound (394 mg, 78%) as an off-white solid. 1H NMR (400 MHz, DMSO): delta 9.07 (d, J=2.0 Hz, 1H), 8.33 (dd, J=2.0, 8.0 Hz, 1H), 7.59 (d, J=8.4 Hz, 1H), 7.14-7.10 (m, 2H), 6.74-6.70 (m, 3H), 4.54 (s, 2H), 3.88 (s, 3H), NH not observed.

According to the analysis of related databases, 131803-48-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CHIESI FARMACEUTICI S.P.A.; AMARI, Gabriele; ARMANI, Elisabetta; GHIDINI, Eleonora; BAKER-GLENN, Charles; VAN DE POEL, Herve; WHITTAKER, Ben; US2015/158858; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1256810-58-8, 6-Bromo-3-chloro-2-methoxypyridine, 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, Recommanded Product: 6-Bromo-3-chloro-2-methoxypyridine, blongs to pyridine-derivatives compound. Recommanded Product: 6-Bromo-3-chloro-2-methoxypyridine

Reference Example 4-15 (5R)-5-[(5-Chloro-6-methoxypyridin-2-yl)ethynyl]-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one (5R)-1-(2,4-Dimethoxybenzyl)-5-ethynylpyrrolidin-2-one (600 mg, synthesized according to Tetrahedron Asymmetry, 1995, 239 using dimethyl (R)-glutamate hydrochloride as a raw material) in acetonitrile (6 mL) was added to a solution of 6-bromo-3-chloro-2-methoxypyridine (667 mg), bis(triphenylphosphine)palladium(II) dichloride (81 mg) and copper iodide (22 mg) in triethylamine (12 mL) in a nitrogen gas stream at 40 C. over 30 minutes. The mixture was stirred at room temperature for four hours. The reaction solution was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1?0:1) to give the title compound as a colorless oil (452 mg, 52%). 1H NMR (300 MHz, CDCl3) delta ppm 2.12-2.48 (m, 3H), 2.53-2.70 (m, 1H), 3.79 (s, 3H), 3.80 (s, 3H), 4.04 (s, 3H), 4.26 (d, J=15 Hz, 1H), 4.37-4.46 (m, 1H), 4.89 (d, J=15 Hz, 1H), 6.38-6.49 (m, 2H), 6.94 (d, J=7.8 Hz, 1H), 7.18-7.25 (m, 1H), 7.57 (d, J=7.8 Hz, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1256810-58-8, 6-Bromo-3-chloro-2-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD; NISSAN CHEMICAL INDUSTRIES, LTD.; US2011/237791; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1065267-14-2, (3,5-Difluoropyridin-2-yl)methanol, 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, 1065267-14-2, blongs to pyridine-derivatives compound. category: pyridine-derivatives

(3,5-Difluoropyridin-2-yl)methyl 4-methylbenzenesulfonate (I-5)To a solution of (3,5-difluoropyridin-2-yl)methanol (0.25 g, 0.7 mmol) in tetrahydrofuran (THF; 10 mL) was added potassium hydroxide (KOH; 0.14 g, 2.55 mmol) at RT, and the mixture was stirred for 15 min p-Toluenesulfonyl chloride (0.42 g, 2.21 mmol) was added slowly at RT, and the reaction mixture was stirred for another 18 h. After complete consumption of the starting material (by TLC), the reaction mixture was diluted with H2O (50 mL) and extracted with EtOAc (2×25 mL). The combined organic extracts were washed with H2O (25 mL) and brine (25 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure to obtain the crude material. Purification by silica gel column chromatography eluting with 15% EtOAc/hexane afforded compound I-5 (0.18 g, 0.25 mmol, 35%) as colorless liquid. 1H NMR (500 MHz, CDCl3): delta 8.29 (s, 1H), 7.82 (d, J=8.5 Hz, 2H), 7.34 (d, J=8.5 Hz, 2H), 7.20-7.16 (m, 1H), 5.20 (s, 2H), 2.45 (s, 3H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1065267-14-2, its application will become more common.

Reference:
Patent; Viamet Pharmaceuticals, Inc.; US2012/329788; (2012); 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. 53937-02-3, name is 4-Benzyloxy-2-(1H)-pyridone. A new synthetic method of this compound is introduced below., Recommanded Product: 4-Benzyloxy-2-(1H)-pyridone

A mixture of N,N-diethyl-7-iodopyrazolo[1,5-a]pyridin-3-amine (0.25 g, 0.79 mmol), 4-benzyloxy-2(1H)-pyridone (0.19 g, 0.94 mmol), copper(1) iodide (0.003 g, 0.016 mmol) and potassium carbonate (0.13 g, 0.94 mmol) in DMF (5.0 ML) was heated at 150 C. for 3 h and cooled down to room temperature.The mixture was partitioned between EtOAc and H2O and separated.The organic layer was concentrated in vacuo to dryness.The residue was subjected to column chromatography (E:H=1:4) to give 0.18 g (60%) of a clear oil as the title compound: 1H NMR (400 MHz, CDCl3) delta 7.96 (d, J=5.8 Hz, 1H), 7.81 (s, 1H), 7.48-7.43 (m, 6H), 7.12-7.08 (m, 1H), 6.80 (s, 1H), 6.74 (d, J=5.8 Hz, 1H), 6.59 (d, J=6.4 Hz, 1H), 5.19 (s, 2H), 3.14 (q, J=7.1 Hz, 4H), 1.06 (t, J=7.1 Hz, 6H); MS (EI) m/z 389.25 (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, 53937-02-3, 4-Benzyloxy-2-(1H)-pyridone.

Reference:
Patent; Fu, Jian-Min; US2004/2511; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 15862-34-7, Adding some certain compound to certain chemical reactions, such as: 15862-34-7, name is 5-Bromo-2-hydroxy-3-nitropyridine,molecular formula is C5H3BrN2O3, 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 15862-34-7.

To a round-bottom flask charged with 5-Bromo-3-nitro-pyridin-2-ol (976 mg, 4.0 mmol) was added 6.0 mL of phosphoryl chloride, the resulting suspension was heated to 105 0C and kept for 12 hrs. Then the excess POCI3 was removed under reduced pressure, the residue then was dissolved in anhydrous 10 mL of DCM, 1 mL of 3-aminopropyl-1-ol was then added. The resulting mixture was stirred for 30 min., DCM was then removed under reduced pressure to give a oil residue which was stirred at 45 0C for 12 hrs. Then the reaction was quenched with water, extracted with ethyl acetate, washed with brine and dried over sodium sulfate. After removal of solvent, the residue was obtained as a yellow solid 3-(5-bromo-3-nitro-pyridin-2-ylamino)-propan-1-ol and was used for next step without further purification. 1H NMR (400 MHz, CDCI3) delta 1.90 (2H, m), 2.60 (1 H, br.), 3.71 (2H, m), 3.78 (2H, m), 8.42 (1 H, d, J = 2.4 Hz), 8.55 (1 H, d, J = 2.4 Hz); MS m/z (MH)+: 276, 278

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. 15862-34-7, 5-Bromo-2-hydroxy-3-nitropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; S*BIO PTE LTD; YU, Niefang; WO2006/101456; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 286946-77-8 ,Some common heterocyclic compound, 286946-77-8, molecular formula is C5H3BrClNO, 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.

To a solution of 65 5-bromo-2-chloropyridin-3-ol (50.2 g, 241 mmol) in 56 N,N-dimethylformamide (200 mL) were added successively 66 benzyl bromide (33.0 mL, 278 mmol) and 67 potassium carbonate (48.6 g, 352 mmol), and the mixture was stirred at room temperature for 4 hr. To the reaction solution was added 14 water (600 mL), and the mixture was stirred for 2 hr. The precipitate was collected by filtration, and dried under reduced pressure to give 68 3-(benzyloxy)-5-bromo-2-chloropyridine (69.7 g, yield 96%). 1H-NMR (DMSO-D6) delta: 5.29 (2H, s), 7.33-7.47 (5H, m), 7.98 (1H, d, J=2.1 Hz), 8.14 (1H, d, J=1.8 Hz)

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. 286946-77-8, 5-Bromo-2-chloropyridin-3-ol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JAPAN TOBACCO INC.; NAGAMORI, Hironobu; NISHIMARU, Tatsuya; TAKAGI, Masaki; MITANI, Ikuo; NAKAGAWA, Yuichi; US2019/152926; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 75806-84-7 ,Some common heterocyclic compound, 75806-84-7, molecular formula is C6H2BrClF3N, 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.

Preparation Example 1 Ten grams of 2-bromo-3-chloro-5-trifluoromethylpyridine was dissolved in 100 ml of dry diethyl ether in a nitrogen stream, and the resulting solution was cooled to -78 C. To the solution thus cooled was gradually dropwise added 30 ml of a 15% solution of n-butyl lithium in hexane, and the resulting mixture was stirred at that temperature for 30 minutes. Thereafter, an excessive amount of pulverized dry ice was gradually introduced into the solution. The temperature of the solution was returned to room temperature, and the solution was stirred at that temperature for an additional 1 hour. After the reaction was completed, 100 ml of water was added to thereby subject to the extraction. An aqueous layer thus formed was isolated and made acidic by adding thereto concentrated hydrochloric acid to form an oily product. The thus formed oily product was extracted with 300 ml of methylene chloride. After drying an organic layer over anhydrous sodium sulfate, the solvent was evaporated off under reduced pressure to obtain 5.1 g of 3-chloro-5-trifluoromethylpyridine-2-carboxylic acid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,75806-84-7, its application will become more common.

Reference:
Patent; Ishihara Sangyo Kaisha, Ltd.; US4367336; (1983); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 15506-18-0, 1-Methyl-2-oxo-1,2-dihydropyridine-3-carboxylic acid, 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

[0625] To a solution of 2-(4-(2,4-difluorophenoxy)piperidin-l-yl)-5- (etaiotaomicronphi1etaomicron8Homicronetanu1)rhonupieta-3-3etapietaepsilon (50.00 mg, 1 10.0 muiotaetaomicron, 1.00 eq) and 1 -methyl -2 -oxo- 1,2- dihydropyridine-3-carboxylic acid (20.22 mg, 132.0 mutauetaomicron, 1.20 eq) in DMF (2 mL) was added HATU (62.75 mg, 165,02 muiotaetaomicron, 1.50 eq) and DIPEA (42.65 mg, 330.0 muetaiotaomicron, 57.64 mu,, 3.00 eq). The resulting mixture was stirred at 25C for 12 hours, then diluted with EtOAc (50 mL) and washed with saturated aq N’a >(*<) > (20 rnL) and brine (20 mL). The organic layers were dried over anhydrous NazSC filtered, concentrated in vacuo, and purified by preparative HPLC (basic mode) to give the title compound as a white solid (18 mg, 27%). .H NMR (400 MHz, CDCb) delta ppm 2.09 – 2.27 (m, 4 H), 3.01 – 3.15 (m, 4 H), 3.15 – 3.24 (m, 2 H), 3.54 – 3.63 (m, 2 H), 3.72 (s, 3 H), 3.75 – 3.85 (m, 4 H), 4.42 (dt,./ 7. 1. 3.5 Hz, 1H), 6.49 (t,./ 7. 1Hz, 1H), 6.74 – 6,83 (m, 1 I D. 6.87 (ddd, J=l 1.0, 8.4, 3.1Hz, 1H), 7.03 (td,,7=9.2, 5.5 Hz, 1H), 7.64 (dd, J=6.6, 1.8 Hz, 1H), 8.43 (d, J=2.2 Hz, 1H), 8.60 (dd, J=7.3, 2.0 Hz, 1H), 9.07 (d, J=2.2 Hz, 1H), 12.23 (s, 1H); ESI-MS m/z] M · Pi | 590.0.

The synthetic route of 15506-18-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; GREEN, Jason; HOPKINS, Maria; JONES, Benjamin; KIRYANOV, Andre A.; KUEHLER, Jon; MONENSCHEIN, Holger; MURPHY, Sean; NIXEY, Thomas; SUN, Huikai; (300 pag.)WO2018/183145; (2018); 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. 105250-17-7, name is (2-Aminopyridin-4-yl)methanol, molecular formula is C6H8N2O, 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 (2-Aminopyridin-4-yl)methanol

To a stirred solution of 67 (1.39 g, 11.2 mmol) in EtOH (46.5 ml)-water (6.5 ml) was added NaHCO3 (1.88 g, 22.3 mmol), followed by a 50percent w/w aqueous solution of chloroacetaldehyde (2.84 ml, 1.75 g, 22.4 mmol). The resultant suspension was stirred and refluxed for 2 h. The dark amber-colored reaction mixture was carefully concentrated (frothing) under reduced pressure to approximately half its original volume and then filtered. Collected solid was washed with MeOH. Combined filtrate and washings were concentrated in vacuo and yielded a dark, oily two-phase mixture. Treatment with EtOH produced a mixture of solid precipitate and a homogeneous liquid phase, which was filtered. The filtrate was concentrated under reduced pressure to a dark oil, which was purified via flash chromatography on silica gel, eluting with CH2CI2-CH3OH -NH4OH (91.5:8.5:0.25), to obtain compound 68 as a pale yellow solid (1.34 g; 80percent). To a solution of 68 (1.20 g, 8.10 mmol) in MeOH (5 ml) was added acetone (48 ml). A small amount of dark precipitate formed and was removed by filtration (0.45 muM syringe filter). To the clear yellow filtrate was added via syringe 1 M ethereal HCI (8.1 ml, 8.1 mmol). The resultant mixture was stirred briefly and was then filtered. The hygroscopic solid thus isolated was washed rapidly with acetone and dried under vacuum at 50 0C to obtain the hydrochloride salt of 68 as a tan powder (1.34 g; 89percent). EPO

With the rapid development of chemical substances, we look forward to future research findings about 105250-17-7.

Reference:
Patent; SCHERING CORPORATION; WO2007/1975; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem